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Bearsville, New York, United States of America

Bearsville vacation rentals

We found 335 vacation rentals — enter your dates for availability

Discover a selection of 335 vacation rentals in Bearsville that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $100 per night, and houses and cabins are popular options for a stay in Bearsville. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 258 Houses

Cabins

View 68 Cabins

Cottages

View 62 Cottages

Bungalows

View 62 Bungalows

Condos/Apartments

View 29 Condos/Apartments

Studios

View 29 Studios

Find the best place to stay — Bearsville

Woodstock Villa / Tuscan inspired private oasis, heated pool, 5 min to Woodstock

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
$563 avg/night

Private Mid Century Retreat with Pool & Mountain Views

Sleeps 6 · 4 Bedrooms · 3 Bathrooms
$850 avg/night

Streamside Cottage Walking Distance to Town of Woodstock

Sleeps 4 · 1 Bedroom · 1 Bathroom
$210 avg/night
(118)

NEW! Rock City Writer's Studio: Bucolic Setting, Nordic Sauna, Walk to Town!

Sleeps 2 · Studio · 1 Bathroom
$125 avg/night
(105)

Beautiful, Tranquil Woodstock Mountain House with Hot Tub and Ping Pong

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$320 avg/night
(139)

BLUEBERRY HILL CABIN

Sleeps 2 · 1 Bedroom · 1 Bathroom
$100 avg/night
(8)

Search 335 vacation rentals

Top rated rentals — Bearsville
Stayed Apr 2022

Even better than we expected

This is a lovely house, cleverly designed, beautifully furnished and well maintained, with every accessory you'd ever need and more. There are a few minor quirks as you'd expected in a unique house. The setting is beyond beautiful--private, quiet, wi...

Paul C.
Paul C.
Stayed Apr 2022

Perfectly peaceful!

I loved my stay at the cabin! It was the perfect little weekend retreat and having the stream right out back was incredible. And it wasn't too far from Woodstock. Eugenia was easy to communicate with and responded quickly to my questions. I'd love to...

Carrie Z.
Carrie Z.
Stayed Apr 2022

Amazing Catskills Retreat

This property was nothing short of amazing! Great location - short drive to town, end of quiet road, and beautiful mountain views. Property has several areas for family/friends to gather. House was super clean and stocked with all the necessary essen...

Kevin C.
Kevin C.
Stayed Apr 2022

Excellent stay in Woodstock

My husband and I stayed in this charming 2 bedroom flat above a spiritual book store - Miribai in Woodstock. Apparently popular among the locals. The flat was very charming, and was a perfect respite in between our busy activities. Including coming b...

JESSICA M.
JESSICA M.

NEW YORK

Stayed Apr 2022

Couldn’t be happier.

Everything about this property was exactly what we needed for a perfect getaway. Our original situation changed a bit and David was understanding and accommodating. We are so happy that we found it/ chose it. We did not want to leave and hope to retu...

Beth T.
Beth T.
Stayed Mar 2022

Perfect for a weekend getaway with our dog!

This was such a cute little house that was perfect for me, my husband, and our dog! This guest house is connected to the owner’s house, but honestly we didn’t even hear a peep from his family the whole time, so it felt very private! The location i...

StephKenna
StephKenna
Stayed Mar 2022

ANNIVERSARY WEEKEND

My wife and I stayed here for our anniversary weekend. When we arrived and opened the door, we were in heaven. So modern, clean and gorgeous. Everything about this property is simply amazing! The bed, layout, amenities, fireplace and was just some of...

Casey R.
Casey R.
Stayed Mar 2022

Great Solo Trip

I had a wonderful stay at the property as a solo traveler! Everything was exactly as specified, and I felt like I had everything I needed. It was a perfect few minute drive from town and close by to the other area towns I wanted to visit. It’s worth ...

Katie W.
Katie W.

Buffalo, NY

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How many vacation rentals are available around Bearsville?

Our 2022 property listings offer a large selection of 335 vacation rentals around Bearsville. From 258 house rentals to 68 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Bearsville?

Yes, of course. Vrbo has 258 Houses in Bearsville. Our other popular types of vacation rentals in Bearsville include:

  • Cabins: 68 rentals available
  • Cottages: 62 rentals available
  • Bungalows: 62 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Bearsville?

Yes, you can select your preferred vacation rental with pool among our 76 vacation rentals with pool available in Bearsville. Please use our search bar to access the selection of vacation rentals available.