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

Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Woodstock vacation rentals

A natural setting with a stream, red chairs, and a forested area.

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (301 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.
$303 nightly
The price is $339
Nov 4 - Nov 5
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A house with a sloped roof, a front porch with two chairs, and a well-maintained lawn.

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
$299 nightly
The price is $335
Oct 7 - Oct 8
Total with taxes and fees
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

3. 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 modern kitchen with a central island, black cabinetry, and pendant lighting.

4. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (13 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.
$846 nightly
The price is $948
Oct 12 - Oct 13
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
Private kitchen

5. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (13 reviews)
"The Woods Cabin was exactly what it said it was; a teeny tiny, relatively new cabin pretty deep in the scrubby woods of rural NY. It was clean and fully functional, but it was very basic—it was much more than a tent, but the experience was not at all “glamping.” The owner was exceptionally responsive and helpful…no complaints there, or anywhere! As I said, the Woods Cabin is/was exactly what it said it was. Nothing more; nothing less."
United States
Nora Tracy
$180 nightly
The price is $202
Oct 7 - Oct 8
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

6. 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, (105 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
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.

7. 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.
$239 nightly
The price is $268
Nov 3 - Nov 4
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A wooden deck with a bench, surrounded by a forested area.

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (36 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
$178 nightly
The price is $199
Oct 12 - Oct 13
Total with taxes and fees
West Wing - a unique private space w/patio
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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.
$221 nightly
The price is $248
Oct 14 - Oct 15
Total with taxes and fees
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'.

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, (317 reviews)
"Excellent place"
United States
Yeudin
$201 nightly
The price is $217
Nov 5 - Nov 6
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A bathroom with a shower curtain, a sink, a mirror, and a hairdryer on the wall.

11. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (316 reviews)
"Everything was great"
United States
Danielle
$125 nightly
The price is $140
Oct 12 - Oct 13
Total with taxes and fees
Starlite Motel
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

12. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$230 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
Gatherwild Ranch
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

13. 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
$277 nightly
The price is $310
Nov 2 - Nov 3
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
A sectional sofa with matching ottomans, a small table with a lamp, and a patterned rug on a wooden floor.

14. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
$310 nightly
The price is $347
Oct 27 - Oct 28
Total with taxes and fees
Country House offers 2 bedrooms and a den, lots of parking.
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)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
$247 nightly
The price is $277
Oct 28 - Oct 29
Total with taxes and fees
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, (37 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$289 nightly
The price is $323
Nov 3 - Nov 4
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

17. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
$253 nightly
The price is $286
Nov 3 - Nov 4
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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, (17 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
$239 nightly
The price is $268
Oct 7 - Oct 8
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

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.
$164 nightly
The price is $173
Oct 13 - Oct 14
Total with taxes and fees
Jessie's Harvest House Suite
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

20. Jessie's Harvest House

Jessie's Harvest House
Tannersville
9.0 out of 10, Wonderful, (6 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$190 nightly
The price is $201
Oct 7 - Oct 8
Total with taxes and fees
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

8/10 Good
"."
Alexandra 1-night trip
Posted 10 hours ago
Pocketbook Hotel and Bath

Find out more about Woodstock

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.