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Holiday rentals in Windsor

Find and book unique accommodation on Airbnb

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Popular amenities for Windsor holiday rentals

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 holiday rentals in Windsor

Top guest favourite
Home in Thornton
4.99 out of 5 average rating, 68 reviews

70 Acre White Mountain Estate – Panoramic Views

AndreaRating, 5 stars5 days ago
We splurged as a family of 4 w/ our chihuahua. This is the absolute perfect home for 2 or even 3 families. Derek was responsive from day 1 of booking until check-out. The home is gorgeous. It's just as the pictures show, if not better. The basement has a bedroom with 2 Q beds, and the cinema can easily sleep a few more. This was a man cave for our sons! Upstairs, the master bedroom w/bath was perfect. There are 2 bunk beds right next to the master & another bdrm across the house. It's quiet, peaceful, and serene. We walked the trails behind the home (bring boots or hiking shoes if it's been raining). When you pull into the drive, on your right is a rolling river. The hot tub was a huge plus and was relaxing. We loved the fire pit (bring a lighter or matches) and playing pool, air hockey, & shuffleboard. My son brought his xbox & hooked it up to the 85" TV in the cinema. We watched movies via our Netflix account. We hope to go back in the future!
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 favourite
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.
Top guest favourite
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!
Guest favourite
Home in Dover
4.89 out of 5 average rating, 71 reviews

Large Mount Snow Ski House with Hot Tub

AndyRating, 5 stars1 month ago
Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.
Guest favourite
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.
Top guest favourite
Home in Plymouth
5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!

Quick stats about holiday rentals in Windsor

  • Total rentals

    20 properties

  • Nightly prices starting at

    £30 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