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Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
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Vacation rentals for every style
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Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor
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Guest favorite
Loft in Shelburne Falls
4.95 out of 5 average rating, 269 reviewsThe Railroad House
![](https://a0.muscache.com/im/pictures/miso/Hosting-45604365/original/5e8adc93-1ca7-4cce-9f01-5d814d03f9c2.jpeg?im_w=720)
Guest favorite
Chalet in Cummington
4.86 out of 5 average rating, 103 reviewsBerkshire A-Frame Chalet!
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Guest favorite
Rental unit in Petersburg
4.86 out of 5 average rating, 154 reviewsThe Beer Diviner Brewery Apartment
![](https://a0.muscache.com/im/pictures/miso/Hosting-50769924/original/cdb63151-b384-48d6-89f1-b3c804204361.jpeg?im_w=720)
Guest favorite
Guesthouse in Williamstown
4.97 out of 5 average rating, 154 reviewsBrookside Cottage
![](https://a0.muscache.com/im/pictures/78b50d2d-4204-4fda-b8b1-e7aaa0c1aa11.jpg?im_w=720)
Guest favorite
Guesthouse in Williamstown
4.93 out of 5 average rating, 220 reviewsPerfect Base for Your Berkshire Adventure
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Guest favorite
Home in New Lebanon
4.99 out of 5 average rating, 351 reviewsThe old sawmill from 1771
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Guest favorite
Guest suite in Charlemont
4.9 out of 5 average rating, 185 reviewsUnique People & Pet-Welcoming Haven
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Guest favorite
Rental unit in North Adams
4.92 out of 5 average rating, 120 reviewsCozy 1 bedroom 1/2 mile to MassMoca
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