A snow-covered river valley with a bridge and a town.

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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 Windsor 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 CA $259
CA $602 total
includes taxes & fees
Oct 25 - Oct 26
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is CA $172
CA $639 total
includes taxes & fees
Oct 26 - Oct 27
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
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
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is CA $398
CA $770 total
includes taxes & fees
Oct 26 - Oct 27
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

4. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
The price is CA $170
CA $582 total
includes taxes & fees
Nov 2 - Nov 3
Lakefront Family Fun Retreat
A two-story house with a deck, surrounded by dense forest.

5. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $762
CA $1,429 total
includes taxes & fees
Oct 19 - Oct 20
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A large house with a fire pit and outdoor seating.

6. 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 CA $287
CA $748 total
includes taxes & fees
Nov 1 - Nov 2
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is CA $252
CA $815 total
includes taxes & fees
Oct 19 - Oct 20
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A room with a wooden floor, a sofa, a chair, a small table, a television, and large windows with a view of the outdoors.

8. The Shaker Cottage on Lake Mascoma

The Shaker Cottage on Lake Mascoma
Enfield
The price is CA $282
CA $613 total
includes taxes & fees
Oct 25 - Oct 26
The Shaker Cottage on Lake Mascoma
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

9. 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 CA $130
CA $410 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Condo Tucked in the Heart of Killington
A spacious living room with a fireplace, large windows, and a cozy seating area.

10. @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (27 reviews)
"The perfect winter stay for our family! Perfect location, close to Mount Sunapee. Gorgeous views and home. Host was extremely welcoming and responsive, and the whole stay was easy."
United States
Amanda R.
The price is CA $246
CA $847 total
includes taxes & fees
Nov 17 - Nov 18
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
A stone fire pit with a fire burning in a garden setting.

11. 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 CA $1,273
CA $2,236 total
includes taxes & fees
Oct 19 - Oct 20
Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
A yellow building with a porch and a sign that reads "Brook Road Inn."

12. Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Nice place for a mountain stay"
United States
Meghan B.
The price is CA $240
CA $460 total
includes taxes & fees
Oct 19 - Oct 20
Brook Road Condo
A cozy living room with a fireplace, comfortable seating, and a television.

13. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is CA $256
CA $576 total
includes taxes & fees
Oct 19 - Oct 20
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

14. 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 CA $315
CA $1,004 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

15. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (59 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is CA $277
CA $608 total
includes taxes & fees
Oct 19 - Oct 20
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

16. Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is CA $260
CA $423 total
includes taxes & fees
Oct 19 - Oct 20
Brook Road Condo
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.

17. 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 CA $178
CA $385 total
includes taxes & fees
Oct 21 - Oct 22
CozyDen- Location, Ski Off/ Shuttle On
A two-story house with a covered porch and a garage.

18. 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 CA $298
CA $1,178 total
includes taxes & fees
Oct 19 - Oct 20
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

19. 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 CA $191
CA $697 total
includes taxes & fees
Oct 19 - Oct 20
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A wooden cabin with multiple windows and a balcony, surrounded by trees.

20. Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (32 reviews)
"The Treehouse provided an excellent retreat. Beautiful property and excellent hosts. "
United States
T G.
The price is CA $389
CA $694 total
includes taxes & fees
Nov 2 - Nov 3
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
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 Windsor Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"We visited during the peak of fall colors. Terrific location, up in the mountains, and near several hiking trails. We hiked deer leap overlook trail that went along the AT for a bit then up to a beautiful overlook. Had some great pizza at Gondoughla."
Erik 2-night trip
Posted 3 hours ago
The Mountain Inn at Killington

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
470
Accommodation
833 Vacation Homes
Lowest Price
CA $385
Highest Price
CA $2,236

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