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

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is HK$1,684
HK$2,263 total
includes taxes & fees
22 Oct - 23 Oct
Fat Sheep Farm & Cabins
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is HK$1,106
HK$1,950 total
includes taxes & fees
29 Sept - 30 Sept
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, (18 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$824
HK$1,551 total
includes taxes & fees
28 Sept - 29 Sept
Addie's Place: A Quiet and Quirky Guesthouse
A compact kitchen with a refrigerator, stove, microwave, and sink.

4. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is HK$1,399
HK$4,241 total
includes taxes & fees
28 Sept - 29 Sept
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

5. Gorgeous, clean studio in brand new building.

Gorgeous, clean studio in brand new building.
Hartford
The price is HK$981
HK$1,595 total
includes taxes & fees
28 Sept - 29 Sept
Gorgeous, clean studio in brand new building.
A bedroom with two beds, a door, and a small table with a lamp.

6. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is HK$1,106
HK$1,942 total
includes taxes & fees
29 Sept - 30 Sept
Bridgewater Living - Ski VT Suite
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

7. 180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is HK$2,209
HK$3,985 total
includes taxes & fees
28 Sept - 29 Sept
180-degree panoramic views of Vermont's mountains from the living room and Deck
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

8. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
The price is HK$577
HK$2,167 total
includes taxes & fees
28 Sept - 29 Sept
Welcoming condo near the slopes with free WiFi and full kitchen
A residential area with houses, a swimming pool, and a mountain backdrop.

9. 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 HK$633
HK$1,984 total
includes taxes & fees
28 Sept - 29 Sept
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A living room with a fireplace, a sofa, a coffee table, and a television.

10. 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 HK$733
HK$2,819 total
includes taxes & fees
28 Sept - 29 Sept
Resort condo with mountain views, full kitchen, and free WiFi
A wooden cabin with multiple balconies and a stone chimney.

11. 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
9.2 out of 10, Wonderful, (59 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 HK$1,922
HK$4,698 total
includes taxes & fees
30 Sept - 1 Oct
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

12. 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.
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

13. 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)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is HK$662
HK$2,019 total
includes taxes & fees
28 Sept - 29 Sept
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

14. 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 HK$1,040
HK$2,885 total
includes taxes & fees
28 Sept - 29 Sept
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

15. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (54 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is HK$1,937
HK$3,455 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

16. Clean, cozy, beautiful studio in the heart of WRJ.

Clean, cozy, beautiful studio in the heart of WRJ.
Hartford
Clean, cozy, beautiful studio in the heart of WRJ.

17. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is HK$1,224
HK$3,072 total
includes taxes & fees
12 Oct - 13 Oct
The Suites at Killington Center
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

18. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

19. 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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is HK$404
HK$1,767 total
includes taxes & fees
28 Sept - 29 Sept
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

20. 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 HK$1,352
HK$3,036 total
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
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

The Jackson

The Jackson

10/10 Excellent
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted 2 hours ago
The Jackson

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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  • 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 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 36 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.