Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 703 Vacation Homes in Windsor with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar
Enter the home to an open living space

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (94)
"Nice place. we had a great time. "
Beautifully renovated with fireplace and coffee bar
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lake

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (202)
"Great place after a long day of skiing. Very close to Jackson Gore base area. The house was clean and communication was spot on. "
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"The gondola house was perfect for our group. It was spacious and comfortable. Loved having a bathroom on every floor. It was well stocked with everything we could’ve needed. I don’t have one bad thing to say about it. The hot tub was just lovely after a long day of skiing. Would not hesitate to rent this again and highly recommend it."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Elysium on Little Lake Sunapee- Fireplace, Game room, Snowshoe Trail Access
Welcome to Elysium!

Elysium on Little Lake Sunapee- Fireplace, Game room, Snowshoe Trail Access

9.0 out of 10, Wonderful, (2)
"Great living space with a beautiful view of the lake. The beds were comfortable and everything was very clean. Easy ride to Mount Sunapee for a ski day. The kids had a blast playing in the snow in the back yard. The fireplace was great and kept us nice and cozy during the winter storm!"
The price is SAR 1,313
SAR 3,369 total
includes taxes & fees
4 Mar - 5 Mar
Elysium on Little Lake Sunapee- Fireplace, Game room, Snowshoe Trail Access
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Living area

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (91)
"Everything was as advertised! Great location and easy to find. "
The price is SAR 893
SAR 1,735 total
includes taxes & fees
25 Mar - 26 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

9.8 out of 10, Exceptional, (38)
"The property is recently renovated so everything is relatively new and in good condition. The unique design choice of using cedar for the walls, floors and ceiling was a bit off putting initially but we got used to it. There was a small issue with the hot tub, but the host responded very quickly and the issue was resolved the next day. Will definitely consider staying here for the next Okemo ski vacation."
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Vermont's Mountain Villa: Hot tub, Ski views, Pet+

10.0 out of 10, Exceptional, (8)
"I love Winter and love to be in the snow and crisp air. The week was perfect for outside adventures and this home was perfect to warm us and nourish our hearts, bellies and spirits. The views at sunrise and sunset are extrodinary. "
Vermont's Mountain Villa: Hot tub, Ski views, Pet+
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

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

8.0 out of 10, Very Good, (2)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Modern Farm House…minutes to Okemo; 2 King beds!
Interior

Modern Farm House…minutes to Okemo; 2 King beds!

9.4 out of 10, Exceptional, (9)
"We were a few families visiting for a ski weekend. Location was great and the house was clean, updated, and had plenty of space. Only thing we thought was inconvenient was the lack of spare TP! "
Modern Farm House…minutes to Okemo; 2 King beds!
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

10.0 out of 10, Exceptional, (8)
"The Sugar River Treehouse is thoughtfully designed providing all the amenities needed. We thoroughly enjoyed being able to experience a unique setting with our two dogs. We plan on returning in the summer to enjoy the benefits of the Sugar River. "
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Living area flooded with natural light.

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Wonderful home! Excellent layout for family bonding. Hot tub was great. Skiing equipment storage area was Lu fantastic. Easy ski-in ski-out!!! Communication with host was excellent!! Beds were comfy! Would highly recommend! "
The price is SAR 1,762
SAR 3,644 total
includes taxes & fees
5 Mar - 6 Mar
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Townhome with patio & on-site pool, hot tub, sauna & tennis access

Townhome with patio & on-site pool, hot tub, sauna & tennis access

10.0 out of 10, Exceptional, (3)
"Clean and convenient "
Townhome with patio & on-site pool, hot tub, sauna & tennis access
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

9.8 out of 10, Exceptional, (49)
"This is a lovely home -- spacious, beautifully furnished, and well-located, about 15 minutes from Okemo & downtown Ludlow. 4wd recommended for winter visitors: the house is up a steep hill, and in January the road surface was packed-down snow, so it was slippery for cars without all-wheel-drive."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Charming Lakefront Cottage on Lake Mascoma
Moon rise over the lake

Charming Lakefront Cottage on Lake Mascoma

10.0 out of 10, Exceptional, (2)
"Great house. Stylish and comfortable decor. Attention to details was appreciated. Excellent communication with owner. "
The price is SAR 1,050
SAR 2,165 total
includes taxes & fees
24 Feb - 25 Feb
Charming Lakefront Cottage on Lake Mascoma
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"If you're looking for the perfect getaway near Killington, look no further than this incredible rental home! From the moment we stepped inside, we were blown away by how spacious and welcoming the property felt. It easily accommodated our large group, with plenty of room for everyone to relax and enjoy themselves.The home has such a cozy, homey atmosphere that made it hard to leave! We spent our evenings gathered around the real fireplace, which added so much warmth and charm to the experience....
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Killington, Vermont Ski House w/ Hot Tub and Sauna
I Our snow country home welcomes you!

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (84)
"The perfect home to come back to after a day of skiing with a sauna and hot tub to lounge in. So spacious and close to the mountain!"
Killington, Vermont Ski House w/ Hot Tub and Sauna
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Living area

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"The house is beautiful super clean. Plenty of space for our family. The view is amazing. Can’t wait to return in few months! "
The price is SAR 638
SAR 1,689 total
includes taxes & fees
10 Mar - 11 Mar
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Aerial view

Riverfront, family fun, amazing rec room, close to Magic & Okemo

9.8 out of 10, Exceptional, (10)
"We had a great stay here for a quick trip to Okemo, which is about 22 minutes away. House was perfect for our small group and we liked the family room area, although with fresh snow we were all exhausted from skiing and didn’t use it much. The inner breezeway was nice to leave our snow covered and sometimes dirty shoes in which kept the house clean and clear. We would definitely stay here again. Great communication with the host who allowed a late check out. Did at the Scottish pub in Chester...
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.2 out of 10, Wonderful, (66)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is SAR 300
SAR 1,043 total
includes taxes & fees
24 Feb - 25 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

9.2 out of 10, Wonderful, (27)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
The price is SAR 248
SAR 715 total
includes taxes & fees
2 Mar - 3 Mar
Efficient condo near slopes with kitchenette & great location
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.