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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Woodstock vacation rentals

1. Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway

Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
Woodstock
The price is ￥50,198
￥83,530 total
includes taxes & fees
Sep 3 - Sep 4
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

2. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is ￥30,980
￥42,453 total
includes taxes & fees
Sep 1 - Sep 2
Fat Sheep Farm & Cabins

3. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is ￥19,123
￥36,767 total
includes taxes & fees
Aug 30 - Aug 31
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
9.4 out of 10, Exceptional, (16 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is ￥23,904
￥41,238 total
includes taxes & fees
Sep 7 - Sep 8
Addie's Place: A Quiet and Quirky Guesthouse

5. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is ￥19,123
￥36,946 total
includes taxes & fees
Aug 30 - Aug 31
Bridgewater Living - Ben&Jerry Suite
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

6. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is ￥11,940
￥36,469 total
includes taxes & fees
Sep 1 - Sep 2
Mountain Green
A wooden deck with a covered seating area, a grill, and string lights.

7. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (13 reviews)
"Such a beautiful home and property! Our host was amazing! I would recommend this property to anyone! Thank you! We loved our stay!"
United States
Meg K.
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

8. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (53 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
The price is ￥26,964
￥58,662 total
includes taxes & fees
Aug 31 - Sep 1
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
A compact living space with a dining area, kitchen, and a sofa.

9. 103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (19 reviews)
"Would stay again!"
United States
Hannah M.
The price is ￥16,565
￥25,084 total
includes taxes & fees
Aug 30 - Aug 31
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
An outdoor patio with a sofa, a patterned rug, and a lamp.

10. Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.

Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I would highly recommend a stay at this cozy Mt Green Condo. It was clean, spacious, had everything we needed, and was only a five minute shuttle ride to the mountain. The indoor pool and hot tub in the building were great to come back to after a full day of skiing. Thank you to Dave and the Simple Vacations Rental Team for a great few days away!"
United States
Erin M.
The price is ￥17,667
￥59,999 total
includes taxes & fees
Aug 31 - Sep 1
Cozy 1BR/1BA Mt Green Condo with Amenities and Discounted Ski Rentals. Shuttle.
A cozy living room with a brick fireplace, two sofas, a coffee table, and a TV mounted on the wall.

11. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is ￥17,928
￥54,115 total
includes taxes & fees
Aug 30 - Aug 31
Killington condo 5 min to killington resort
A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

12. 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, (21 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is ￥23,043
￥77,061 total
includes taxes & fees
Sep 3 - Sep 4
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

13. 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, (8 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 ￥13,058
￥42,340 total
includes taxes & fees
Sep 1 - Sep 2
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A residential area with houses, a swimming pool, and a mountain backdrop.

14. 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, (4 reviews)
"Place was great"
United States
Nathan H.
The price is ￥12,290
￥41,207 total
includes taxes & fees
Sep 2 - Sep 3
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A wooden cabin with multiple balconies and a stone chimney.

15. Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (58 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
The price is ￥33,096
￥94,102 total
includes taxes & fees
Aug 31 - Sep 1
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
A living room with a fireplace, a sofa, a coffee table, and a television.

16. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is ￥14,892
￥60,518 total
includes taxes & fees
Aug 31 - Sep 1
Resort condo with mountain views, full kitchen, and free WiFi
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

17. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is ￥8,199
￥36,987 total
includes taxes & fees
Sep 1 - Sep 2
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A spacious restaurant with high ceilings, exposed ductwork, and a mix of wooden and metal furniture.

18. Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is ￥17,318
￥55,405 total
includes taxes & fees
Sep 1 - Sep 2
Killington resort: Walk to Mountain, Biking & Pool
An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

19. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
8.0 out of 10, Very Good, (1 review)
The price is ￥10,370
￥38,462 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
A view of a grassy area with a ski lift and a building in the background.

20. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is ￥11,880
￥42,429 total
includes taxes & fees
Aug 30 - Aug 31
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"We have stayed several times over the years. The property is always well maintained and the Staff is excellent. Greatclocation"
Vickie 3-night trip
Posted 5 hours ago
Align Inn Vermont

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: Visitors give good reviews to this Woodstock vacation home rental, which 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.

How many vacation rentals are there in Woodstock?

Expedia has 36 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 Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and Red Wagon Toy Company 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.