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

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Woodstock holiday rentals

Property grounds

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (298 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$2,425 total
includes taxes & fees
28 Sept - 29 Sept
Streamside Cottage Half Mile to Town of Woodstock
Exterior

2. 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 HK$1,569
HK$2,644 total
includes taxes & fees
27 Sept - 28 Sept
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
Terrace/patio

3. 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 HK$1,419
HK$2,459 total
includes taxes & fees
22 Sept - 23 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Outdoor dining

4. 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 HK$2,667
HK$5,921 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Mid-Century Retreat with Spa Hot Tub
Interior

5. 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 HK$4,777
HK$7,994 total
includes taxes & fees
11 Oct - 12 Oct
Woodstock Historic Artist Estate - The Museum House
Private kitchen

6. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (11 reviews)
"Oh, I gave this property excellent scores for all the questions but I am reminded now by the suggestions for what to write about about the fact that it listed an Ocean view, which is obviously a mistake. It’s nowhere near the ocean. There’s no ocean view. It is in the woods it’s secluded.I actually took a very little walk in the middle of the night in the dark using my cell phone flashlight and got kind of lost for a while, but managed to find my way back. That was quite an interesting...
United States
Michael H.
The price is HK$894
HK$1,590 total
includes taxes & fees
17 Sept - 18 Sept
Woods Cabin-Kingston/Woodstock, NY.
Interior

7. 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, (100 reviews)
"Wonderful stay. "
United States
Chris L.
The price is HK$1,341
HK$2,108 total
includes taxes & fees
24 Sept - 25 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Outdoor dining

8. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is HK$1,747
HK$2,132 total
includes taxes & fees
17 Sept - 18 Sept
Gatherwild Ranch
Exterior

9. 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, (297 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
The price is HK$1,326
HK$1,770 total
includes taxes & fees
17 Sept - 18 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

10. '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, (51 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 HK$882
HK$1,164 total
includes taxes & fees
23 Sept - 24 Sept
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Terrace/patio

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

West Wing - a unique private space w/patio
Shokan
10.0 out of 10, Exceptional, (33 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
The price is HK$988
HK$1,555 total
includes taxes & fees
22 Sept - 23 Sept
West Wing - a unique private space w/patio
Interior

12. 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$627
HK$2,047 total
includes taxes & fees
23 Sept - 24 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
Property grounds

13. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (33 reviews)
"Excellent stay"
United States
Laura S.
The price is HK$1,588
HK$2,893 total
includes taxes & fees
17 Sept - 18 Sept
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Private kitchen

14. 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 HK$565
HK$1,968 total
includes taxes & fees
27 Sept - 28 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

15. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (17 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is HK$1,177
HK$2,100 total
includes taxes & fees
24 Sept - 25 Sept
Stunning and Cozy loft apartment in kingston .
Private kitchen

16. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (313 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
The price is HK$980
HK$1,098 total
includes taxes & fees
17 Sept - 18 Sept
Starlite Motel
Outdoor spa tub

17. Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Phoenicia
9.8 out of 10, Exceptional, (33 reviews)
"Great place "
United States
Lisa R.
The price is HK$1,200
HK$1,520 total
includes taxes & fees
17 Sept - 18 Sept
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Children’s area

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, (3 reviews)
"Friendly host accommodated all our requests. House is quaint and well-kept and well-stocked for all possible needs."
United States
Simon R.
The price is HK$1,412
HK$3,397 total
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Bar (on property)

19. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"Great location. As advertised. Great value."
United States
Dan
The price is HK$926
HK$1,578 total
includes taxes & fees
17 Sept - 18 Sept
Jessie's Harvest House
Dining

20. Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (19 reviews)
"This was a beautiful little spot and had everything! We loved our 3 night stay."
United States
Holly
The price is HK$1,647
HK$4,060 total
includes taxes & fees
17 Sept - 18 Sept
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Everything was so smooth, from the detailed map and heads up of possible cell service interruptions, to the check in and check out process, housekeeping request, and the ease of communication via text. It was a perfect getaway, minimal interruptions, yet easy to reach with quick responses. Although I could tell there were other guests in cabins nearby because I would see parked cars, it was so quiet that I felt like I was truly there alone! They thought of everything as far as cookware, plates, cups for cold and hot drinks, and utensils. S’mores, snacks, water, coffee, tea, and use of firepit/firewood were all complimentary. There’s a fridge but no microwave which I was not expecting but useful to know. Bring seasoning if you plan to cook. Bring mosquito repellant. It was weird not having a sink in the bathroom but it wasn’t a big deal for me. Would definitely book again!"
crystal 2-night trip
Posted 3 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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
  • Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

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?

Swim. Float. Fish. on private waterfront w/Hot Tub.Fire Pit.Views. Hiking.Games.: This holiday home rental outside of Woodstock is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. It offers a patio, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Woodstock Music Shop and Catskill State Park.

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.