Photo by Robert Morra

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Woodstock holiday rentals

A stone wall beside a flowing river, surrounded by trees and a wooden cabin.

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (309 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 HK$1,122
HK$2,362 total
includes taxes & fees
16 Nov - 17 Nov
Streamside Cottage Half Mile to Town of Woodstock
A modern living room with a large window, a dining area with a round table, and a cozy seating area with a fur throw.

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 HK$1,329
HK$3,622 total
includes taxes & fees
8 Nov - 9 Nov
Woodstock Historic Artist Estate - The Carriage House
A house with a sloped roof, a front porch with two chairs, and a well-maintained lawn.

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 HK$1,568
HK$2,415 total
includes taxes & fees
8 Nov - 9 Nov
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

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 HK$2,031
HK$3,903 total
includes taxes & fees
10 Nov - 11 Nov
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A spacious living room with a large window, a modern sofa, a coffee table, and a bookshelf.

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 HK$4,015
HK$6,736 total
includes taxes & fees
11 Nov - 12 Nov
Woodstock Historic Artist Estate - The Museum House
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

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.
Cozy Mid-Century Retreat with Spa Hot Tub
A bedroom with a large window, a bed, a lamp, and a view of a park.

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 HK$4,579
HK$7,754 total
includes taxes & fees
15 Nov - 16 Nov
Woodstock historic artist estate - The Pond House
Private kitchen

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 HK$968
HK$1,602 total
includes taxes & fees
10 Nov - 11 Nov
Woods Cabin-Kingston/Woodstock, NY.
A wooden deck with a bench, surrounded by a forested area.

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 HK$1,097
HK$1,633 total
includes taxes & fees
8 Nov - 9 Nov
West Wing - a unique private space w/patio
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

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 HK$1,415
HK$2,085 total
includes taxes & fees
29 Nov - 30 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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 HK$596
HK$1,835 total
includes taxes & fees
18 Nov - 19 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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 HK$588
HK$1,914 total
includes taxes & fees
9 Nov - 10 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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, (340 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is HK$1,192
HK$1,625 total
includes taxes & fees
7 Dec - 8 Dec
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

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 HK$674
HK$2,151 total
includes taxes & fees
18 Nov - 19 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

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 HK$868
HK$1,965 total
includes taxes & fees
9 Nov - 10 Nov
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

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 HK$797
HK$1,920 total
includes taxes & fees
9 Nov - 10 Nov
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A bedroom with a large window, wooden ceiling, and a bed with white bedding and two decorative pillows.

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, (19 reviews)
"Wonderful spot to unwind and take a relaxing getaway."
United States
cheryll s.
The price is HK$1,482
HK$3,117 total
includes taxes & fees
8 Nov - 9 Nov
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

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 HK$1,176
HK$2,002 total
includes taxes & fees
9 Nov - 10 Nov
Stunning and Cozy loft apartment in kingston .
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

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 HK$870
HK$1,408 total
includes taxes & fees
8 Nov - 9 Nov
Jessie's Harvest House Suite
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

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 HK$925
HK$1,501 total
includes taxes & fees
8 Nov - 9 Nov
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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Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
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Look no further and take a look at our great range of rental properties in Woodstock!

Frequently Asked Questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals close to the most popular sights in Woodstock, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Woodstock has to offer?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This holiday 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 holiday rentals are there in Woodstock?

Expedia has 75 holiday 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 holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.