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Vacation rentals in Bearsville

Vacation rentals in Bearsville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Bearsville

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Relax on the Ridge - 2 miles from Woodstock
    SUPERHOSTEntire guesthouse · 4 guests · 1 bed · 1 bath
    Relax on the Ridge - 2 miles from Woodstock

    Stay and relax in a private guest house on a 5+ acre property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet only 2 miles from Woodstock and 10 miles from Phoenicia. Relax on the grounds while watching our Tennessee Mountain and Cashmere goats graze or drive into town to enjoy shops, restaurants, and swimming holes.

    What guests are saying:

    “This was an incredible stay. Paul and Kara were very accommodating and we’re so grateful! They were quick to respond to any of our questions. The place itself is beautiful and very comfortable. We stayed for two weeks and found everything we needed. There were plenty of linens, pillows and towels. While there is no formal kitchen, were able to do a lot with a hot plate, a toaster oven and the pans available. I loved the little touches in the house such as the tea and sugar. The views from the bedroom and living room windows were stunning. We were able to explore the surrounding grounds and take in some nature. I can’t say enough about the goats! They were an absolute delight and my favorite part of this trip. It was a great place to retreat to, very clean and relaxing. Highly recommend!”

  • Cozy country cottage
    Entire cottage · 4 guests · 2 beds · 1 bath
    Cozy country cottage

    Cozy cottage near the stream with open plan living, fireplace, great mountain view and easy access to skiing, shopping, restaurants and entertainment

  • Chestnut Hill Hideaway
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Chestnut Hill Hideaway

    The Space Experience an authentic bohemian Woodstock handmade house from the 60's, updated and modernized. Tucked away in the woods, yet minutes to town, you will enjoy both privacy and convenience while being in nature. Come relax in privacy and enjoy cocktails on your deck overlooking the forest. Wake up to the sound of birds and unwind in the soaking tub in your spacious bathroom. Take a walk down the country road...serenity and tranquility await you.

    What guests are saying:

    “My boyfriend and I had a wonderful stay at Benjamin's cute, homey apartment in Woodstock. The location was prime, privacy from neighbors in the middle of the woods (we had some fun watching the chipmunks and a deer roaming in the backyard), yet only a 5-7 minute drive to downtown. Self check in/check out was super easy and Benjamin was there to assist and answer any questions we had and had great recommendations for things to do in the area. The bed was very, very comfy and we each enjoyed taking a hot bath in the soaking tub after a long winter hike in the Catskills. The one negative thing is that the mini fridge is a little finicky and didn't keep our leftovers very well, but all the other amenities made up for it (he even had contact solution there). Would definitely recommend this place to anyone looking for a nice, tranquil getaway from the city!”

Vacation rentals for every style

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  • Homes
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Popular amenities for Bearsville vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Bearsville

Woodstock cabin 3 miles from town
SUPERHOSTEntire cabin
Woodstock cabin 3 miles from town
Price:$172 CAD/night
Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace
SUPERHOSTEntire guesthouse
Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace
Price:$156 CAD/night
Just Be Byrdcliffe
SUPERHOSTEntire guest suite
Just Be Byrdcliffe
Price:$176 CAD/night
The Carriage House: Studio
SUPERHOSTEntire guesthouse
The Carriage House: Studio
Price:$115 CAD/night
MTN.SIDE Retreat-Woodstock-Ski-Hike
SUPERHOSTEntire apartment
MTN.SIDE Retreat-Woodstock-Ski-Hike
Price:$196 CAD/night
Stylish Woodstock Guest House..Mountain Views
SUPERHOSTEntire guesthouse
Stylish Woodstock Guest House..Mountain Views
Price:$264 CAD/night
Catskills 2 br Cottage
SUPERHOSTEntire cottage
Catskills 2 br Cottage
Price:$123 CAD/night
Woodstock Charmer
SUPERHOSTEntire bungalow
Woodstock Charmer
Price:$203 CAD/night
Hotel Woodstock - Iris Suite
SUPERHOSTEntire apartment
Hotel Woodstock - Iris Suite
Price:$80 CAD/night
Comfortable Woodstock Getaway
SUPERHOSTEntire house
Comfortable Woodstock Getaway
Price:$129 CAD/night
Creekfront Cottage between Phoenicia & Hunter Mtn.
SUPERHOSTEntire cottage
Creekfront Cottage between Phoenicia & Hunter Mtn.
Price:$149 CAD/night
The Woodstock Barn Studio
SUPERHOSTBarn
The Woodstock Barn Studio
Price:$149 CAD/night
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