A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Woodstock vacation 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, (14 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 ￥17,662
￥27,801 total
includes taxes & fees
Nov 3 - Nov 4
Fat Sheep Farm & Cabins
A bedroom with a colorful tapestry featuring ice cream and desserts, a bed with white linens, a black and white patterned pillow, and a bedside lamp.

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 ￥15,687
￥32,152 total
includes taxes & fees
Nov 4 - Nov 5
Bridgewater Living - Ben&Jerry Suite
A sunroom with wicker furniture, large windows, and string lights.

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is ￥17,334
￥32,530 total
includes taxes & fees
Oct 27 - Oct 28
Addie's Place: A Quiet and Quirky Guesthouse
A large house with a fire pit and outdoor seating.

4. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is ￥15,687
￥32,152 total
includes taxes & fees
Nov 1 - Nov 2
Bridgewater Living - Ski VT Suite
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 ￥31,374
￥82,401 total
includes taxes & fees
Oct 26 - Oct 27
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

6. 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 ￥11,910
￥40,330 total
includes taxes & fees
Oct 26 - Oct 27
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.

7. 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.
The price is ￥18,903
￥57,877 total
includes taxes & fees
Oct 26 - Oct 27
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Aerial view

8. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is ￥35,649
￥73,726 total
includes taxes & fees
Oct 28 - Oct 29
The Suites at Killington Center
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

9. 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, (72 reviews)
"This condo is in a great location and offers plenty of space with 2 full bathrooms. It is ground floor with no steps to get in. Beds were comfortable and plenty of towels were provided. We came in summer and the unit does have two AC units in it. The description and photos are accurate, and it was a very pleasant stay."
United States
Mari B.
The price is ￥20,793
￥61,074 total
includes taxes & fees
Oct 26 - Oct 27
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

10. 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 ￥15,122
￥44,855 total
includes taxes & fees
Oct 26 - Oct 27
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

11. 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 ￥18,715
￥58,300 total
includes taxes & fees
Oct 26 - Oct 27
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
A modern bedroom with a bed, bedside table, and a window with a view.

12. 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 ￥12,098
￥40,564 total
includes taxes & fees
Oct 26 - Oct 27
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

13. 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 ￥11,530
￥45,456 total
includes taxes & fees
Oct 26 - Oct 27
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.

14. 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, (14 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 ￥17,202
￥50,278 total
includes taxes & fees
Oct 26 - Oct 27
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

15. 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)
"We had a fantastic stay for a long weekend away. The house is unique and cozy, and very close to any dining amenities and outdoor activities you’re looking for. We will definitely stay here again!"
United States
John D.
The price is ￥22,683
￥75,857 total
includes taxes & fees
Oct 26 - Oct 27
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
A living room with a fireplace, a sofa, a coffee table, and a television.

16. Mountain Green high-floor front condo in Building 3 with ski trail views

Mountain Green high-floor front condo in Building 3 with ski trail views
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is ￥14,660
￥59,573 total
includes taxes & fees
Oct 26 - Oct 27
Mountain Green high-floor front condo in Building 3 with ski trail views
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

17. 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 ￥23,629
￥64,906 total
includes taxes & fees
Oct 26 - Oct 27
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

18. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is ￥18,903
￥58,696 total
includes taxes & fees
Oct 26 - Oct 27
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A modern wooden cabin with a deck, large windows, and a view of the forest.

19. 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 ￥46,590
￥139,683 total
includes taxes & fees
Oct 28 - Oct 29
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Room

20. Cozy Hotel Room Style Studio Condo With Pool

Cozy Hotel Room Style Studio Condo With Pool
3.0 star property
Killington
The price is ￥18,455
￥38,421 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Hotel Room Style Studio Condo With Pool
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

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"Great stay clean and neat!"
Mark 2-night trip
Posted 4 hours ago
Fireside Inn & Suites West Lebanon

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 vacation rentals in Woodstock?

Yes, we offer vacation rentals in Woodstock close to Billings Farm and Museum, or you can choose a more remote option if you want a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your vacation.

What's the top vacation rental that Woodstock has to offer?

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town: This highly rated vacation home rental in Woodstock is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection 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 vacation rentals are there in Woodstock?

Expedia has 37 vacation 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 vacation rental in Woodstock like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Woodstock. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.