
Places to stay in Windsor
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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
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Popular amenities for Windsor places to stay
Stay near Windsor's top sights
Other great vacation rentals in Windsor
Superhost

Cabin in Barnard
4.8 out of 5 average rating, 15 reviewsPrivate post & beam log cabin on Macintosh Pond.
NinaRating, 5 stars4 months ago
It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!
Guest favorite

Home in Bellows falls
5 out of 5 average rating, 9 reviewsAmazing Views, Skiing Nearby and Amenities Galore!
GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Superhost

Home in Manchester
4.86 out of 5 average rating, 35 reviewsYour VT Dream House: Fireplace, Pool, Dogs
AtulRating, 5 stars8 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Guest favorite

Home in Dover
4.91 out of 5 average rating, 11 reviewsAmazing Family getaway!
KerriRating, 5 stars1 month ago
This house was a great spot to stay in between days of skiing. Everything was clean and comfortable.
Top guest favorite

Home in Chittenden
5 out of 5 average rating, 8 reviewsModern Retreat next to Mountain Top Inn,Killington
MaddyRating, 5 stars2 months ago
I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!
Superhost

Cabin in Bridgewater
4.91 out of 5 average rating, 100 reviews100 Acres Views & Creek near Woodstock/Killington
ChristopherRating, 5 stars1 month ago
Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.
Superhost

Home in Tinmouth
4.81 out of 5 average rating, 133 reviewsVermont Lakefront Getaway "The Wild Loon"
WilliamRating, 5 stars2 months ago
The place was perfect for our winter family vacation. The home was as described in a beautiful setting with a great view. If staying in the winter months having a vehicle with at least all wheel drive is helpful, as this is Vermont. The home is out of the way, but easy driving distance to ski and explore the nearby towns.
Guest favorite

Home in Wilmington
4.88 out of 5 average rating, 105 reviewsMtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
JamesRating, 5 stars1 week ago
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
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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- Stratton Mountain
- Squam Lake
- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Owl's Nest Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course
- Baker Hill Golf Club
- Dartmouth Skiway
- Veterans Memorial Recreation Area Ski Hill
- Concord Country Club
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Brattleboro Ski Hill
- Santa's Land USA
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