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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Woodstock holiday homes

A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is £432
includes taxes & fees
4 Oct - 5 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A large house with a fire pit and outdoor seating.

2. 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, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is £436
includes taxes & fees
28 Oct - 29 Oct
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

3. 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 £436
includes taxes & fees
25 Oct - 26 Oct
180-degree panoramic views of Vermont's mountains from the living room and Deck
A modern living room with a fireplace, large windows, and a cozy seating area.

4. Stunning Views, 10 Mins from Woodstock

Stunning Views, 10 Mins from Woodstock
Pomfret
Stunning Views, 10 Mins from Woodstock
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

5. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is £222
includes taxes & fees
28 Oct - 29 Oct
Luxury Condo Tucked in the Heart of Killington
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

6. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is £742
includes taxes & fees
7 Oct - 8 Oct
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A rural landscape with a house surrounded by dense forest, a pond, and a golf course in the distance.

7. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is £353
includes taxes & fees
5 Oct - 6 Oct
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A hot tub surrounded by snow, with lounge chairs and string lights.

8. Fall Getaway Near Killington with Hot Tub

Fall Getaway Near Killington with Hot Tub
Bridgewater
The price is £566
includes taxes & fees
7 Oct - 8 Oct
Fall Getaway Near Killington with Hot Tub
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

9. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is £223
includes taxes & fees
5 Oct - 6 Oct
CozyDen - AC, Bike to Mountain, Porch!
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

10. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is £371
includes taxes & fees
4 Oct - 5 Oct
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

11. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is £178
includes taxes & fees
5 Oct - 6 Oct
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

12. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

13. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is £388
includes taxes & fees
29 Oct - 30 Oct
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

14. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is £527
includes taxes & fees
5 Oct - 6 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

15. Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.

Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Killington
7.6 out of 10, Good, (4 reviews)
"Great location, clean and quiet."
United States
Dr. Stephan B.
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Winter Wonderland

16. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is £522
includes taxes & fees
6 Oct - 7 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

17. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Great amenitiesCleanNewAnd easy access to Starship Gondola at KillingtonWent with my two sons - we had a great time"
United States
Gifford F.
The price is £415
includes taxes & fees
4 Oct - 5 Oct
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
Living area

18. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
10.0 out of 10, Exceptional, (1 review)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
The price is £456
includes taxes & fees
26 Oct - 27 Oct
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
A forested area with a wooden structure and a red and blue playset.

19. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Killington
9.6 out of 10, Exceptional, (72 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is £719
includes taxes & fees
5 Oct - 6 Oct
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A two-story house with a covered porch and a garage.

20. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is £677
includes taxes & fees
4 Oct - 5 Oct
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"My family loved how clean was the room and how nice was the staff."
Regis 1-night trip
Posted 11 hours ago
My Place Hotel-Randolph VT

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
139
Accommodation
871 Holiday Homes
Lowest Price
£178
Highest Price
£742