Photo by William E Berry Jr.

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

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (94)
"My family and I loved staying at this cozy condo in Quechee. It really had everything we needed and more. The location is perfect for exploring downtown and traveling to nearby towns. We loved having the fireplace and used it every night! Vermont received a lot of snow while we were visiting, and the owners really took care of us. The whole complex was plowed nicely, and overall we were really impressed by their thoughtfullness and attention. Would definitely stay here again!"
Beautifully renovated with fireplace and coffee bar

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

9.8 out of 10, Exceptional, (202)
"Beautiful cozy cottage, but the road is a little loud. The creek and backyard are gorgeous."
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

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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

10.0 out of 10, Exceptional, (1)
"Perfect! We absolutely loved the light filled living area overlooking the lake. The fireplace and swing chair were favorites. The hosts were very generous in providing firewood and use of the lockable garage to store our ice fishing gear at night. We enjoyed big family dinners & breakfasts gathered around the large high top seating area with ice fishing, skating and sledding in between. The big, comfy couch was perfect for conversations around the crackling fire while the younger kids had a...
The price is AED 1,286
AED 3,300 total
includes taxes & fees
3 Mar - 4 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

9.8 out of 10, Exceptional, (91)
"Great location in town and close to shuttle. Able to walk to restaurants. Host very responsive and answered quickly. Comfortable beds. Great for 5 adults. Easily fit 3 cars in driveway."
The price is AED 837
AED 1,654 total
includes taxes & fees
4 Mar - 5 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

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+

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.

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!

9.4 out of 10, Exceptional, (9)
"It is the perfect house for two families to stay in for a ski weekend. There are plenty of arcade and board games to entertain the teens. We will be back!"
Modern Farm House…minutes to Okemo; 2 King beds!

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)

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! "
BruinsDen - Ski On Ski Off (Home Stretch Trail)

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

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

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

10.0 out of 10, Exceptional, (1)
"We found this place to be absolutely beautiful with a great view of lake. The home was very clean and spacious. The host stocked the bathrooms and kitchen with everything you could possibly need. We found the beds to be very comfortable. The office/play room had plenty of toy’s for our grand son.The use of the pellet stove made very cozy. We look forward to another visit."
Charming Lakefront Cottage on Lake Mascoma

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

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

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 AED 624
AED 1,654 total
includes taxes & fees
3 Mar - 4 Mar
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

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
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

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 AED 253
AED 714 total
includes taxes & fees
25 Feb - 26 Feb
Efficient condo near slopes with kitchenette & great location

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

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (65)
"Perfect for a quick ski trip for 2 of us. Clean and comfortable and walkable to the spots in town. We will be back! "
The price is AED 496
AED 1,090 total
includes taxes & fees
12 Mar - 13 Mar
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
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.