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

Search Vacation Homes in Woodstock

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Woodstock vacation homes

A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

1. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
Hartford
10.0 out of 10, Exceptional, (179 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
The price is ￥28,918
￥67,676 total
includes taxes & fees
Oct 25 - Oct 26
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
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, (3 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 ￥33,816
￥85,836 total
includes taxes & fees
Oct 29 - Oct 30
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

3. 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.
The price is ￥14,538
￥45,799 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Condo Tucked in the Heart of Killington
A stone fire pit with a fire burning in a garden setting.

4. Spacious home on picturesque grounds with stunning views. Quechee - Woodstock

Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
Hartford
10.0 out of 10, Exceptional, (92 reviews)
"Excellent communication and gorgeous area"
United States
Lauren R.
The price is ￥142,218
￥249,809 total
includes taxes & fees
Oct 19 - Oct 20
Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is ￥28,181
￥90,028 total
includes taxes & fees
Oct 18 - Oct 19
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

6. 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.
The price is ￥35,227
￥111,254 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
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, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is ￥45,194
￥86,425 total
includes taxes & fees
Oct 26 - Oct 27
180-degree panoramic views of Vermont's mountains from the Living room, 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.

8. CozyDen- Location, Ski Off/ Shuttle On

CozyDen- Location, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is ￥19,911
￥43,034 total
includes taxes & fees
Oct 21 - Oct 22
CozyDen- Location, Ski Off/ Shuttle On
A cozy living room with a fireplace, a television, and a view of a snowy deck.

9. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is ￥29,515
￥114,884 total
includes taxes & fees
Oct 18 - Oct 19
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is ￥29,695
￥160,172 total
includes taxes & fees
Oct 20 - Oct 21
Slopeside Estate Guesthouse: Hot tub, AC, Grill
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.

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
10.0 out of 10, Exceptional, (1 review)
"The only struggle was we got on late at night. We couldn’t find the driveway and then it said the lower, condo we did not realize we had to go downstairs. But once found it everything was great. It was a fully functioning kitchen, towels, soaps, clean and even a working grill with a beautiful view to sit on the porch. We would rent again!"
United States
Annette G.
The price is ￥29,515
￥78,636 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A forested area with a wooden structure and a red and blue playset.

12. 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 ￥27,611
￥120,347 total
includes taxes & fees
Oct 18 - Oct 19
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A bedroom with a large bed, a sofa, a desk, and two windows.

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

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
The Woods
The price is ￥22,015
￥56,125 total
includes taxes & fees
Nov 1 - Nov 2
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

14. 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 ￥14,080
￥36,623 total
includes taxes & fees
Nov 1 - Nov 2
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Living area

15. 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 ￥51,028
￥96,945 total
includes taxes & fees
Oct 26 - Oct 27
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is ￥19,247
￥71,367 total
includes taxes & fees
Oct 26 - Oct 27
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
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 Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A cabin with a deck, a hot tub, and a fire pit area.

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

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
The price is ￥54,507
￥116,639 total
includes taxes & fees
Oct 28 - Oct 29
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
A kitchen with wooden cabinets, a white refrigerator, a microwave, a stove, and a toaster.

19. Liquid Lodge Upper: 4BR Duplex with Hot Tub and 1 PM Checkout

Liquid Lodge Upper: 4BR Duplex with Hot Tub and 1 PM Checkout
Killington
Liquid Lodge Upper: 4BR Duplex with Hot Tub and 1 PM Checkout
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

20. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is ￥31,038
￥100,764 total
includes taxes & fees
Oct 18 - Oct 19
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodstock Hotel Reviews

Lincoln Inn & Gallery

Lincoln Inn & Gallery

10/10 Excellent
"Lovely place just a few miles (10 minutes) outside of the town center, and very accessible to everything we wanted to do. The grounds were beautiful and relaxing. We drove into town center several times but we were glad we stayed away from the crowds. There's a wonderful Farmer's Market super close, so our last night, we ate in with the food we purchased there. Full refrigerator, microwave and all the comforts of home. Not a huge room, but so well organized that I worked great for the two of us. Would stay here again. Nice hosts!"
Sheryl 4-night trip
Posted 5 hours ago
Lincoln Inn & Gallery

Find out more about Woodstock

Woodstock Vacation Homes information

Number of reviews
431
Accommodation
898 Vacation Homes
Lowest Price
￥36,623
Highest Price
￥249,809