Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favorite
Home in Athens
5 out of 5 average rating, 35 reviewsPerfect home for a getaway from NYC
Guest favorite
Home in Hillsdale
5 out of 5 average rating, 50 reviewsLakefront close to ski & shopping
Guest favorite
Home in Millerton
4.97 out of 5 average rating, 155 reviewsVacation Home In Millerton
Guest favorite
Chalet in Athens
4.84 out of 5 average rating, 45 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
Guest favorite
Cabin in Cornwall
5 out of 5 average rating, 35 reviewsBeautiful Cabin in Cornwall CT.
Guest suite in Goshen
4.72 out of 5 average rating, 242 reviewsRural Litchfield County Apartment Goshen CT
Guest favorite
Home in Canaan
5 out of 5 average rating, 11 reviewsLuxury/pool/private Villa Mariana Blackberry River
Guest favorite
Home in Bethlehem
5 out of 5 average rating, 35 reviewsLakeview Expanse
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