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Woodstock, New York, United States of America
Photo by Marina Timo

Woodstock vacation rentals

We found 730 vacation rentals — enter your dates for availability

Discover a selection of 500 vacation rentals in Woodstock, NY 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 $99 per night, and houses and cabins are popular options for a stay in Woodstock. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Woodstock
Stayed Sep 2021

Excellent!

Exceeded expectations! The property was absolutely beautiful (bigger and even more vibrant than the photos)! Susan made sure to stock the cabin with all of the essentials (coffee, tea, wine opener, etc). About a 5 minute drive to the town of Woodstoc...

Lexi W.
Lexi W.
Stayed Sep 2021

A lovely retreat

We so enjoyed this charming, peaceful cottage. Can’t say enough good things about the beautiful yard, and the babbling stream was an added bonus. Everything was as pictured, and it was so nice to sit outside and watch the wood chucks and the ducks! T...

Kate F.
Kate F.
Stayed Sep 2021

feeling groovy

Right in the heart of downtown Woodstock. Large apartment with well-equipped kitchen. A great place for a weekend stay. The wifi was not great so it would be a difficult place for an extended stay if you need to work virtually. Jeff and Audrey, the ...

Patricia T.
Patricia T.
Stayed Sep 2021

Amazing Stay!!!

This place was awesome drive there and park the car! Walking distance from everything. Place was super clean beds and pillows were very very comfortable. Extra linens at your disposal and kitchen was stocked with dishes and utensils. Will definitely ...

john b.
john b.
Stayed Sep 2021

A Slice of Heaven

Check-in was easy, Richard greeted us upon arrival to give us the lay of the land. The chalet was adorable, very clean and orderly and super cozy. Set on a secluded cul de sac about a five minute drive from the center of town where there is plenty of...

Ryan T.
Ryan T.
Stayed Sep 2021

Woodstock Girls Weekend

We arrived after dark and initially thought we were entering a horror movie driving into the dark woods. Til we saw how beautiful the house was! The house was more beautiful than the photos. Everything we could neee was there. The hot tub was amazing...

Jessica H.
Jessica H.
Stayed Sep 2021

Great house in a charming little town

We were in town for my wife's family reunion. We've used VRBO many times with varying results. This property was one of the best we've ever rented. The condition of the home was spectacular, the location right in the downtown area of Woodstock was co...

Martin B.
Martin B.
Stayed Sep 2021

Cozy cottage in a wooded setting

What a great cottage in a beautiful setting! It was very clean, attractively decorated, the bathrooms had nice, individual bath products (unexpected bonus!), a very large kitchen with windows all around to take in the setting (we watched deer walk by...

Susan C.
Susan C.

Find the best place to stay — Woodstock

Wydeclove Artist Retreat

Sleeps 2 · 1 Bedroom · 1 Bathroom
$250 avg/night
(10)

Romantic Luxury Chalet for 2 with Private Pool

Sleeps 2 · Studio · 1 Bathroom
$282 avg/night
(193)

Streamside Cottage Walking Distance to Town of Woodstock

Sleeps 4 · 1 Bedroom · 1 Bathroom
$217 avg/night
(106)

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

Sleeps 2 · Studio
$130 avg/night
(102)

Village Center: Gracious & Spacious Retreat "Above the Books"

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$152 avg/night
(117)

Hotel Woodstock - Daisy Suite

Sleeps 2 · 1 Bedroom · 1 Bathroom
$99 avg/night
(13)

Search 730 vacation rentals

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How many vacation rentals are available around Woodstock, NY?

Our 2021 property listings offer a large selection of 730 vacation rentals around Woodstock. From 542 house rentals to 108 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Woodstock?

Vrbo offers a large selection of vacation rentals near lovely places in Woodstock. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Karma Triyana Dharmachakra Monastery: 1,123 vacation rentals
  • Overlook Mountain Trailhead: 1,051 vacation rentals
  • Woodstock Golf Club: 1,022 vacation rentals
  • Woodstock Public Library: 1,062 vacation rentals
  • SweetHeart Gallery: 1,041 vacation rentals

But there are many other points of interest around Woodstock listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Woodstock?

Yes, of course. Vrbo has 542 Houses in Woodstock. Our other popular types of vacation rentals in Woodstock include:

  • Cabins: 108 rentals available
  • Cottages: 92 rentals available
  • Farmhouses: 19 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 Woodstock?

Yes, you can select your preferred vacation rental with pool among our 129 vacation rentals with pool available in Woodstock. Please use our search bar to access the selection of vacation rentals available.

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