Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

Photo gallery for Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

Pool amidst the natural beauty
Sprawling front lawn looking towards main house
Pastural front lawn with apple orchard
Main house
Beautiful vistas from both cottages

Overview of Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

Reviews
10 out of 10 Exceptional

Popular amenities

  • PoolPoolPool
  • Pet-friendlyPet-friendlyPet-friendly
  • Hot tubHot tubHot tub
  • KitchenKitchenKitchen
  • Free WiFiFree WiFiFree WiFi
  • Air conditioningAir conditioningAir conditioning

Check out the area

Map
Bearsville, NY
  • Popular LocationWoodstock Public Library4 min drive
  • Popular LocationWoodstock Music Shop4 min drive
  • Popular LocationOverlook Mountain Trailhead12 min drive
  • AirportHudson, NY (HCC-Columbia County)51 min drive

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom Guest House

1 King Bed

Guest bedroom main house

2 Single Beds

Living room guest house

1 Double Sofa Bed

Main Bedroom main house

1 Queen Bed

2 bathrooms

Bathroom guest house

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo

Bathroom main house

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining Area

About this property

Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.

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, 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, 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!

Property manager

Erica O'Neill

Amenities

Pool
Hot tub
Pet-friendly
Free WiFi
Air conditioning

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed
No more than 8 people total including the guests

Pets

Pets allowed: dogs less than 20 lb per pet (limit one pet total)
Please message me to get permission first

Smoking

Smoking is not permitted
There is a fee for well-behaved dogs. Please messa
Guests staying long term are required to have the
All garbage and recycling to be properly bagged an

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: no more than 8 people total including the guests
Safety features at this property include a fire extinguisher and a first aid kit

We should mention

A car is recommended for transport to and from this property

About the area

Bearsville

Located in Bearsville, this lodge is in a rural area. Hunter Mountain and Kaaterskill Falls are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Catskill Mountains. Travelling with kids? Consider Woodstock Music Shop, or check out an event or a game at Dietz Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Bearsville, NY

What's nearby

  • Woodstock Public Library - 4 min drive
  • Woodstock Music Shop - 4 min drive
  • Woodstock Golf Club - 5 min drive
  • Bethel Woods Museum - 11 min drive
  • Overlook Mountain Trailhead - 12 min drive

Getting around

  • Rhinecliff-Kingston Station - 31 min drive
  • Hudson, NY (HCC-Columbia County) - 52 min drive

Restaurants

  • Colony - 4 min drive
  • Bread Alone - 4 min drive
  • Olive's Country Store & Cafe - 16 min drive
  • Silvia - 4 min drive
  • Veggie Oasis - 17 min drive

Frequently asked questions

Does Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 20 lb per pet.

What time is check-in at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.?

Check-in begins at 3:00 PM.

What time is check-out at Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.?

Checkout is at 11:00 AM.

Where is Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting. located?

This family-friendly Bearsville lodge is located in a rural location, within 3 mi (5 km) of Woodstock Public Library, Woodstock Music Shop and Byrdcliffe Barn. SweetHeart Gallery and Woodstock Golf Club are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 52 out of 54 reviews" "
Rating 8 - Good. 2 out of 54 reviews" "
Rating 6 - Okay. 0 out of 54 reviews" "
Rating 4 - Poor. 0 out of 54 reviews" "
Rating 2 - Terrible. 0 out of 54 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Katherine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy
It rained most for most of our stay, so it was quite cozy staying indoors. The fireplace and turntable were a plus!
Stayed 3 nights in Apr 2024

10/10 Excellent

Dori B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
tranquil paradise
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.
Stayed 29 nights in Jul 2023

10/10 Excellent

Ayesah H., New York City

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely wonderful!
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!
Stayed 5 nights in Aug 2023

10/10 Excellent

pete g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Weekend Getaway
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.
Stayed 2 nights in Oct 2021

8/10 Good

Erin G.

Liked: Cleanliness, check-in, communication, location
Beautiful property w/ many rules
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.
Stayed 7 nights in Aug 2021

About the host

Hosted by Erica O'Neill

Host profile image
A painter who has long loved the Woodstock area.

Why they chose this property

Charm Charm Charm, Built by the neighboring farmer's family in 1930 for an emigre family from Germany. It has a woodsy feel with charming little details. When we first saw it it was the setting that grabbed us, it's not grand but super relaxed and now a little lux with the new bathrooms and kitchens and the addition of the new hot tub and heated saline pool. The Hamlet of Bearsville has green hills and dark starry nights.
Come and rejuvenate yourself in the relaxing compound, set in landscaped grounds surrounded by flowering apple and magnolia trees.

What makes this property unique

You are in the country with all delicious benefits, from the farm next door where you can walk over in the morning and buy your happy eggs, to outdoorsy activities like swimming holes, hiking, tubing & trout fishing, yet close to everything you would need to have a relaxing time, with art galleries, Zagat rated restaurants, a cute little village for a stroll and some shopping and the relaxed atmosphere of a cosmopolitan environment in this historic arts community walkable to cocktails at the Bearsville Cafe compound.
Tell us how we can improve our siteShare feedback

More Holiday Rentals ideas

People also search for