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

Holiday Homes in Woodstock

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Check prices for these dates

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

Our top choices for Woodstock holiday 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 €383
includes taxes & fees
25 Oct - 26 Oct
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

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.
The price is €262
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo Tucked in the Heart of Killington
A large house with a fire pit and outdoor seating.

3. 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 €486
includes taxes & fees
3 Nov - 4 Nov
Pet Friendly | Game Room | Minutes to Woodstock and Killington
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.

4. 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 €247
includes taxes & fees
21 Oct - 22 Oct
CozyDen- Location, Ski Off/ Shuttle On
A stone fire pit with a fire burning in a garden setting.

5. 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 €1,403
includes taxes & fees
19 Oct - 20 Oct
Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
A compact kitchen with a refrigerator, stove, microwave, and sink.

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 cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

7. 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 room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

8. 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 €481
includes taxes & fees
26 Oct - 27 Oct
180-degree panoramic views of Vermont's mountains from the living room and Deck
A bedroom with a large bed, a sofa, a desk, and two windows.

9. 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 €324
includes taxes & fees
15 Nov - 16 Nov
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.

10. 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 €212
includes taxes & fees
1 Nov - 2 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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 €446
includes taxes & fees
18 Oct - 19 Oct
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is €911
includes taxes & fees
19 Oct - 20 Oct
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A cozy living room with a fireplace, a television, and a view of a snowy deck.

13. 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 €649
includes taxes & fees
18 Oct - 19 Oct
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A forested area with a wooden structure and a red and blue playset.

14. 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.
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is €407
includes taxes & fees
28 Oct - 29 Oct
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

16. 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.
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
A dining table set with plates, glasses, and a vase with a plant.

17. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is €172
includes taxes & fees
20 Oct - 21 Oct
Cozy Rutland Retreat
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 €550
includes taxes & fees
26 Oct - 27 Oct
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
A cabin with a deck, a hot tub, and a fire pit area.

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

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
The price is €657
includes taxes & fees
28 Oct - 29 Oct
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

20. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"We loved our stay! Mike was an amazing host and breakfast was delicious every morning. The lodge had everything you could ask for and more! Truly a gem."
Kolton 2-night trip
Posted 1 hour ago
Mountain Meadows Lodge

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
447
Accommodation
869 Holiday Homes
Lowest Price
€172
Highest Price
€1,403