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

Search Vacation Homes in Woodstock

Check prices for these dates

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

Our top choices for Woodstock vacation homes

A large house with a fire pit and outdoor seating.

1. 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.
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

2. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
10.0 out of 10, Exceptional, (1 review)
"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...
United States
Melinda D.
Luxury Condo Tucked in the Heart of 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, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
9.2 out of 10, Wonderful, (9 reviews)
"Communication was great! The views from the house were terrific and the living room space is really nice."
United States
Craig K.
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

4. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
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.

5. CozyDen- Fireplace, Ski Off/ Shuttle On

CozyDen- Fireplace, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
CozyDen- Fireplace, Ski Off/ Shuttle On
A red house with a gravel driveway and lush greenery.

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

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

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay but there was some noise in the bigger bedroom from the heating panels so the sleep was disturbed. Other than this, we had a great time at the accommodation."
Canada
Smriti
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A modern kitchen with a dishwasher, a coffee maker, and a dining area with a wooden table set for two.

8. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (18 reviews)
"WE ENJOYED OUR STAY"
United States
Susan E.
Cozy Rutland Retreat
A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

9. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Loved the quiet seclusion of the Shack, but also that we were close to hikes, lakes, markets, and food. We had a wonderful and relaxing stay!!"
United States
Sarah G.
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
An indoor swimming pool with a wooden ceiling and large windows.

10. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
The Woods
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
A kitchen with granite countertops, stainless steel appliances, wooden cabinets, and a large island with seating.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
Slopeside Estate Guesthouse: Hot tub, AC, Grill
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 1 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Killington
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Living area

13. 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
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
A golf course with sand bunkers and a forested area.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A wooden cabin with a circular door, a bench outside, and a view of trees and mountains.

15. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
A spacious living area with a fireplace, a television, and a dining area with natural light.

16. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
A spacious living room with a sofa, coffee table, and fireplace. There is a large window providing a view of the outdoors.

17. 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, (73 reviews)
"Great stay. Killer location!"
United States
Matthew P.
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

18. 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
9.4 out of 10, Exceptional, (8 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.
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A wooden deck with a hot tub, outdoor seating, and a view of a forested hillside.

19. NEW Killington Chalet | Hot Tub, Sauna & Golf Sim

NEW Killington Chalet | Hot Tub, Sauna & Golf Sim
Killington
NEW Killington Chalet | Hot Tub, Sauna & Golf Sim
A house with a covered deck, a barbecue grill, and a wooden pergola.

20. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (10 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
large ski ranch hot tub close to killington pets ok
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
"Room was great, fireplace was great touch. Will stay again next time we are in the area."
Dennis 1-night trip
Posted 3 hours ago
Fireside Inn & Suites West Lebanon

Find out more about Woodstock

Woodstock Vacation Homes information

Number of reviews
126
Accommodation
898 Vacation Homes
Lowest Price
Highest Price

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