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Vacation rentals in Woodstock

Vacation rentals in Woodstock

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Woodstock

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

  • Chestnut Hill Hideaway
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    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!”

  • Woodstock Historic Artist Estate - The Pond House
    PlusEntire house · 5 guests · 3 beds · 1.5 bathrooms
    Woodstock Historic Artist Estate - The Pond House

    Awaken to an idyllic view of trees through timber-framed picture windows. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. Today the former artist studio of the estate is an architect-renovated gem most recently featured at Icon Design Magazine Italy. The setting with a private waterfall bordering public preserves, as well as the attention to architectural detail is unique.

    What guests are saying:

    “The Pond House was an INCREDIBLE getaway and Nin was so warm and easy to communicate with. We stayed here during the covid-19 outbreak and i so appreciated her taking extra precaution to make sure we were practicing all social isolation rules before accepting my booking, as well as sharing her plans for disinfecting the house between guests -- it was so assuring to know we were on the same page, and this made me feel very comfortable given the strange circumstance. And the property the house sits on is GORGEOUS. The views from the master bed (so comfy) was breathtaking -- you literally fall asleep to the stars and wake up birdwatching over the pond from your bed. There are so many treasures to enjoy -- the rock by the waterfall, stream hike, fire pit..... so, so good! :)”

  • Hotel Woodstock - Aster Suite
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    Hotel Woodstock - Aster Suite

    Overlooking the Woodstock village center, this antique hotel has 148 years of history and charm. From the front steps you will feel the same energy that travelers have felt since President Ulysses S. Grant visited Woodstock in 1872. This room 2A is a studio apartment with a balcony that overlooks the center of the village. There is a full kitchen and a private bath. You do not need a car! The Trailways bus from NYC stops directly across the street, and walk to everything in the village.

    What guests are saying:

    “My stay at the Aster suite was wonderful. The suite has a very warm and comfortable environment to it and it welcomed me as soon as I entered the door. Everything that I needed for my stay was available to me in the suite and that was great. Also the balcony view of the town you get from the suite is amazing. It was nice to sit up there and look out on the town of Woodstock. Ann and Dave were very helpful and quick to respond on any questions I had and that made my stay even better. I would recommend this place to anyone looking to have an enjoyable place to stay that is located right in the center of Woodstock.”

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Popular amenities for Woodstock holiday rentals

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

Other great holiday rentals in Woodstock

Woodstock Historic Artist Estate - The Pond House
PlusEntire house
Woodstock Historic Artist Estate - The Pond House
Price:₹29,636 / night
Ophelia - Classic Woodstock Artist House
SUPERHOSTEntire house
Ophelia - Classic Woodstock Artist House
Price:₹11,254 / night
Chestnut Hill Hideaway
SUPERHOSTEntire flat
Chestnut Hill Hideaway
Price:₹7,503 / night
Hotel Woodstock - Aster Suite
SUPERHOSTEntire flat
Hotel Woodstock - Aster Suite
Price:₹3,984 / night
Woodstock cabin 3 miles from town
SUPERHOSTEntire cabin
Woodstock cabin 3 miles from town
Price:₹9,228 / night
The Carriage House: Studio
SUPERHOSTEntire guest house
The Carriage House: Studio
Price:₹7,128 / night
Just Be Byrdcliffe
SUPERHOSTEntire guest suite
Just Be Byrdcliffe
Price:₹9,754 / night
Romantic Cottage on the Stream, Walk to Town
SUPERHOSTEntire cottage
Romantic Cottage on the Stream, Walk to Town
Price:₹13,505 / night
WOODSTOCK VILLAGE COUNTRY HOME
SUPERHOSTEntire house
WOODSTOCK VILLAGE COUNTRY HOME
Price:₹12,004 / night
2BR Rental in Woodstock SPA
SUPERHOSTEntire flat
2BR Rental in Woodstock SPA
Price:₹18,757 / night
Magical Chalet w/ spectacular views
SUPERHOSTEntire house
Magical Chalet w/ spectacular views
Price:₹45,016 / night
Woodstock Historic Artist Estate - Cottage House
PlusEntire house
Woodstock Historic Artist Estate - Cottage House
Price:₹16,881 / night
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