Peaceful Woodland Home in the Heart of the Berkshires
House in Stockbridge, MA
8 guests · 4 bedrooms · 2 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
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.
The house gets beautiful sunlight and has a fireplace and a deck overlooking the woods. The property includes a separate ping pong room that owners may access. Interested guests may inquire about use of the “The Office”, a studio space that can be used for writing, art, or meditation; with prior notice, this space can usually be made available as well.
The house is conveniently located near many of the area's attractions, including the shops and restaurants of Great Barrington and Lenox, Stockbridge’s famous Red Lion Inn, and Tanglewood, the summer home of the Boston Symphony Orchestra. The Chesterwood museum and gardens are only a half mile down the road, and the Norman Rockwell museum just slightly further. For those who want to swim, the Stockbridge Town Beach and the Stockbridge Bowl are a short drive away. Winter guests may want to visit nearby Butternut Ski Resort - or just stay on the property and sled down the driveway.
The rental apartment adjoins the caretaker's apartment (it shares a wall, but has a separate entrance.) As mentioned above, guests may also access the ping pong room and, with prior arrangement, the Office, and are encouraged to explore the extensive grounds.
There is a washer and dryer in the unit for your use.
Each of the bedrooms were recently upgraded with new mattresses.
The house gets beautiful sunlight and has a fireplace and a deck overlooking the woods. The property includes a separate ping pong room that owners may access. Interested guests may inquire about use of the “The Office”, a studio space that can be used for writing, art, or meditation; with prior notice, this space can usually be made available as well.
The house is conveniently located near many of the area's attractions, including the shops and restaurants of Great Barrington and Lenox, Stockbridge’s famous Red Lion Inn, and Tanglewood, the summer home of the Boston Symphony Orchestra. The Chesterwood museum and gardens are only a half mile down the road, and the Norman Rockwell museum just slightly further. For those who want to swim, the Stockbridge Town Beach and the Stockbridge Bowl are a short drive away. Winter guests may want to visit nearby Butternut Ski Resort - or just stay on the property and sled down the driveway.
The rental apartment adjoins the caretaker's apartment (it shares a wall, but has a separate entrance.) As mentioned above, guests may also access the ping pong room and, with prior arrangement, the Office, and are encouraged to explore the extensive grounds.
There is a washer and dryer in the unit for your use.
Each of the bedrooms were recently upgraded with new mattresses.
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Stockbridge, MA
$$$$
Reviews
10.0
A little piece of paradise. Stunning setting and very comfortable accommodation. Love breakfast on the deck/porch. Perfect for Tanglewood and environs. Donna, our host was very helpful. Only thing missing were a few kitchen tools (vegetable peeler and colander. Hope to return next year. Donna, thank you for sharing your family’s wonderful home!
10.0
The Residence was the perfect Basecamp for our long weekend in the Berkshires. It had a mix of amenities that suited everyone in the family. The possibility of first floor living was a plus for my senior dog and I and the two spacious bedrooms upstairs worked well for the rest of the family. We visited to experience Stockbridge Christmas and the holiday events connected to the Main Street recreation. The weather was horrible on one of the days but coming back to the Residence and being able to dry our soaked winter gear in the dryer and light a fire using provided firewood was amazing. The home is only about 6-10 minutes away from many attractions including Main Street Stockbridge, the Norman Rockwell Museum, the Mount, and Naumkeag. If it wasn’t winter we would have loved to visit Chesterwood, a 5 minute walk up the road. Donna was very accommodating. She left us a loaf of bakery bread in the freezer, baggies for the dog, and allowed us to check in early (amazing since the road might have been challenging to navigate in the dark the first time around). Thanks for a wonderful stay.
10.0
We enjoyed our stay very much. The surrounding woods are very soothing and quiet. The house was comfortable for 3 older adults.
10.0
The house and property made for a quiet and relaxing setting for myself and two friends. We thoroughly enjoyed morning runs on country roads and coffee on the deck listening to the birds. The house was very clean and cozy with a well stocked kitchen for cooking. Donna is a gracious and considerate host and readily answered all our questions about the property, restaurants and suggestions on things to do. I only wish we had more time to see it all!
10.0
Comfortable and spacious inside and out. Lots of history and we’ll lived in feel. Host very responsive. Well equipped and close to Tanglewood. The weather was very hot and the AC was adequate but not great.
10.0
We had a lovely stay while visiting Tanglewood. Donna was a lovely, thoughtful host during our stay. The property is beautiful and incredibly convenient to Tanglewood, Stockbridge, Lenox, and all the local sites. The house was well stocked and even thoughtfully had items for a infant/toddler (play pen, high chair, etc). I would definitely recommend staying here!
10.0
Our group of 2 couples enjoyed our stay on this woodsy property. Linda, the innkeeper, was exceptional. She allowed an early check-in, set up a hammock, left a delicious bread, and provided a rain shelter for Tanglewood. The house was clean and comfortable. It was fun to stay at the home of one of Tanglewood’s founders and original ticket office. We easily walked to Chesterwood and had access to Stockbridge and all of the Berkshire attractions. For those of a certain age, the vintage kitchen and bathrooms were reminiscent of bygone years. Thank you for sharing this special property.
10.0
We traveled with 4 adults, 2 kids under age 5, and a dog, and the house was perfect for us! The kitchen was well-equipped and Donna provided a high chair for our 2-year old. The bedrooms were comfortable and all linens and towels were provided. The kids loved exploring the property and playing near the stream. Highly recommended!
10.0
Emma and Donna ensured we had a truly lovely time at The Residence. We felt so welcomed, and the property had everything we needed, from a kitchen stocked with appliances to the prepped fireplace and materials. The property itself is so blissfully quiet, and was perfect for us and our dogs to wander the grounds. Close enough to Stockbridge and Great Barrington to ski or eat, this place was a great fit for a chill weekend. Donna was so responsive when we had questions, and they were so accommodating when we needed to leave a day early. The place was way too big for one couple and their dogs, but the price and location made it a steal!
10.0
We met friends from Boston for a family friendly ski weekend at butternut. The house was perfect for our needs. We enjoyed cooking our dinners in, and the fireplace in the evening. Hosts were very accommodating, providing a pack and play and high chair for the infant in our group, and letting us check out late to enable a morning of skiing Monday. Thank you!
10.0
Great location and house. Thourghly enjoyed the time their
10.0
Very enjoyable. Cute that Donna had a little tricycle ready for our grandson
10.0
Lovely quiet and beautiful property. We all loved it…especially the dog!
10.0
Tucked away house in the woods ! A great escape from our busy urban lifestyle. Lots of trees, next to Chesterwood, and near hiking trails .
10.0
We had a great time. Donna was great.
10.0
We spent a peaceful four days in the cottage tucked away in the hills of West Stockbridge. Despite 95deg temps in town the surrounding trees and the house itself kept the heat off. There are window AC’s but we never needed them.
This is a good choice for a couple or small family that is looking to unplug and enjoy each other. Cell service is minimal and the WiFi won’t keep gamers happy, but it was ok for us. Enjoy the environs, but don’t miss the eclectic collection of books in the foyer.
10.0
Wonderful home in a gorgeous setting
This comfortable home was just right for our group of 6: 2 adult couples and 2 teenagers. The woodsy setting offers plenty of outdoor space to enjoy and is convenient to downtown Stockbridge, Great Barrington and local cultural attractions. We would love to return!
10.0
A Peaceful Wooded Retreat
This property delivered on all it promised. Deeply wooded but very close in to Housatonic, Stockbridge and Great Barrington. Donna, the property manager, was very helpful in getting us settled and answering a few questions. The kitchen is well supplied even for a larger group. All the rooms were spacious and comfortable. Many reading areas. The hammock in the yard is the most comfortable I have ever enjoyed. We loved coffee and cocktails on the deck, though the deck could use a refreshing power wash and refresh stain. The view is instant relaxation. There are some short lovely trails on the property. Would be helpful if each was marked. We lost two of the trails several times. I would look forward to more visits. Autumn will be beautiful. The cozy fireplace begs for winter's evening rest.
If you love bird songs, sunlight through trees and hours of peaceful solitude this is the residence for you.
10.0
Great Place!
We have zero complaints, the place was great
10.0
Wonderful Stay
What a great place to stay! The house is set in the woods and has so many hiking trails and a babbling brook. Inside was sparkling clean and very comfortable. We enjoyed the bread and syrup that was left. The ping pong room was fun as well. We had a couple questions and Chris responded immediately. We would definitely come back here!
10.0
Get away
Quiet secluded cabin in the woods. Exactly what we were looking for. Great hosts, great location, clean rustic and comfortable
10.0
Berkshire Winter getaway
My family had a great time staying here. Chris and Emma were very responsive and helpful. We loved exploring the property and having roaring fires every night. The location couldn't be better for exploring everything the Berkshires have to offer. We will definitely be back!
10.0
Winter Escape
We had a great stay for 2 nights at this house on large property. I booked this house hoping to ski, but also knowing that if we couldn’t ski we could do some hiking. The location was 15 minutes to butternut and 45 minutes to Jiminy peak. While my kids and husband skied, I took my dogs hiking at Monument Mountain. The caretakers were at the attached house while we were there, but that was fine. There was plenty of room at the rental, including a fireplace that warmed us up. Check in and out was easy. We hit Taft’s farm for Cider donuts, muffins and zucchini bread. All their recommendations were perfect. I would definitely stay again and would also consider staying when weather was warmer for more hikes.
10.0
Peaceful wooded getaway
Great little place on a unique property. Tons of trails to walk right outside the door. Very quiet and peaceful, nice place to relax. Third bedroom is small with only a full bed, so best for a kid. Properties are older but kept up, air conditioners in every room and the fireplace works which was a treat on a rainy day. Caretakers on site if you need anything. 10 minutes to Stockbridge, 2 minutes to Rockwell Museum, walkable to the river.
8.0
great stay
The property is very comfortable. It is a little difficult to find after dark the first time. Great 3 bedrooms! The pullout couch in the 3rd is not very comfortable for an adult of 2. Great WiFi, terrible cell coverage. 15 minutes to downtown Lenox, passing Tanglewood. It was very humid so bedroom airconditioners were used. Kitchen was fine, fresh flowers and homemade cookies awaited us! SIMPLE check out process, we followed directions in book, but hope we did enough.....
6.0
Quaint country life.
The house is a great layout in a great location near Lenox, Stockbridge and Great Barrington. The owner is very nice and helpful. Unfortunately the house had some bad odors that never went away and some of the furniture needs to be replaced.
10.0
Woodsy Getaway
Place was great, it was cozy and comfortable as advertised. We took advantage of the fireplace and the wood provided. It has good access to the Berkshires. Close by is Monument mountain which has a long ridge on a couple mile hike so we got lots of good views. Also, we went to wine festival at Chatham fairgrounds which was not far. Last, we rented a pontoon boat on Lake Pontoosuc in Pittsfield for a couple hours. Next time around we'll visit the Stockbridge Bowl, drive up Mount Greylock, and go to the Norman Rockwell museum.
10.0
Wonderful, cozy and welcoming
Had a perfect snowy winter weekend. The house is perfect for cooking and hanging out by the fire. Would definitely go back!
10.0
Great home in the woods, near Butternut skiing
Very nice home. Beautiful property with a brook that runs through it. We split with two families (w/ kids), and everyone was comfortable and cozy. We built a fire in the fireplace all three nights. Well equipped kitchen. Cable TV. Short, 15-minute drive to Butternut Mountain.
10.0
Great weekend get away with friends
What a gem! 4 adults and 4 kids were comfortable and cozy in this woodsy retreat in West Stockbridge. With temperatures in the double-digit negatives, we were not able to explore the property as much as we wanted but the hikes that we were able to take were breathtaking and the kids LOVED exploring the woods and the creek. The house was a perfect fit for our group, whether we were hanging out in front of the fire, or the kids were playing board games in "their" room upstairs, we were comfortable and happy. The property has this great feeling of being super remote and isolated but being really close to all the area attractions all at the same time. The owners were extremely helpful and responsive every step of the way.
10.0
A quiet, peaceful retreat but still conveniently located.
First off let me say that the owners are incredibly responsive to any question. We had a cable tv issue, which could only be resolved by the old unplug, plug back in method. It was also uncharacteristically hot for May and the room air conditioners as well as dehumidifier literally saved our vacation. The home is even more beautiful in person. We felt so relaxed there, that we decided to forgo our usual dinners out and eat-in. The cable stations are robust for we eat-in couch potatoes. I got to watch the French Open and professional golf, and the hubby watched his cycling shows on BEIN.
Some places I'd recommend for eating, Once Upon a Table in Stockbridge for lunch. There's a chocolate shop located behind them with great gelato for dessert. We got take-out from The Brick House Pub in Housatonic, very close-by which was always excellent. For breakfast we went to Haven Cafe and Bakery as well as Spoon in Lenox. Also Pleasant and Main Cafe in Great Barrington is a nice spot too.
If you have a dog, try Kennedy Park in Lenox. It's completely shaded and has short or long loops. And don't forget Taft Farm in Great Barrington for their fresh baked cookies and brownies.
10.0
Lovely peaceful getaway
My sister, cousin and I all want you to know how much we enjoyed your family home. With the exception of the saggy downstairs bed, (which has now been replaced!) everything was welcoming, comfortable and perfectly suited for our little gathering. We spent happy evenings before a crackling fire, sharing our stories, playing cards (have you ever tried Spite and Malice?) and making simple meals. Spring was on the verge of bursting forth. As a Californian, the abundance of water was a welcome novelty and I have a great appreciation for the boulders and stone walls that are found everywhere. So thank you for sharing your home with us.
8.0
Peaceful getaway
Very Peaceful spot for a family getaway. Lovely property, nicely equipped kitchen. Clean house. The bedroom downstairs needs a new mattress, but the other two were OK. THe fireplace was great and lots of firewood on hand. All in all was a wonderful place to spend the Christmas holiday.Beautiful, quaint town. Wish there was snow! Like many country homes, it does have mice! We heard them in the walls at night and found a dead one in a trap in the kitchen. Given the location, not surprising. Nice hiking trails on the property.
10.0
Beautiful property, peaceful and serene
The property is beautiful and very secluded/surrounded by lots of trees. The emphasis on preserving nature in the area and especially on the property makes it very peaceful and private. We had a lovely weekend in the cottage, and with Lenox and Great Barrington very close, there is certainly lots to do and see. Monument Mountain also very close and provides wonderful hiking and stunning views, not to mention grounds around the property itself also include lovely forested trail and a nearby pond. The cottage was very clean and comfortable, and provided for all of our needs. Perfect for a weekend getaway.
10.0
Wonderful spot
Our group of college friends needed a place for a weekend wedding in the Berkshires and were very pleased with our stay at the Residence. Comfortable, charming, quiet and easy access to Lenox, Stockbridge, Great Barrington and the rest. Highly recommend the house and the managers were super easy to deal with during the booking process.
10.0
Family retreat in the Berkshires
We really enjoyed this charming old house in the deep woods of the Berkshires. We arrived late on a Friday night and Michael had a fire ready to be lit, so cozy and warm. The place was clean and comfortable with an ideal location to hiking and cute little New England towns. Of course the leaves were just beautiful. Ate at the Prairie Whale in Great Barrington and it was excellent, also the brewery had good food. I would recommend this property, it was great!
10.0
comfortable home in a beautiful setting
My brother, sister-in-law, dog and I came up for a weekend of downhill skiing at Butternut (in Great Barrington), and snowshoeing in Kennedy Park (in Lenox). This house was perfectly situated to both locations, and gave us a warm, comfortable home base in which to relax after our outings. Though central to these surrounding towns, it has the feeling of remoteness due to the amount of land and way it is tucked away in the woods. We found the house roomy, warm and well furnished, with comfortable beds and a nice eat-in kitchen. There is a magnificent fireplace which we used every night, with plenty of firewood and kindling available. Due to the snow cover, it was impossible for us to explore the grounds very much, but it looks to be a lovely place to come in the summer for hiking, etc. Thanks very much to the owners for allowing us the use of their lovely home! Hope to be back one day. :)
8.0
Charming house, beautiful setting
We stayed at this lovely cottage with our two young children and had a wonderful time. The setting is magical - wooded with some really fun sledding hills. There is an unheated recreation cabin with ping pong that would be terrific in summer but was a bit too cold in February. The house itself is very nice with three bedrooms and an eat-in kitchen that is open to the small living area (that has a magnificent fireplace and firewood is included). The rental unit is actually part of a house that is also occupied by the caretakers, a nice young couple. The rental part is completely separate from the caretaker's space. This, however, is not what we expected (I thought they would be in a different building) and the close quarters meant that we heard the thumping base of the music they played on their stereo. Not terrible, but since we live in an apartment where we hear our neighbors all the time it was a disappointment to be in such close quarters with other people.
10.0
perfect peaceful retreat
just had a perfectly relaxing girls weekend at the house and we were thrilled. the house is close to town but on so much land we had the best of both worlds. the house is very well kept and so cozy and inviting. the beds were very comfortable. we spent hours hiking the trails in the woods on the property and sitting in front of the fireplace. there is loads of firewood for renters use. we are planning a return in the fall. dont miss dinner at the red lion inn and a visit to the norman rockwell museum.
8.0
Quiet and cozy - Perfect for a relaxing getaway
This property was exactly what we needed for a relaxing and quiet getaway weekend. The owners were extremely helpful when we were booking, the place was clean and inviting when we arrived and surrounding attractions were great for the fall foliage and enjoying the outdoors. Nothing like a warm fire and good night sleep to take your mind off the stresses of working life. Monument Mountain was a very close and convenient hiking location to enjoy the fall foliage. I would definitely recommend this place if you are looking for a romantic getaway weekend or just a place to escape with a couple friends.
FAQs
How much does this house cost compared to others in Stockbridge?
The average price for a rental in Stockbridge is $330 per night. This rental is $11 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Peaceful Woodland Home in the Heart of the Berkshires. 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 Peaceful Woodland Home in the Heart of the Berkshires 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 Peaceful Woodland Home in the Heart of the Berkshires?
We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.
Explore similar vacation rentals in Stockbridge
Explore all rentals in Stockbridge
Stockbridge Country Inn
Bed and Breakfast
in Stockbridge1 king bed
Garden · Pool · Kitchen or Kitchenette
This Bed and Breakfast in Stockbridge, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
The Red Lion Inn
Hotel
in Stockbridge3-star
1 king bed
Garden · Pool · Air conditioner
Looking to create some memories in Stockbridge? Look no further than our Hotel, The Red Lion Inn. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
The Red Lion Inn
Hotel
in Stockbridge3-star
2 guests · 1 bedroom · 1 bath
Garden · Pool · Air conditioner
This Hotel in Stockbridge, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
House
in Stockbridge8 guests · 5 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Experience the best of Stockbridge with this House available for $476. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
A Grand property in Historic Stockbridge
House
in Stockbridge12 guests · 6 bedrooms · 8 baths
Garden · Kitchen or Kitchenette · Air conditioner
This attractive House in Stockbridge, $1,297 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
The Red Lion Inn
Hotel
in Stockbridge4-star
1 queen bed
Pool · Pets allowed · Internet / Wifi
Enjoy the best of Stockbridge in our Hotel, The Red Lion Inn. A stunning property with amenities including Fireplace, Internet / Wifi and Pets allowed, and more.
$$$$
Start earning One Key rewards
Modern Cottage in the heart of the Berkshires with new exterior flex space!
House
in Stockbridge8 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed
When traveling to Stockbridge, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $503 per night.
$$$$
Lovely Berkshire Home 1/10 mile from Town on 11 acres
House
in Stockbridge8 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Are you ready to indulge in a relaxing getaway? Our House in Stockbridge has everything you need for a rejuvenating stay. Treat yourself to Lovely Berkshire Home 1/10 mile from Town on 11 acres's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Classic Stockbridge Cottage
House
in StockbridgeGarden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Stockbridge at Classic Stockbridge Cottage for $70 for your next trip.
$$$$
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing
House
in Stockbridge24 guests · 12 bedrooms · 8 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing, our elegant House in Stockbridge. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
House
in Stockbridge8 guests · 4 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
When traveling to Stockbridge, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $729 per night.
$$$$
The Inn at Stockbridge
Bed and Breakfast
in Lee1 king bed
Garden · Pool · Kitchen or Kitchenette
Top rated
The best choice in Stockbridge for Bed and Breakfast, for $286 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
The Inn at Stockbridge
Bed and Breakfast
in Lee2 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen or Kitchenette
Indulge in a peaceful retreat at The Inn at Stockbridge, our elegant Bed and Breakfast in Stockbridge. Enjoy amenities including Air conditioner, Internet / Wifi and Balcony or Patio, and more.
$$$$
Too Good AKA 2 Goodrich St
House
in StockbridgeGarden · Kitchen or Kitchenette · Air conditioner
Experience the best of Stockbridge with this House available for $73. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Secluded Family Home in Serene Stockbridge Woods
House
in Stockbridge8 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
This House in Stockbridge, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Historic Stockbridge Villa on 25 acres sleeps 23
House
in Stockbridge23 guests · 11 bedrooms · 7 baths
Garden · Pool · Kitchen or Kitchenette
Experience the best of Stockbridge with this House available for $911. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
1 Mi to Dtwn Cottage with Large Yard in Stockbridge
House
in StockbridgePets allowed · Kitchen or Kitchenette · Air conditioner
This inviting House in Stockbridge can fit your needs for many types of vacations, at $73 per night.
$$$$
Classic Stockbridge Cottage
House
in Stockbridge8 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a memorable stay in Stockbridge? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Find your Sanctuary at The Rectory at Stockbridge
House
in Stockbridge12 guests · 5 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
This attractive House in Stockbridge, $1,072 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Woodland Zen by AvantStay Modern Design Patio
House
in StockbridgeKitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for a memorable stay in Stockbridge? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Modern Cabin Near Tanglewood
Cabin
in West Stockbridge9 guests · 4 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Are you ready to indulge in a relaxing getaway? Our Cabin in Stockbridge has everything you need for a rejuvenating stay. Treat yourself to Modern Cabin Near Tanglewood 's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Bed and Breakfast
in Stockbridge1 queen bed
Garden · Pool · Kitchen or Kitchenette
Top rated
Business stays, family stays, couples stay, getaway vacation, and rental in Stockbridge at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood for $513 for your next trip.
$$$$
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Bed and Breakfast
in Stockbridge2 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen or Kitchenette
Enjoy the best of Stockbridge in our Bed and Breakfast, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood. A stunning property with amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
Wellspring by AvantStay | Indoor Pool + Views
House
in West Stockbridge12 guests · 7 bedrooms · 5 baths
Pool · Kitchen or Kitchenette · Air conditioner
This House for $1,228 in Stockbridge, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Wellspring by AvantStay Indoor Pool Views
House
in RichmondPool · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Stockbridge, at $103 per night for your next great vacation.
$$$$
New to VacationRenter
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Farm Stay
in Stockbridge10 guests · 5 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Enjoy the best of Stockbridge in our Farm Stay, New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Woodland Zen by AvantStay | Modern Design + Patio
House
in Stockbridge8 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Stockbridge in our House, Woodland Zen by AvantStay | Modern Design + Patio. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Stockbridge Retreat with Pool and Hot Tub!
House
in StockbridgeGarden · Pool · Kitchen or Kitchenette
Looking for a House in Stockbridge, this House for $73 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Stockbridge Estate with Mountain Views
House
in Stockbridge8 guests · 4 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
Are you ready to indulge in a relaxing getaway? Our House in Stockbridge has everything you need for a rejuvenating stay. Treat yourself to Stockbridge Estate with Mountain Views's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Start earning One Key rewards
Gracious Berkshire Retreat
House
in Stockbridge10 guests · 3 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Discover the beauty of Stockbridge with a stay at Gracious Berkshire Retreat, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Stockbridge travel inspiration
Read our blogGuides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
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