
Beachfront holiday rentals in Windsor County
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Windsor County
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for beachfront rentals in Windsor County
Pet-friendly beachfront home rentals
Top guest favourite

Home in Stockbridge
5 out of 5 average rating, 5 reviewsRiverfront Retreat in Stockbridge
Guest favourite

Home in Cavendish
4.94 out of 5 average rating, 49 reviewsFour Season River Retreat: Private beaches & more!

Cottage in Ludlow
4.81 out of 5 average rating, 37 reviews3BR lakefront with dock, swim platform, & firepit
Guest favourite

Home in Plymouth
4.97 out of 5 average rating, 59 reviewsRenovated Family Lake~Ski House w/ gas fireplace
Private beachfront home rentals
Top guest favourite

Castle in Clarendon
4.98 out of 5 average rating, 477 reviewsKingsley Grist Mill, w/ Private Beach & Waterfall
Guest favourite

Cottage in Acworth
5 out of 5 average rating, 18 reviewsClassic lakeside cottage with gorgeous sunset view

Cottage in Ludlow
4.81 out of 5 average rating, 37 reviews3BR lakefront with dock, swim platform, & firepit

Cabin in Ludlow
4.74 out of 5 average rating, 255 reviewsBeautiful Lake Cabin - Okemo - Great for Famlies
Guest favourite

Cabin in Mount Holly
4.98 out of 5 average rating, 49 reviewsLake House near Ludlow/Okemo and Killington
Guest favourite

Home in Cavendish
4.94 out of 5 average rating, 49 reviewsFour Season River Retreat: Private beaches & more!

Home in Ludlow
4.87 out of 5 average rating, 94 reviewsTranquil Ludlow Waterfront Retreat
Top guest favourite

Home in Stockbridge
5 out of 5 average rating, 5 reviewsRiverfront Retreat in Stockbridge
Destinations to explore
- Tiny house rentals Windsor County
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- Beachfront rentals Vermont
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Fort Ticonderoga
- Tenney Mountain Resort
- Dorset Field Club
- Crotched Mountain Ski and Ride
- Hooper Golf Course
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Cozy Cottages & Otter Valley Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Dartmouth Skiway
- Ekwanok Country Club
- Autumn Mountain Winery
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Mount Sunapee Resort
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Food and drink Vermont
- Nature and outdoors Vermont
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