
Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor
Guest favourite

Private room in Hartland
4.93 out of 5 average rating, 224 reviews"Good Night Moon Vintage" El Rey Glamping
Guest favourite

Private room in Newport
4.85 out of 5 average rating, 62 reviewsComfy Newport stay (White room)
Guest favourite

Private room in Windsor
4.93 out of 5 average rating, 371 reviewsWeaving Dreams Farm and Boutique
Superhost

Private room in West Windsor
4.85 out of 5 average rating, 94 reviewsThorny Hills Farm
Guest favourite

Private room in Cornish
4.91 out of 5 average rating, 159 reviewsFitch Family Farm
Guest favourite

Shared room in Woodstock
4.83 out of 5 average rating, 35 reviewsA Bunk at Wise Pines
Top guest favourite

Private room in Cavendish
4.97 out of 5 average rating, 36 reviewsYakPod #1 Snowed Inn Pod Lodge Leafpeepers Welcome
Top guest favourite

Private room in Hartland
4.98 out of 5 average rating, 273 reviewsSpooner House - Gates Room with Private Bath
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Philadelphia Holiday rentals
- Jersey Shore Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Squam Lake
- Stratton Mountain
- Okemo Mountain Resort
- Weirs Beach
- Owl's Nest Resort
- Monadnock State Park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Brattleboro Ski Hill
- Ekwanok Country Club
- Fox Run Golf Club