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Places to stay in Windsor

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for Windsor places to stay

Stay near Windsor's top sights

Harpoon Brewery Taproom and Beer Garden125 locals recommend
Saint-Gaudens National Historical Park62 locals recommend
Windsor Station Restaurant & Barroom33 locals recommend
Brownsville Butcher & Pantry32 locals recommend
Cornish-Windsor Covered Bridge28 locals recommend
Price Chopper27 locals recommend

Other great vacation rentals in Windsor

Superhost
Cabin in Barnard
4.8 out of 5 average rating, 15 reviews

Private 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 reviews

Amazing 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 reviews

Your 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 reviews

Amazing 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 reviews

Modern 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 reviews

100 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 reviews

Vermont 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 reviews

MtSnow * 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Windsor