Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
House in Berkshires, MA
9 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
About this house rental
Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests.
The rarest of New England homes, with historic bones and bright contemporary additions, August Moon sits on 88 acres of private and peaceful land in the heart of the Berkshires with mountain views from various parts of the property. Just steps away from beautiful hiking trails, it features a perfect blend of new and old, urbane and rustic, and with an eternal quality that is felt throughout the home and the vast property. Enjoy western views of Mount Race and Mount Everett from the grounds, or explore the walking trail through the woods. The trailhead to Racebrook Falls can be accessed by walking down the dirt road where the house is located.
With 3100 sq. ft of wood floors and cozy decor, this spacious house was renovated with two additions: sunroom with master bedroom above, and a gourmet kitchen. The original portion of the house includes a den with fireplace and 42" plasma tv with satellite surround sound home theater system. Built-in bookshelves have loads of great reading and an eclectic DVD library that should have something for everyone. The Parlor is a wood-paneled room with a wood-burning stove, opening up to a small deck with Adirondack chairs for lounging. This is a great room for entertaining with a stereo, turntable, and vinyl record collection. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a candle fireplace.
A bright sunroom opens up to a back patio with teak outdoor furniture, an umbrella, and vast flower gardens that bloom in every season.
In the Master Suite, wake up to beautiful mountain views particularly spectacular during fall foliage season, and go to bed relaxed after taking a soak in the private master bath jacuzzi. Bath and shower products and candles along with luxurious bath robes complete the experience. Vaulted ceilings, cherry hardwood floors, and walk-around deck make this room a relaxing retreat. All bedrooms feature down comforters, high thread count sheets and fans. All bathrooms feature hair dryers, robes, plush towels, Shampoo, Conditioner and Shower Gel.
Bedrooms: In addition to the spacious master, there are three guestrooms with great architectural details like original wood beams and hardwood floors. The upstairs landing with skylights and gas stove features a day bed perfect for reading in the afternoon.
Kitchen: The gourmet kitchen features top-notch equipment like a WOLF eight-burner stove and is fully stocked with cookware, utensils, barware, dishware and other essential cooking tools. A secondary kitchen with another refrigerator makes entertaining for larger groups easy.
Flower gardens are in abundance and you will be enticed to the hammock to unwind and soak in the incredible mountain views. After playing a round of tennis on the clay court, enjoy a glass of iced-tea on the outdoor porch furniture at the tennis house bar. Or retreat to the shaded seated area behind the cutting garden or shady hideaway under the canopy of the weeping Katsura tree.
Other amenities include: walking trails, tennis court, two fireplaces, wood-burning stove, gas stove, air conditioning in the tv room, master suite, sunroom, and kitchen. WI-FI, cable HDTV, DVD, VCR, stereo, CDs, Jacuzzi tub, microwave, dishwasher, linens, washer/dryer. The three-story garage features a ping-pong and pool table game room on the 2nd story. In the garage, find bikes and helmets for kids and adults, and loads of outdoor games like bocce, croquet, corn hole, badminton, and more. A kids' outdoor playhouse and secret playroom in the twin bedroom are great places for the little ones to play.
Smoking is **strictly not permitted.** Large Parties are prohibited.
*** No Longer accepting Wedding Inquiries.
Keywords: skiing, snow, fall foliage, tanglewood, berkshires, mountains, hiking, tennis, peace, privacy, country roads, escape, country living.
The rarest of New England homes, with historic bones and bright contemporary additions, August Moon sits on 88 acres of private and peaceful land in the heart of the Berkshires with mountain views from various parts of the property. Just steps away from beautiful hiking trails, it features a perfect blend of new and old, urbane and rustic, and with an eternal quality that is felt throughout the home and the vast property. Enjoy western views of Mount Race and Mount Everett from the grounds, or explore the walking trail through the woods. The trailhead to Racebrook Falls can be accessed by walking down the dirt road where the house is located.
With 3100 sq. ft of wood floors and cozy decor, this spacious house was renovated with two additions: sunroom with master bedroom above, and a gourmet kitchen. The original portion of the house includes a den with fireplace and 42" plasma tv with satellite surround sound home theater system. Built-in bookshelves have loads of great reading and an eclectic DVD library that should have something for everyone. The Parlor is a wood-paneled room with a wood-burning stove, opening up to a small deck with Adirondack chairs for lounging. This is a great room for entertaining with a stereo, turntable, and vinyl record collection. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a candle fireplace.
A bright sunroom opens up to a back patio with teak outdoor furniture, an umbrella, and vast flower gardens that bloom in every season.
In the Master Suite, wake up to beautiful mountain views particularly spectacular during fall foliage season, and go to bed relaxed after taking a soak in the private master bath jacuzzi. Bath and shower products and candles along with luxurious bath robes complete the experience. Vaulted ceilings, cherry hardwood floors, and walk-around deck make this room a relaxing retreat. All bedrooms feature down comforters, high thread count sheets and fans. All bathrooms feature hair dryers, robes, plush towels, Shampoo, Conditioner and Shower Gel.
Bedrooms: In addition to the spacious master, there are three guestrooms with great architectural details like original wood beams and hardwood floors. The upstairs landing with skylights and gas stove features a day bed perfect for reading in the afternoon.
Kitchen: The gourmet kitchen features top-notch equipment like a WOLF eight-burner stove and is fully stocked with cookware, utensils, barware, dishware and other essential cooking tools. A secondary kitchen with another refrigerator makes entertaining for larger groups easy.
Flower gardens are in abundance and you will be enticed to the hammock to unwind and soak in the incredible mountain views. After playing a round of tennis on the clay court, enjoy a glass of iced-tea on the outdoor porch furniture at the tennis house bar. Or retreat to the shaded seated area behind the cutting garden or shady hideaway under the canopy of the weeping Katsura tree.
Other amenities include: walking trails, tennis court, two fireplaces, wood-burning stove, gas stove, air conditioning in the tv room, master suite, sunroom, and kitchen. WI-FI, cable HDTV, DVD, VCR, stereo, CDs, Jacuzzi tub, microwave, dishwasher, linens, washer/dryer. The three-story garage features a ping-pong and pool table game room on the 2nd story. In the garage, find bikes and helmets for kids and adults, and loads of outdoor games like bocce, croquet, corn hole, badminton, and more. A kids' outdoor playhouse and secret playroom in the twin bedroom are great places for the little ones to play.
Smoking is **strictly not permitted.** Large Parties are prohibited.
*** No Longer accepting Wedding Inquiries.
Keywords: skiing, snow, fall foliage, tanglewood, berkshires, mountains, hiking, tennis, peace, privacy, country roads, escape, country living.
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Ski in / Ski out
Garden
Family friendly
Map of Berkshires, MA
$$$$
Reviews
5.0
I feel so fortunate that I found this gem for Berkshire graduation weekend! Word to the wise, book in advance as it’s a popular spot!
5.0
A perfect place for our family get together! Almost equidistant from Boston and New York City (and just a bit farther from Philadelphia), August Moon was a wonderful setting to spend time together. We especially loved the size and workability of the kitchen as we cooked together. Having both a "formal" dining room and an eat-in kitchen gave us lots of options to hang out. The living/family rooms, too, were very comfortable and made for a great few days. Being in the Berkshires provides so many fun activities. We were 9 people and had plenty of space in this lovely farmhouse.
5.0
This is the second time we have stayed at this beautiful rural property about 15 minuts from Great Barrington. The host has always been extremely attentive and drove up from NYC to attend to a heater problem when we had trouble. The house is large and fully stocked with every amenity, particularly the kitchen. There are lots of rooms downstairs to be together or separate. The outdoor space is large and well maintained with hiking trials and lots of space for lawn games, including a tennis court. Close to lots of antique shops and good groceries.
Extremely relaxing. My family is already asking when we will go back.
5.0
It is a serene and lovely getaway.
The home is warm and welcoming.
It was perfect!
5.0
This home is beautiful and sparkling clean! Perfect location from our daughter’s wedding venue! The property is gorgeous with a fabulous view! Wish we had more time to spend at the house, it had 2 outdoor sitting areas, tennis court, huge barn with a pool table. The beds were super comfortable, kitchen was state of the art, and numerous rooms for sitting areas. Definitely would return in the future!
4.0
Lovely location. Very responsive host.
5.0
August Moon was the perfect spot to host our Thanksgiving weekend. The kitchen had all the tools we needed, and we loved going on long hikes on the property and nearby. The house is so warm and comfortable and there are endless things to do, from building fires, to listening to records, or playing in games with kids of all ages. Jill was very communicative, and check-in was seamless. I would stay again, perhaps in summer, so that we could enjoy more of the outdoor activities.
5.0
The home and property is everything advertised and so much more. From the minute we entered the driveway and saw the home surrounded by the stunning gardens we knew we were in for a treat. We loved sitting in the Adirondack chairs in the side yard and walking and exploring the large acreage surrounding the home. But then as you set foot inside the house, you discover the treasures in every room of the house. Designed to be comfortable to friend groups, families, couples, this house will please everyone. The kitchen is fully equipped and we enjoyed making breakfast on the griddle of the Wolf Stove, then looking out the gorgeous windows into the garden and yard surrounding us. We loved candlelight dinners in the dining room, all the warmth of this home in the fireplace room. There's a sun room to enjoy in the day and a living room with television for others. The bedrooms are all upstairs and each bed is very comfortable and carefully furnished with quality bedding. This home is so unique; farmhouse but modernized and it has everything. We loved it so much and highly recommend August Moon!
5.0
My (now) husband and I attempted to rent August Moon to share with a bunch of friends in spring 2020, which we obviously had to cancel. Fast forward 1.5 years after eloping in California and having our twins, we decided to have a real wedding celebration with family and friends, and knew August Moon was the perfect spot. The house itself is charming and elegant without feeling too precious to drag in some dirt and grass from the yard. As many wedding guests commented, the grounds are ideal for entertaining with multiple distinct areas to sit or play lawn games. We were able to host a morning brunch, wedding ceremony, cocktails, and reception all in distinct areas, and with plenty of lawn games to spare. The weekend itself felt magical and almost unreal. Many thanks to Jill for accommodating us and for being so responsive whenever questions came up. We can’t make it back soon enough!
5.0
Our extended family of 6 adults and 2 children (1 toddler, 1 infant) spent 10 days at August Moon in late August. The property is lovely, with several seating areas, including an outdoor dining area and a fire pit. There are walking trails through the woods. The kitchen is well-equipped and amply stocked. The beds were very comfortable. There is no air conditioning in 3 of the 4 bedrooms, but as it cooled off in the evening, the fans were enough to keep the rooms comfortable. Jill, our host, answered our questions promptly and was a pleasure to work with.
2.5
Lovely
5.0
Could not have been better
thoroughly enjoyable stay
5.0
LOVED it!!!
August Moon is awesome!! We loved every bit of it, and the property is spectacular. Wish we owned it
5.0
Beautiful Property and Home
We stayed here for the weekend and did not want to leave. The house is a beautiful historic home with all the charm of early American architecture preserved and yet the convenience of a well equipped modern kitchen and a comfy entertainment room have not been overlooked. The style is true to the heritage with modern touches and beautiful art. The property is stunning and private, dozens of acres of fields, garden, flora and fauna to explore on foot and also to be enjoyed from every window. The stars at night are visible as you fall asleep from the master bed. Note, there are no window coverings in most bedrooms which I was worried about initially but it is so dark at night you really don't need them and it was lovely to have the sun wake us gently. Many activities and games for all ages including tennis, a see-saw, tether ball, horseshoes, board games. The stairs are typical of the period and might be more difficult to navigate for someone with decreased mobility. We look forward to a return visit!
5.0
Fantastic for families, relaxing for adults
We had a fantastic time staying at August Moon. My kids literally didn’t stop running around and playing in the multitude of different activities and toys - they were in heaven! The house has kept the old charm while being equipped with literally anything you could want! Beds were super comfortable and all of the rooms were so well set out - each with a different vibe and purpose. Jill was no more than a text away and the advance information for the house was probably the best I have ever received! My husband referred to the house as ‘life goals’ - so I suspect he’ll be asking when we are next going back?!
5.0
Magical place
We had an amazing family vacation in this beautiful place. The kids loved to hide away and play for hours in the secret play room or wonder around the property to discover the enchanted tree house. The kitchen was so well equipped and it was great fun to cook family recipes for a larger group. We would love to come back in the summer when everything is in full bloom. Thank you so much for having us.
5.0
Stunning Getaway!
The house was so beautiful! Every room has so much character, the kitchen is wonderfully stocked and has bowls and pots and pans of every possible size. The master bedroom is truly stunning and waking up to the sunrise over the mountains was perfect. We would certainly go back!
5.0
Great Fall Stay
We had a great weekend with a group of 8 adults, two infants and a dog. The property is in a great location with a ton of space and privacy while being close to things to do.
5.0
Such a special place!!
We got married at august moon and it was the perfect setting for our celebration. The gardens are absolutely gorgeous and the home is cozy, stylish, and very comfortable. Thank you!!
5.0
Sheffield, MA
Terrific place, wonderful host, lovely few days with friends.
5.0
Warm, vibrant and chic!
We held our wedding at August Moon and it was amazing! The property is absolutely stunning. The gardens and grounds are perfectly manicured and the house is top notch. Every room exudes style. Jill and Trey have fabulous and eclectic taste. Most notably, their record collection, which we enjoyed listening to out
on the patio. They were also super accommodating and easy to get in touch with. They provided us with robes, towels, bubble bath, shampoos, conditioners, face wash and lotions - all of which I will be purchasing to keep my house stocked with from now on! Whether you’re looking to host a snazzy event on the lawn (that your guests will rave on and on about), or you’re looking for a quiet place to relax/reset, this is the place to go. Would highly recommend! ***10/10***
5.0
Bucolic Berkshires Escape
Everything was perfect for our family of four. We each had spaces for privacy and the communal spaces were comfortable and well equipped. The location was ideal for hikes to waterfalls, local dining and shopping. We could not have been any happier with this home. Thank you so much for sharing your special place with us. It will always be a place we will remember.
5.0
As advertised
It is a well-cared for property that abounds with so much possibility. Hosts are great and we will be returning.
2.5
My husband and I had our microwedding here and could not have been more happy with our stay. The scenery is absolutely beautiful in fall, and the house has gorgeous mountain views. All of our guests were in awe of how truly beautiful the landscape was. It was also great for our pup to have ample space to run around.In terms of the house, it was very well decorated and has a very homey, cozy feel. We felt instantly like we lived there! Everything felt very intimate and it was perfect for a small wedding. We truly enjoyed everything about this place and hope we can come back!
5.0
Perfect for microwedding
My husband and I had our microwedding here and could not have been more happy with our stay. The scenery is absolutely beautiful in fall, and the house has gorgeous mountain views. All of our guests were in awe of how truly beautiful the landscape was. It was also great for our pup to have ample space to run around.
In terms of the house, it was very well decorated and has a very homey, cozy feel. We felt instantly like we lived there! Everything felt very intimate and it was perfect for a small wedding. We truly enjoyed everything about this place and hope we can come back!
5.0
Very happy.
Wonderful property, even better than expected!
5.0
Family Weekend
This property is more idyllic than it appears in the photos. You truly feel transported back to a simpler time when staying here. By the same token, the house has every amenity that you could ever want. We had 6 adults and a baby staying here and there was plenty of space for us to lounge. We also did a fair amount of cooking while there and could not believe how well stocked the kitchen was with pots, pans and utensils galore! Jill was an excellent host. We had a slight booking error and she did her absolute best to fix it for us. She was incredibly responsive and informative. The property grounds are vast and we all enjoyed roaming the property. We also enjoyed the fairly easy and quick hike to Race Brook Falls. One of the best parts of our stay was our intimate family dinner at The Stagecoach Tavern. Overall, we had an excellent stay and would highly recommend this property to anyone.
5.0
Amazing house for gatherings and events
This is a beautifully maintained house with lots of history. The spaces are comfortable with excellent decor. The kitchen is well stocked with everything you'll need for a huge feast. It was cold, so we didn't get to use the tennis courts, but the grounds also feature walking trails through a wooded preserve. Stay here!
5.0
Fantastic!
We absolutely loved this property! We usually rent through HomeAway a couple of times each year and this was the best property that we’ve stayed at in all of our experiences over the years. I’ve never wanted to visit a property again, but we will be back for this one. Thank you for sharing a wonderful experience!
5.0
Homey and relaxing
Cozy and nice home in the perfect location for Berkshire mini trips to Lenox, Stockbridge, Great Barrington, Salisbury CT, Millerton NY for a stop at Harney & Sons Tea room, etc. Home is well stocked for cooking, lots of books to read, and ample property to explore. Remember you're in bear country...we were reminded. ;-) Lots of spaces outside to relax and take in the views which are especially nice in the Fall with the mountains as your backdrop. Stagecoach Tavern is walkable from the property or a 2 minute drive if you want a close dinner out but drive to Bistro Box if they're open...worth it! We loved listening to vinyl in the parlor with a fire going in the stove. I'd recommend using that one over the one in the front room which could be a little tricky to keep lit. I know it was mentioned this is a country home and there are some ladybugs. We swept up over 150 in 5 days. Nothing rescreening a few sliders and a little caulk might help with from our investigating. Heads up if you're with a larger group, be aware that the master has no blinds/window coverings so you're open to the side yard if the kiddos are out playing. No wearing your skivvies in front of the windows. Make sure you pull up a seat at night to look out those windows though because the stars are spectacular! Should we find ourselves in the area again, we'll definitely stay here again!
5.0
Great Stsy
My friends and I had a great time at this beautiful old house. Property was so pretty. Only suggestion that I have is I would of preferred blinds or curtains to be able to close at night. Everything else was wonderful
5.0
A magical place
August Moon is not only visually beautiful, it also conveys a warmth and charm that could only come from being a place that has been well loved and cared for over the years. Magical!
5.0
exceptional stay
Sparkling clean ! Cosy, comfortable and quiet retreat. Everything you could ask for!!
Our host was so attentive & friendly. Looking forward to visit again soon :)
5.0
This place is incredible!
We rented August Moon to host our wedding this summer and it was the best decision we could have made. The house and property are gorgeous and it was such a magical, meaningful place to not only have our wedding but to also spend the week relaxing with family and friends. Many of our guests commented on how spectacular the grounds were (the gardens are amazing!) and how peaceful it felt to be there. In addition to the grounds, the house itself is beautiful and cozy. Jill was very communicative and helpful throughout the process. I would highly recommend August Moon for an event, or just as a wonderful woodsy retreat for some R&R. If you have kids, this is also a fantastic rental - my 4 year old nephew may have been the most excited guest at the wedding thanks to the awesome toy room, tree house, and outdoor games.
4.0
A family wonderland
Imagine a place that is beautiful, comfortable, and has everything any member of a multigeneratinal family needs or might want. This is it. The grandkids found the abundance of toys, swings and play spaces magical. Grandma enjoyed stolen private moments in the hammock as well as rocking in it with the baby. Their parents enjoyed the many beautiful outdoor seating areas that allowed for private times as well as family times. The proximity to the Appalachian trail was a big plus for the hikers in the family as was the piano for the musically inclined.
On a hot week the non air conditioned rooms and spaces were very hot. This was only a problem at night as during the day time there were enough cool rooms indoors and shady areas outdoors for everyone to comfortably hang out.
5.0
Beyond Amazing!
The August Moon property was truly a magical setting for our wedding. The house, the grounds, and all the beautiful flowers could not have been a more perfect backdrop for our wedding and guests. Communicating with Jill was incredibly easy and she checked in via text during our stay which was appreciated. Everything exceeded our expectations and we can’t wait to stay there again in the future!
5.0
Beautiful house and property
This was our second stay at August Moon, and it was just as lovely as the first. The house has a beautiful kitchen for baking and cooking, incredible gardens, spacious outdoor seating, a “secret” toy room, and the wonderful ability to play music throughout most rooms. A great visit, all around.
5.0
Magical Wedding Day
August Moon was absolutely gorgeous! We couldn't have asked for a cleaner, more well kept, or magical venue for our wedding. All of our guests raved about how beautiful the property was and my mother just had to call their housekeeper to compliment how clean and tidy the house was.
5.0
Amazing house!
We had a wonderful time at August moon. The house is beautiful, super clean and has everything you need and can think of, and more. And the outside- is just unbelievable. It is the perfect place for families with young children, indoor and outdoor toys, amazing tree house, fire pit- just haven for them. Jill, the host, was very kind and responsive and check in and out was super easy. Prefect place!
5.0
Wonderful family break
Jill's house was absolutely perfect for our family break. Our two young sons found endless enjoyment in the toys both in the house, and outdoors, and loved the space to run. We also took Jill's recommendation and did the hike to Race Brook falls which even our 4 year old could complete. The house was fully equipped and spotlessly clean. One of the best family friendly rentals we have used to date.
FAQs
How much does this house cost compared to others in Berkshires?
The average price for a rental in Berkshires is $294 per night. This rental is $692 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly . For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly ?
We found 13 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.
Explore similar vacation rentals in Berkshires
Explore all rentals in BerkshiresStart earning One Key rewards
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
House
in Lee20 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Nestled in Berkshires, this House is perfect for your next vacation. Enjoy The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
House
in Lee14 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Berkshires? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Spectacular Private Hilltop Contemporary Estate (Pool/Catamount/Bash Bish Fall)
House
in Copake Falls10 guests · 6 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Indulge in a peaceful retreat at Spectacular Private Hilltop Contemporary Estate (Pool/Catamount/Bash Bish Fall), our elegant House in Berkshires. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Luxury Berkshires Retreat in Lenox - Main House
House
in Lenox11 guests · 5 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
This House in Berkshires, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
House
in Great Barrington12 guests · 4 bedrooms · 4 baths
Garden · Pool · Pets allowed
Are you ready to indulge in a relaxing getaway? Our House in Berkshires has everything you need for a rejuvenating stay. Treat yourself to Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!'s exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Perfect setting for Family Vacations Short and Long Term Stays Welcomed.
House
in West Stockbridge10 guests · 5 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Experience the best of Berkshires with this House available for $1,088. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing
House
in Stockbridge24 guests · 12 bedrooms · 8 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing, our elegant House in Berkshires. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
House
in Copake Falls10 guests · 6 bedrooms · 6 baths
Garden · Pool · Pets allowed
Soak up the beauty of Berkshires in our House, Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Start earning One Key rewards
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
House
in Great Barrington16 guests · 5 bedrooms · 4 baths
Ski in / Ski out · Garden · Pets allowed
When traveling to Berkshires, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $905 per night.
$$$$
Berkshires Lake House With Private Dock, gunite pool, and Chefs Kitchen
House
in Canaan12 guests · 6 bedrooms · 3 baths
Garden · Pool · Pets allowed
Looking for the perfect place to call home during your trip to Berkshires? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
House
in Hancock12 guests · 4 bedrooms · 3 baths
Ski in / Ski out · Pool · Kitchen or Kitchenette
Looking for a House in Berkshires, this House for $1,178 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Beautiful Berkshire Farm House on 160+ Acres
House
in Great Barrington16 guests · 7 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
This attractive House in Berkshires, $1,034 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Modern Barn, NEW Luxurious Home
House
in Washington12 guests · 4 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
House in Berkshires, for $919 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
House
in Great Barrington15 guests · 7 bedrooms · 7 baths
Garden · Pets allowed · Kitchen or Kitchenette
This inviting House in Berkshires can fit your needs for many types of vacations, at $880 per night.
$$$$
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
House
in Lanesborough14 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Internet / Wifi
Are you ready to indulge in a relaxing getaway? Our House in Berkshires has everything you need for a rejuvenating stay. Treat yourself to 6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort's exceptional amenities, such as Dishwasher, Fireplace and Internet / Wifi.
$$$$
The Lake House on Lake Waramaug
House
in New Preston12 guests · 5 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
This inviting House in Berkshires can fit your needs for many types of vacations, at $956 per night.
$$$$
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
House
in Morris12 guests · 5 bedrooms · 5 baths
Pool · Pets allowed · Kitchen or Kitchenette
This attractive House in Berkshires, $814 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Charming lakeside cottage and guest cottage with spectacular views
House
in Morris10 guests · 5 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
This House for $816 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Family Friendly Townhouse in the Heart of Jiminy Peak
House
in Hancock10 guests · 4 bedrooms · 4 baths
Ski in / Ski out · Pool · Kitchen or Kitchenette
This House for $927 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Amore Estate - beautiful room with many places to explore and relax in.
House
in Lenox16 guests · 6 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner
The best choice in Berkshires for House, for $982 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
5Bdrm/6Bath estate on Lenox - Stockbridge border, near BSO Tanglewood
House
in Lee20 guests · 5 bedrooms · 6 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at 5Bdrm/6Bath estate on Lenox - Stockbridge border, near BSO Tanglewood, our elegant House in Berkshires. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Historic Stockbridge Villa on 25 acres sleeps 23
House
in Stockbridge23 guests · 11 bedrooms · 7 baths
Garden · Pool · Kitchen or Kitchenette
Experience the best of Berkshires with this House available for $911. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
House
in Sharon9 guests · 4 bedrooms · 4 baths
Garden · Pool · Pets allowed
Are you ready to indulge in a relaxing getaway? Our House in Berkshires has everything you need for a rejuvenating stay. Treat yourself to Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Wellspring by AvantStay | Indoor Pool + Views
House
in West Stockbridge12 guests · 7 bedrooms · 5 baths
Pool · Kitchen or Kitchenette · Air conditioner
This House for $1,059 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Best Town WASHINGTON! PoshPadsCT"51 SENFF" 2Hrs-NYC Mint 5BR, Ski, BBQ, HotTub!
House
in Washington12 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
This attractive House in Berkshires, $967 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
Farm Stay
in New Marlborough11 guests · 5 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
Nestled in Berkshires, this Farm Stay is perfect for your next vacation. Enjoy 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Cabin
in Austerlitz12 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Berkshires, at $833 per night for your next great vacation.
$$$$
Start earning One Key rewards
Dream getaway - mtn views, ski, pool, BBQ, Firepit, Kid friendly, Lakes, WFH
House
in East Chatham12 guests · 6 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
The best choice in Berkshires for House, for $867 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Forget-Me-Not by AvantStay | Bold Lakefront Escape
House
in Monterey12 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
This House in Berkshires, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
House
in Monterey14 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
This attractive House in Berkshires, $806 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Berkshires travel inspiration
Read our blogGuides
7 Best New England Towns for Fall Foliage
Budget Travel
Best Staycation Cities in the United States: 50 States Edition
Keep exploring
- Kauai Villas
- Orlando Villas
- Kiawah Island Villas
- Miami Beach Villas
- Kissimmee Villas
- North Naples Villas
- Florida Keys Villas
- Phoenix Villas
- Los Angeles Villas
- St Petersburg Villas
- Palm Desert Villas
- Miami Villas
- Las Vegas Villas
- Venice Villas
- Key West Villas
- Palm Springs Villas
- Lake Tahoe Villas
- Hollywood Hills Villas
- Seabrook Island Villas
- South Lake Tahoe Villas
- Pocono Mountains Villas
- Scottsdale Villas
- Myrtle Beach Villas
- Hilton Head Island Villas
- Marco Island Villas
- North Miami Villas
- Sanibel Island Villas
- West Palm Beach Villas
- Fort Myers Beach Villas
- Haines City Villas
- North Las Vegas Villas
- Destin Villas
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals