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Vacation rentals in Woodstock

Vacation rentals in Woodstock

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodstock

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

  • 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!”

  • Woodstock cabin 3 miles from town
    SUPERHOSTEntire cabin · 2 guests · 0 beds · 1 bath
    Woodstock cabin 3 miles from town

    Charming newly renovated cabin in the woods. Full kitchen & bath & wraparound deck. Brand new Macy’s sofa bed w/very firm mattress. Up the hill from Bearsville Theater, Bear Cafe, Commune & Little Bear Chinese restaurants; just down the hill from the Byrdcliffe barn & theater. Five minutes by car to center of town. Peaceful & quiet, with easy access to any Woodstock offering that strikes your fancy--music, art, shopping, hiking, swimming,drumming, meditation--or just hanging out on the deck.

    What guests are saying:

    “A very beautiful guest house adjacent to the main house. The place was sparkling clean and charming with great interior design and comfy wrap around deck with cute little wooden bridge. Even though we showed up right after the snowfall and the hosts were not on property drive way and parking space were well plowed so that we did not have an issue getting in or out. Location is a fairly short drive from local stores and major Catskills through ways which makes it available to use as a short weekend retreat as well as a base for skiing trips. Overall loved the place and will definitely recommend it.”

  • Romantic Cottage on the Stream, Walk to Town
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1 bath
    Romantic Cottage on the Stream, Walk to Town

    The perfect cozy cottage for a romantic getaway...or just to get away. Walking distance to the quaint and funky town of Woodstock. Enjoy coffee or cocktails right on the stream on the back deck or underneath the pergola. Fall asleep to the soothing sounds of the stream and wake up to the beautiful songbirds. Have a BBQ in the lush garden or sit around the fire pit and toast marshmallows. 2% Ulster County tax included. Unfortunately, the indoor fireplace is not working at this time.

    What guests are saying:

    “My partner and I absolutely loved our stay at this romantic cottage. It truly brought us peace in a stressful world. Being right on the babbling brook was so calming and we slept so well. The hosts added so many nice touches such as fresh picked wildflowers in the kitchen. We also loved cooking on the grill and making a firepit at night and sitting under the stars. Also the shower with the skylight was fabulous. It felt like a spa shower! I would 100 percent recommend this place to friends. It was the perfect getaway from the city.”

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Popular amenities for Woodstock vacation rentals

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

Other great vacation rentals in Woodstock

Woodstock Historic Artist Estate - Cottage House
SUPERHOSTEntire house
Woodstock Historic Artist Estate - Cottage House
Price:R3,870 ZAR / night
Just Be Byrdcliffe
SUPERHOSTEntire guest suite
Just Be Byrdcliffe
Price:R2,236 ZAR / night
The Carriage House: Garden Apartment
SUPERHOSTEntire guest suite
The Carriage House: Garden Apartment
Price:R1,720 ZAR / night
Restored Farmhouse with Yoga Studio
SUPERHOSTEntire cabin
Restored Farmhouse with Yoga Studio
Price:R7,264 ZAR / night
Hotel Woodstock - Aster Suite
SUPERHOSTEntire apartment
Hotel Woodstock - Aster Suite
Price:R1,187 ZAR / night
Stunning Woodstock 1 BR Hideaway
Entire cottage
Stunning Woodstock 1 BR Hideaway
Price:R3,010 ZAR / night
2BR Rental in Woodstock SPA
SUPERHOSTEntire apartment
2BR Rental in Woodstock SPA
Price:R4,299 ZAR / night
Woodstock Charmer
SUPERHOSTEntire bungalow
Woodstock Charmer
Price:R2,580 ZAR / night
Magical Chalet w/ spectacular views
SUPERHOSTEntire house
Magical Chalet w/ spectacular views
Price:R10,319 ZAR / night
WOODSTOCK VILLAGE COUNTRY HOME
SUPERHOSTEntire house
WOODSTOCK VILLAGE COUNTRY HOME
Price:R2,752 ZAR / night
Relax on the Ridge - 2 miles from Woodstock
SUPERHOSTEntire guesthouse
Relax on the Ridge - 2 miles from Woodstock
Price:R1,462 ZAR / night
Woodstock Serene Retreat
SUPERHOSTEntire house
Woodstock Serene Retreat
Price:R2,872 ZAR / night
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