Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
Cottage in Bearsville, NY
4 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valuePrice for this property is higher than average in the area
About this cottage rental
The Bearsville Retreat is a secluded bucolic compound nestled in the trees of Bearsville, a quarter mile from the gourmet marketplace The Cub and the historic Bearsville Theater, and just two miles (5 min drive) to Woodstock's town center. The property consists of two charming cottages, freestanding office, heated saltwater pool (there is an additional fee to heat the pool), luxurious hot tub, fire pit, and a children's play structure. Pastoral and mountain views abound. Come relax, recharge, and enjoy the natural beauty of the Catskills.
Located in Bearsville, a hamlet of Woodstock, the serene two-acre property is tucked away from the road, with beautiful mountain views, providing a postcard-perfect backdrop to wake up to every morning, while also close to everything. Spend your afternoons swimming in the heated saltwater pool, relax in the hot tub, or lounge in a hammock in the apple orchard while the kids swing and play in the club house. Pass your evenings barbecuing and dining alfresco on the bluestone patio, playing charades in the game room, or roasting marshmallows in the fire pit. Located within the historic township of Woodstock, with it’s charming boutiques, farm-to-table restaurants, and rich history of music and art, The Bearsville Retreat is the perfect spot to enjoy all that the Catskills have to offer.
THE MAIN HOUSE has two bedrooms: The primary bedroom has a queen bed, and the second bedroom has two twin beds — both bedrooms are cozy and comfortable with designer furniture, premium bedding, and new skylights. The brand-new kitchen is fully stocked with microwave, coffee maker, and everything you need to cook for family or guests. The bathroom features both walk-in shower and deep soaking tub — a relaxing treat at the end of a long day of hiking or skiing. The stylishly-decorated living room has a wood burning fireplace and plenty of comfy seating, Apple TV, bluetooth stereo/record player, and wifi that extends across the property. The game room, which is stocked with board games, puzzles, art books and an antique chess/backgammon table, leads out to a sunny bluestone patio with a twelve-person al fresco dining table and barbecue. The wood-paneled dining room is a cozy space with the feel of an old fashioned captain's stateroom, an ideal spot for both quiet breakfasts and lively dinner parties.
THE GUEST HOUSE features open floor plan with a loft-like, sun-filled living room with a wall of windows facing onto the pool. There is wifi throughout the house, as well as a smart TV/Blue ray and record player. There is a mini library filled with books and DVDs which can be enjoyed on the sofa in front of the pot-bellied stove. The chef’s kitchen is fully equipped with new appliances, a marble-topped island, and plenty of counter space for preparing meals. The spacious dining area comfortably seats six. The bedroom has a luxurious king sized bed with upholstered headboard, and plenty of natural light from windows facing out to the pool. The bathroom features a deep soaking tub and skylight, perfect for relaxing and looking up at the stars. The sofa in the living room converts into a queen bed for extra sleeping space (please let us know ahead of time if you want this bed made up before you arrive).
THE GROUNDS' beautifully maintained sprawling lawns are picturesque. The 20' X 40' heated saltwater pool (additional heating fee), outdoor shower, and brand new hot tub are privately situated in the back yard, while the front yard features an apple orchard, pastural views of the historic neighboring farm, a fire pit, and a 'Brad's Barns Expedition' children's swing-set, with play structure, and club house.
THE OFFICE is a freestanding building located behind the main house. It is equipped with a desk, plush couch, and hardwired ethernet. It is private and comfortable, making work away from home a breeze.
See you soon!
Located in Bearsville, a hamlet of Woodstock, the serene two-acre property is tucked away from the road, with beautiful mountain views, providing a postcard-perfect backdrop to wake up to every morning, while also close to everything. Spend your afternoons swimming in the heated saltwater pool, relax in the hot tub, or lounge in a hammock in the apple orchard while the kids swing and play in the club house. Pass your evenings barbecuing and dining alfresco on the bluestone patio, playing charades in the game room, or roasting marshmallows in the fire pit. Located within the historic township of Woodstock, with it’s charming boutiques, farm-to-table restaurants, and rich history of music and art, The Bearsville Retreat is the perfect spot to enjoy all that the Catskills have to offer.
THE MAIN HOUSE has two bedrooms: The primary bedroom has a queen bed, and the second bedroom has two twin beds — both bedrooms are cozy and comfortable with designer furniture, premium bedding, and new skylights. The brand-new kitchen is fully stocked with microwave, coffee maker, and everything you need to cook for family or guests. The bathroom features both walk-in shower and deep soaking tub — a relaxing treat at the end of a long day of hiking or skiing. The stylishly-decorated living room has a wood burning fireplace and plenty of comfy seating, Apple TV, bluetooth stereo/record player, and wifi that extends across the property. The game room, which is stocked with board games, puzzles, art books and an antique chess/backgammon table, leads out to a sunny bluestone patio with a twelve-person al fresco dining table and barbecue. The wood-paneled dining room is a cozy space with the feel of an old fashioned captain's stateroom, an ideal spot for both quiet breakfasts and lively dinner parties.
THE GUEST HOUSE features open floor plan with a loft-like, sun-filled living room with a wall of windows facing onto the pool. There is wifi throughout the house, as well as a smart TV/Blue ray and record player. There is a mini library filled with books and DVDs which can be enjoyed on the sofa in front of the pot-bellied stove. The chef’s kitchen is fully equipped with new appliances, a marble-topped island, and plenty of counter space for preparing meals. The spacious dining area comfortably seats six. The bedroom has a luxurious king sized bed with upholstered headboard, and plenty of natural light from windows facing out to the pool. The bathroom features a deep soaking tub and skylight, perfect for relaxing and looking up at the stars. The sofa in the living room converts into a queen bed for extra sleeping space (please let us know ahead of time if you want this bed made up before you arrive).
THE GROUNDS' beautifully maintained sprawling lawns are picturesque. The 20' X 40' heated saltwater pool (additional heating fee), outdoor shower, and brand new hot tub are privately situated in the back yard, while the front yard features an apple orchard, pastural views of the historic neighboring farm, a fire pit, and a 'Brad's Barns Expedition' children's swing-set, with play structure, and club house.
THE OFFICE is a freestanding building located behind the main house. It is equipped with a desk, plush couch, and hardwired ethernet. It is private and comfortable, making work away from home a breeze.
See you soon!
Amenities
Pool
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Garden
Family friendly
Map of Bearsville, NY
££££
Ratings and reviews
5.0 / 5.0
Clean, comfortable, & well appointed space for our Woodstock weekend! Loved it!
5.0 / 5.0
The Bearsville retreat was amazing. Its location was perfect, the accommodations were spotless and the owner was super helpful and responded quickly. We left today and already rebooked for next year.
5.0 / 5.0
Lovely property
5.0 / 5.0
We loved these cottages! We were a group of 5 with kids, parent, and grandparents. The two-cottage set up was a great arrangement for us, giving the grandparents some privacy, and the pool and hot tub provided lots of entertainment for the kids.
The houses were well appointed with lovely furnishings and plenty of supplies/equipment for cooking and towels for the pool.
Location was another of our favorite features- the houses were on a beautiful piece of land beside a small farm, and just a five or so minute drive from the main part of Woodstock.
The one suggestion for improvement would be to some of the outdoor areas and furniture, which could use a power wash or, in some cases, to be replaced. Some shrubs could use cutting back, like at the end of the driveway and in the pool area, but obviously it’s tough to maintain such an extensive property!
We would absolutely stay here again.
5.0 / 5.0
My group and I had such a fantastic stay! The two cottages were comfortable and cozy and the pool was beautiful. We were close to town and other amenities. I would highly recommend a stay here, my group hopes to come back soon!
5.0 / 5.0
We really enjoyed our stay at the cottages. The setup was great for two families as we each had our own cottage, so privacy when we needed it but also great communal areas to come together for meals and fun.
We have two young kids, age 2 and 4 and they loved the playground area and seeing the deer and chipmunks around the property.
The pool was a really good size and temperature. Wish we could have used it more but some wasps decided to build their nest on the back of one of the loungers! Erica was really responsive about it and did her best to rectify the issue quickly.
The place is very convenient for exploring Woodstock and Bearsville and we had everything we needed for a relaxing stay, would definitely go back. Thanks Erica!
5.0 / 5.0
House was amazing and it was so easy and organized. We will be back!
5.0 / 5.0
It rained most for most of our stay, so it was quite cozy staying indoors. The fireplace and turntable were a plus!
5.0 / 5.0
I stayed for a month using both houses. The property is well equipped in a lovely setting with a fantastic pool. The manager responded quickly during normal hours. Great all around.
5.0 / 5.0
We absolutely loved our stay here, not only was it beautiful but it was so cozy. Town was extremely close by, as well as hiking and other acgivities. There was wildlife all around, beautiful deer to view on the lawn every morning and afternoon, and the view of the pool in the afternoon is a bird watchers dream. It felt like complete country living. We wished we had stayed longer! Our pup also enjoyed himself to the absolute fullest, having a fenced in yard was so amazing for him, he was able to run his heart out and we never had to worry! I was so pleased to be able to reach out whenever we needed something and got an answer right away from the property manager. We hope to stay here again!
5.0 / 5.0
We came for a long weekend (2 couples). The main house has two beds, very comfortable for the four of us. The guest house which we didn’t need to use would have been great for another couple or even a family. Plenty of space all around. The fireplace was great and stocked with plenty of wood.
To start, Sarah was extremely responsive and accommodating with us regarding checkin and out time. She has a very detailed list of things to do around the area and a house manual. Some reviews noted a bunch of “rules”, but all seemed totally reasonable to us and we found the information very helpful.
The house had a hot tub which we used and a beautiful pool which we did not given it was October. I could see spending a ton of time in the pool in spring/summer - it was really nice.
The house was close to the town so getting meals was easy. Also the house is close to Overlook Mountain (and others) and we went on a nice hike (about 4 hours round trip).
Overall, it was a fantastic weekend getaway and we hope to come back soon.
4.0 / 5.0
Our family very much enjoyed our stay at this property. It was peaceful and tucked away. However, I was overwhelmed with the amount of communication that the owner wanted, and with the threat of extra charges in how the property was used. We ended up using the property far less than I had originally anticipated due to the extensive rule book and list of activities that would incur further charges. Furthermore, the description that the pool was heated was inaccurate and should have read that the pool ‘has the ability to be heated at great additional cost’. While we made a fun week of it, this was by far the most stressful booking I’ve ever had through VRBO, and I had the impression that the owner wasn’t actually interested in this being used as a rental property.
4.0 / 5.0
Our vacation started out stressful as our dog ingested poison from a rodent trap. We had to go to an all night vet and were up most of the night. Our dog is fine thank goodness! The home owner was really helpful. One the phone with us in the middle of the night, helping with the vet and vet bills. I could tell she really cared and did all she could for us. I could not have asked for her to be more ready to help us in any way.
She has made a beautiful, peaceful place. Everything you need is in the kitchen, including high quality knives, which I always appreciate. The property is quiet and private. The views across the farm are beautiful. She has a house book with a lot of instructions, which helps with answering most of your questions but she is very available if questions come up. There are quite a few house rules, but that is how she keeps the house so nice. She also has great suggestions in the book for local activities and restaurants, some you would not find in a guide book. All and all, a thoughtfully run place.
I would suggest two things. I wished there was more light at night. The light bulbs are low wattage and I would have wanted it brighter. I would also suggest a large bread box to put food that really shouldn't go into the fridge as she wants no food left out.
So, you would think that after the scare with our beloved family member we would have left with a bad feeling, but we did not. Sarah was great and so was her place. I would recommend it to my friends and would return myself.
5.0 / 5.0
Close to town and the Cub Market, private, quiet
5.0 / 5.0
The property was perfect for a quick little getaway. Can’t wait to book it again. :)
5.0 / 5.0
Perfect little getaway with the wife and kids. Property is beautiful and peaceful just a great experience from booking to check out!!
5.0 / 5.0
We cant say enough nice things about this property. Started off with very easy and informative communication with the owner. The property itself checks all the boxes for a wonderful weekend away, especially for those with dogs. The entire property is completely fenced so the dogs could roam free without a worry.
We weren't able to use the pool as it was April, but the hot tub was lovely. We also used the grill quite a bit to cook very easily.
The houses are updated in the most important places, kitchen and bathroom. While the rest of the house has such charm and character. The open windows make the space relaxing and inviting. We had a fire inside every night while enjoying a night cap and chat.
The location is extremely convenient to nearby shops, restaurants of Woodstock and Bearsville.
We wish we would have stayed longer, so we will be back, as long as we can get a booking.
Thanks again Sarah.
5.0 / 5.0
I enjoyed my time at Sara’s property, conveniently located about 4 minutes drive, from Woodstock. The space was clean, beautifully decorated and comfortable. Looking forward to booking again!
5.0 / 5.0
This property has lots of charm and a great location too. Looking out the large picture window onto the snow-capped mature trees by the cozy fire was a real treat. Clean and comfortable it has all you need for a great time away. Sarah was an incredible host and went above and beyond!
5.0 / 5.0
Our group had a great weekend stay at the Bearsville Retreat. The property itself is beautiful/perfectly located and the main house and guest house are both well appointed and stocked with everything you need to enjoy your time. Highly recommend and would definitely book again. Thanks!
2.5 / 5.0
What a lovely place for a winter vacation. Hot tubbing in the snow? Check! Amazingly comfy master bed, too.
2.5 / 5.0
This was a perfect little getaway for us. Exceptionally clean, thoughtfully prepared. Functional kitchen, nice bedrooms. The property is beautiful and has a lovely farm next door, contributing to the peaceful view. Very close to Woodstock. Highly recommend!
2.5 / 5.0
This property is a lovely gem in the quiet woods. Long driveway takes you to a large yard. My dog enjoyed playing fetch in the snow. Close proximity to town for shopping. Hiking trails nearby for more scenery and exercise. Beds were very comfortable. All we needed for a weekend away!
2.5 / 5.0
We loved our time in Bearsville! The houses had everything we needed and we were able to watch the snow from the huge windows while staying cozy inside. The hot tub was a great ending to our days. Thanks so much for a great stay!!
2.5 / 5.0
A beautiful weekend retreat! We really enjoyed our stay at this pretty, quiet, well maintained, cozy cottage in Bearsville , just down the road from Woodstock.. It’s nestled off the road surrounded by woods and a orchard, next to a lovely farm , with lots of outdoor fun and culture in the local Woodstock area .
2.5 / 5.0
Absolutely enjoyed my stay —pure relaxation and comfort. The place and property were beautiful; it was serene. The guest and main house were amazing to stay in and provided the best place to stay for a small group. The Reynolds’s farm next door just added to the charm of everything. The ability to have a fire left everyone cozy and at peace. Loved my stay and would recommend to anyone. The perfect place for a vacation.
2.5 / 5.0
A beautiful property in a beautiful setting. So much to do in the surrounding area of Woodstock.
2.5 / 5.0
We wanted the chance to relax in different surroundings (surprising how working from home for most of the year can make you stir crazy!) and get our Christmas season off to a good start, and boy did the house fit the bill. We stayed in the main house at Bearsville and it is wonderful; cozy, clean and fully stocked. We loved the curtained in main bedroom - a modern twist on a four poster. And the Christmas lights round the fireplace were a delightful touch. The location is also great - just a few minutes drive into town for shopping and eating. All in all a wonderful retreat and perfect place to recharge. Oh, and the dog loved it too!Thank you!!
2.5 / 5.0
Had a great time tucked away in the snow with a couple of friends and dog. The house was amazingly clean and Sarah could have not been more helpful. Big plus is how comfortable the beds were. We will be back in the summer.
2.5 / 5.0
My friends, dog, and I had a wonderful fall vacation at The Bearsville Estate. The houses are so cozy and charming, while beautiful large picture windows and numerous skylights made us feel like we were always connected to the nature. The main house bathroom with a high ceiling and a deep tub is a dream!! My dog loved exploring the all-fenced land. This place feels secluded and tranquil, while bing so close to Woodstock. Sarah was very communicative and helpful, making sure we are having a good time. Cannot wait to come back during the pool season next!
FAQs
How much does this cottage cost compared to others in Bearsville?
The average price for a rental in Bearsville is £205 per night. This rental is £155 above the average.
Is parking included with this cottage?
Yes, parking is listed as an amenity at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cottage?
Yes, a swimming pool is available for use at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.. Enjoy the water!
Is Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. pet friendly?
Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.?
We found 14 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.
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