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, (308 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is CA $200
CA $421 total
includes taxes & fees
Nov 10 - Nov 11
Streamside Cottage Half Mile to Town of Woodstock

2. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House
Woodstock
9.8 out of 10, Exceptional, (51 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
The price is CA $210
CA $591 total
includes taxes & fees
Nov 5 - Nov 6
Woodstock Historic Artist Estate - The Carriage House

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

Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
Woodstock
9.0 out of 10, Wonderful, (2 reviews)
"Great location."
United States
Louis
The price is CA $280
CA $431 total
includes taxes & fees
Nov 8 - Nov 9
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

4. A pleasant space in a pleasant neighborhood in a beautiful part of the country!

A pleasant space in a pleasant neighborhood in a beautiful part of the country!
Woodstock
10.0 out of 10, Exceptional, (9 reviews)
"Very nice property that met our needs perfectly. Clean and very well maintained rooms. Lots of wildlife, beautiful wooded area. Peter, the host, was lovely and helpful."
United States
Barbara A.
The price is CA $362
CA $698 total
includes taxes & fees
Nov 9 - Nov 10
A pleasant space in a pleasant neighborhood in a beautiful part of the country!

5. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
9.8 out of 10, Exceptional, (16 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 $766
CA $1,214 total
includes taxes & fees
Nov 11 - Nov 12
Woodstock Historic Artist Estate - The Museum House

6. Cozy Mid-Century Retreat with Spa Hot Tub

Cozy Mid-Century Retreat with Spa Hot Tub
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"Great spot, close to town but removed enough to have total privacy. Thank you!"
United States
Alec M.
The price is CA $475
CA $1,001 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Mid-Century Retreat with Spa Hot Tub

7. Woodstock historic artist estate - The Pond House

Woodstock historic artist estate - The Pond House
Woodstock
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful host, outstanding location, very nice and creative home. We very much enjoyed our stay, and look forward to coming back again!"
United States
Joe V.
The price is CA $403
CA $824 total
includes taxes & fees
Nov 5 - Nov 6
Woodstock historic artist estate - The Pond House

8. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (17 reviews)
"We loved the little cabin in the woods!"
United States
Patti G.
The price is CA $173
CA $283 total
includes taxes & fees
Nov 10 - Nov 11
Woods Cabin-Kingston/Woodstock, NY.

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (40 reviews)
"Clean and beautifully decorated room. Very comfortable, excellent bed and linens. Friendly and knowledgeable staff. An "out of the way " place and that's its charm, yet close enough - short car rides- to restaurants and other attractions. We'd gladly return!"
United States
Ronald
The price is CA $196
CA $288 total
includes taxes & fees
Nov 8 - Nov 9
West Wing - a unique private space w/patio

10. 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, (110 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is CA $252
CA $375 total
includes taxes & fees
Nov 9 - Nov 10
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is CA $106
CA $341 total
includes taxes & fees
Nov 17 - Nov 18
Campfire Cottage: Fireplace, fire pit & no chores!

12. 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, (7 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 $105
CA $340 total
includes taxes & fees
Nov 9 - Nov 10
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

13. 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, (335 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is CA $213
CA $290 total
includes taxes & fees
Dec 3 - Dec 4
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

14. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is CA $120
CA $401 total
includes taxes & fees
Nov 17 - Nov 18
Retro Retreat: renovated 2BR, desk, no chore list!

15. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
The price is CA $159
CA $355 total
includes taxes & fees
Nov 16 - Nov 17
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

16. 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, (39 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is CA $151
CA $350 total
includes taxes & fees
Nov 16 - Nov 17
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

17. PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Mt. Tremper
9.8 out of 10, Exceptional, (18 reviews)
"Wonderful spot to unwind and take a relaxing getaway."
United States
cheryll s.
The price is CA $264
CA $556 total
includes taxes & fees
Nov 8 - Nov 9
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

18. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is CA $210
CA $356 total
includes taxes & fees
Nov 5 - Nov 6
Stunning and Cozy loft apartment in kingston .

19. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
The price is CA $131
CA $230 total
includes taxes & fees
Nov 15 - Nov 16
Jessie's Harvest House Suite

20. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is CA $165
CA $266 total
includes taxes & fees
Nov 5 - Nov 6
Jessie's Harvest House
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?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Woodstock is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Bearsville Theater and Colony. 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.