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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Woodstock holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is £133
includes taxes & fees
17 Nov - 18 Nov
Fat Sheep Farm & Cabins
A large house with a fire pit and outdoor seating.

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is £157
includes taxes & fees
10 Nov - 11 Nov
Bridgewater Living - Ben&Jerry Suite
A large house with a fire pit and outdoor seating.

3. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is £156
includes taxes & fees
10 Nov - 11 Nov
Bridgewater Living - Ski VT Suite
A sunroom with wicker furniture, large windows, and string lights.

4. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (22 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is £185
includes taxes & fees
15 Nov - 16 Nov
Addie's Place: A Quiet and Quirky Guesthouse
A large house with a fire pit and outdoor seating.

5. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
The price is £372
includes taxes & fees
11 Nov - 12 Nov
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A residential area with houses, a swimming pool, and a mountain backdrop.

6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Place was great"
United States
Nathan H.
The price is £205
includes taxes & fees
10 Nov - 11 Nov
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

7. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great room!"
United States
Carla M.
The price is £203
includes taxes & fees
10 Nov - 11 Nov
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

8. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Host was responsive to questions. Great stay overall."
United States
Riley T.
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

9. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is £209
includes taxes & fees
10 Nov - 11 Nov
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

10. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (25 reviews)
"Great place "
United States
Kathleen M.
The price is £359
includes taxes & fees
10 Nov - 11 Nov
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

11. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
The price is £331
includes taxes & fees
10 Nov - 11 Nov
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A modern cabin with a deck, surrounded by a forest.

12. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
The price is £650
includes taxes & fees
10 Nov - 11 Nov
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

13. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (73 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is £320
includes taxes & fees
10 Nov - 11 Nov
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

14. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (10 reviews)
"Perfect clean space, very comfortable and great location for the week. We were not big fans of the mattress toppers, they kept sliding off, but that is a personal preference matter. Staff communication was 10 out of 10. Highly recommend."
United States
Lisa
The price is £313
includes taxes & fees
10 Nov - 11 Nov
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

15. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
The price is £211
includes taxes & fees
12 Nov - 13 Nov
Mountain Green ground-floor condo with private yard off the patio
A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

16. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (15 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
The price is £252
includes taxes & fees
10 Nov - 11 Nov
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

17. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is £194
includes taxes & fees
10 Nov - 11 Nov
Cozy Village Condo-Okemo Shuttle
A wooden gazebo with a roof, surrounded by lush greenery and flowers.

18. CozyCub -Location, Ski Off/ Shuttle On

CozyCub -Location, Ski Off/ Shuttle On
Killington
9.8 out of 10, Exceptional, (26 reviews)
"Great trip!"
United States
casey d.
The price is £202
includes taxes & fees
10 Nov - 11 Nov
CozyCub -Location, Ski Off/ Shuttle On
A sign for Whifletree with a view of a golf course and mountains in the background.

19. Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"The property was a great location. Close enough for a daily drive to stowe or woodstock. I would highly recommend this place. The only thing I wish I would have known is there are a few flights of stairs to go up and down with luggage. Thanks for a great stay"
United States
Brandy
The price is £285
includes taxes & fees
10 Nov - 11 Nov
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
A wooden cabin interior with a staircase, a sofa, and a table.

20. Adventure Cabin Hot Tub Sauna Trails Game Area

Adventure Cabin Hot Tub Sauna Trails Game Area
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"A very clean and modern cabin. Loved the amenities like the paddle boards, kayaks and hot tub.!"
United States
Katherine B.
The price is £298
includes taxes & fees
11 Nov - 12 Nov
Adventure Cabin Hot Tub Sauna Trails Game Area
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

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
Woodstock

8/10 Good

I always thought motels were rather unpleasant and distasteful - well, I could not have been any more mistaken! My partner and I absolutely loved this motel; it was conveniently located, the surroundings were gorgeous and our room was one you would expect to find in a proper nice hotel. It was clean, modern, had a big flat-screen TV and the bed was super comfortable! The level of attention upon arrival and throughout the whole stay was also flawless. We were greeted by Patrick, who is the...
United Kingdom
Angel
Reviewed October 14, 2015
Sleep Woodstock Motel

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as £132 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 holiday.

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.

Frequently Asked Questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Billings Farm and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your holiday.

What are some of the best holiday rentals that Woodstock has to offer?

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town: This highly rated holiday home rental in Woodstock is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Woodstock is Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!.

How many holiday rentals are there in Woodstock?

Expedia has 37 holiday rentals for your stay in Woodstock.

What’s there to see and do in Woodstock?

Cultural attractions include Woodstock Town Hall Theatre and Billings Farm and Museum, whereas Marsh-Billings-Rockefeller National Historical Park and Lakota Lake are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and Green Mountain National Forest are other places worth a visit.

What’s a holiday rental in Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodstock. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.