
Places to stay in Windsor
Book unique places to stay, houses, and more on Airbnb
Top-rated places to stay in Windsor
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor places to stay
Other great vacation rentals in Windsor
Top guest favorite

Home in Tinmouth
5 out of 5 average rating, 11 reviewsCharming Vermont Schoolhouse

Apartment in Windsor
4.72 out of 5 average rating, 29 reviewsQuaint Vermont Village Apartment 2
Guest favorite

Home in Plainfield
4.85 out of 5 average rating, 108 reviewsThe Oaks - secluded rural estate w/ amazing views
Top guest favorite

Home in West Windsor
5 out of 5 average rating, 15 reviewsElm Gate Farm

Home in Brownsville
4.97 out of 5 average rating, 69 reviewsGorgeous and Secluded Log Home near Woodstock, Vt
Guest favorite

Cabin in Weathersfield
5 out of 5 average rating, 11 reviewsBlack River A-Frame | Fire Pit, Fenced Yard, BBQ
Top guest favorite

Apartment in Springfield
5 out of 5 average rating, 5 reviewsSunny, serene, second floor

Home in Brownsville
4.83 out of 5 average rating, 6 reviewsSkyhawk Cabin: refined modern getaway with hot tub
Quick stats about vacation rentals in Windsor
Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.5K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Self check-in, Gym, and BBQ grill
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- Squam Lake
- Stratton Mountain
- Okemo Mountain Resort
- Weirs Beach
- Monadnock State Park
- Owl's Nest Resort
- Pats Peak Ski Area
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Bretwood Golf Course
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Fox Run Golf Club
- Brattleboro Ski Hill
- Hooper Golf Course
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