A calm lake with a sunset reflecting on the water, surrounded by forested hills.

Woodstock Vacation Rentals

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Our top choices for Woodstock vacation rentals

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (291 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveller
The price is CA $227
CA $476 total
includes taxes & fees
Aug 11 - Aug 12
Streamside Cottage Half Mile to Town of Woodstock

2. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is CA $281
CA $470 total
includes taxes & fees
Aug 31 - Sep 1
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

3. Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
Woodstock
10.0 out of 10, Exceptional, (1 review)
"The setting was peaceful and cottage was adorable. The proximity to Tinker Street was a short walk."
United States
Susan
The price is CA $281
CA $477 total
includes taxes & fees
Aug 10 - Aug 11
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

4. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (12 reviews)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
The price is CA $1,426
CA $2,165 total
includes taxes & fees
Aug 16 - Aug 17
Woodstock Historic Artist Estate - The Museum House

5. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (95 reviews)
"Wonderful stay. "
United States
Chris L.
The price is CA $215
CA $343 total
includes taxes & fees
Sep 3 - Sep 4
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

6. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (7 reviews)
"The cabin is awesome. Surrounded by forrest you feel like youre the only person in the world. What's even cooler is its off grid but you dont miss a thing. Lights. Music. Bathroom. There were even a couple board games. Outside fire ready to go. Exactly what I was looking for."
United States
Carrie
The price is CA $160
CA $282 total
includes taxes & fees
Aug 9 - Aug 10
Woods Cabin-Kingston/Woodstock, NY.

7. 'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
8.0 out of 10, Very good, (47 reviews)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is CA $158
CA $208 total
includes taxes & fees
Aug 12 - Aug 13
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8. West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (28 reviews)
"I enjoyed my stay at this lovely, clean, cozy home."
United States
Taela
The price is CA $177
CA $277 total
includes taxes & fees
Aug 6 - Aug 7
West Wing - a unique private space w/patio

9. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is CA $100
CA $346 total
includes taxes & fees
Aug 10 - Aug 11
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

10. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (265 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is CA $280
CA $363 total
includes taxes & fees
Aug 12 - Aug 13
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

11. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is CA $155
CA $424 total
includes taxes & fees
Aug 19 - Aug 20
Campfire Cottage: Fireplace, fire pit & no chores!

12. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (33 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is CA $171
CA $393 total
includes taxes & fees
Aug 11 - Aug 12
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

13. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (308 reviews)
"Very nice for the price. The full kitchen was great stocked with plates, glasses, pans etc. The beds seemed new and very comfortable and the bathroom was brand new and exceptionally nice. They have definitely been putting effort into updating the rooms and it shows. I would definitely stay there again."
United States
Sean
The price is CA $176
CA $197 total
includes taxes & fees
Aug 12 - Aug 13
Starlite Motel

14. Jessie's Harvest House

Jessie's Harvest House
Tannersville
10.0 out of 10, Exceptional, (4 reviews)
"Great location. As advertised. Great value."
United States
Dan
The price is CA $219
CA $342 total
includes taxes & fees
Sep 2 - Sep 3
Jessie's Harvest House

15. Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (18 reviews)
"This was a beautiful little spot and had everything! We loved our 3 night stay."
United States
Holly
The price is CA $246
CA $669 total
includes taxes & fees
Aug 20 - Aug 21
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

16. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (17 reviews)
"The apartment was very clean and updated! Small back deck was nice to drink my morning coffee! Only issue was kids yelling and screaming in the neighborhood till almost 11pm."
United States
Donna
The price is CA $211
CA $370 total
includes taxes & fees
Sep 3 - Sep 4
Stunning and Cozy loft apartment in kingston .

17. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (12 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is CA $204
CA $370 total
includes taxes & fees
Aug 12 - Aug 13
Charming loft cottage in tranquil Germantown with WiFi, AC

18. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Haines Falls
10.0 out of 10, Exceptional, (1 review)
"House was clean and well kept, perfect for our family weekend trip!"
United States
Edward C.
The price is CA $177
CA $511 total
includes taxes & fees
Aug 12 - Aug 13
Cozy 2-bedroom house in Haines Falls near Katterskill falls .

19. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (32 reviews)
"Excellent stay"
United States
Laura S.
The price is CA $285
CA $525 total
includes taxes & fees
Aug 19 - Aug 20
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

20. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here. It was a beautiful location and central to the places we wanted to visit. It looked brand new and it was very clean. It was quiet and peaceful. The hosts even had little snacks for us which was a nice touch."
United States
Laura M.
The price is CA $336
CA $621 total
includes taxes & fees
Aug 12 - Aug 13
Peaceful Riverfront Cottage with Private Hot tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Woodstock Hotel Reviews

Find out more about Woodstock

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woodstock. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there vacation rentals in Woodstock?

Yes, there are vacation rentals close to well known attractions in Woodstock, or you can choose a more secluded option if you want a relaxing place to stay. The forests and art scene are just a few reasons why tourists like Woodstock. Make sure you have time to check out the riverfront and mountain views during your trip.

What's the top vacation rental in Woodstock?

The Studio at the Inn at High Falls: This vacation home rental outside of Woodstock is located in a rural location and offers a garden, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals are there in Woodstock?

Expedia has 75 vacation rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Enjoy the outdoors at Overlook Mountain Trailhead and The Comeau Property, or simply take in cultural attractions like Colony and Levon Helm Studios. Other places in town to visit include Catskill State Park and Woodstock Music Shop.

What are vacation rentals like in Woodstock?

Vacation rentals are privately owned properties you can reserve for several days or longer in Woodstock. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.