Photo by William E Berry Jr.

Search Vacation Homes in Windsor

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 856 Vacation Homes in Windsor with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (99)
"Our stay was terrific! Such a lovely renovated home! "
Beautifully renovated with fireplace and coffee bar

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

10.0 out of 10, Exceptional, (2)
"The property was perfect for a Vermont getaway that will allow you to enjoy the autumn views and still give you the opportunity to engage in plenty of activities if you desire. Highly recommend this home!!"
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Saltbox townhome with AC, fireplace & deck - near Quechee Club, golf & ski

9.2 out of 10, Wonderful, (15)
"Place was nice and 20 min drive to Dartmouth door to door. Everything you need and plenty of space. Only glitch was the battery on door code died after coming home from dinner. However, we called service # on our confirm and they provided us a lockbox code for a key in less than 5 min so not an issue. "
Saltbox townhome with AC, fireplace & deck - near Quechee Club, golf & ski

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

9.8 out of 10, Exceptional, (21)
"House is 1 minute or less from the Skye Peak Gondola, which as convenient for skiing. Clean house, has lots of room and games for families. Hot tub was really nice too."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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

9.0 out of 10, Wonderful, (4)
"We had a great time during our stay. The house was cozy and clean and had more than enough beds for us 12. Did some ice fishing, hit the golf simulator in Lebanon and had an overall great stay"
The price is SAR 1,313
SAR 3,362 total
includes taxes & fees
23 Mar - 24 Mar
Elysium on Little Lake Sunapee- Fireplace, Game room, Snowshoe Trail Access

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

9.4 out of 10, Exceptional, (42)
"Lovely, clean property in beautiful setting. Cozy little escape! So close to amazing trails and hikes. Gorgeous setting. We have family in QueChee and it was perfectly located and so nice to have our own space! Would love to stay there again!"
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (170)
"Three families spent a week at this beautiful log cabin. Seriosluy, the pictures dont do it justice. The home has plenty of space. The rooms were huge. it had plenty of bathrooms. It was well-appointed and well-maintained. There was a ton of available firewood for our use, which we took advantage of. Radiant heat floors were magical when the temps were below zero. Heather, the host was easy to communicate with and answered any and all questions promptly. We had a lot of snow before and during...
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

10.0 out of 10, Exceptional, (16)
"We came to stay as a group of 6 adults and 3 children for a weekend of skiing and thoroughly enjoyed our home away from home for the weekend. The house was spacious but cozy, and well equipped with everything we needed! The house just minutes from Mt Sunapee, Our only complaint is that the downstairs bedroom got quite hot, and that the boiler pipes were a bit noisy if downstairs. We would definitely stay here again though - the kids loved it."
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (23)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.6 out of 10, Exceptional, (119)
"The house was great for our large gathering of multiple families with kids. The commercial range with griddle was awesome and made cooking for the group so much easier. The house had multiple living spaces so it allowed a few in the group that had to work during the week to find a nice space away from the main group. Proximity to Killington was great!We were there during the Presidents Day holiday week so our check in got delayed (5pm) and check out was a bit early (10am), but totally...
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (35)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (69)
"House was perfectly suited to a large group. Minutes walk from the bars and a very short journey to the mountain. Would definitely stay again."
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

9.0 out of 10, Wonderful, (4)
"Great value and location to Okemo. Place was comfortable and clean and to our surprise there was a refrigerator that wasn’t noted in the listing that came in very handy. Would stay again."
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

Ski Chalet-Style Home with Hot Tub Spa, Eastman Community

10.0 out of 10, Exceptional, (28)
"Very comfy with all the conveniences of home…plus a rec area with pool table!!! Beautiful scenery and location was great as it was within short distance from several other towns, restaurants & stores to explore. Home was one of the cleanest we’ve ever stayed in and the owner was a delight. Very friendly, helpful & really cared. Looking forward to coming back!"
Ski Chalet-Style Home with Hot Tub Spa, Eastman Community

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

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

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (35)
"Property was super clean and SO CLOSE to the mountain. Everything was perfect- no complaints! "
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (27)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging

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

9.8 out of 10, Exceptional, (205)
"If your looking for beauty nature and comfort this cozy cottage surpassed our expectations our dog loved the lake and ducks and snow we lived ludlow okemo woodstock and Westin all so close great location and our host was wonderful prompt response with any questions and added a night last minute for us thanks so much Kristin "
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

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

9.6 out of 10, Exceptional, (37)
"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
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windsor

Mountain Green

2.0 star property
5.8 out of 10, (8)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is SAR 807
SAR 1,082 total
includes taxes & fees
3 Apr - 4 Apr
Mountain Green

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

9.0 out of 10, Wonderful, (70)
"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 1,004 total
includes taxes & fees
3 Apr - 4 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.