Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
Home in Colebrook
4.99 out of 5 average rating, 200 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.
24–31 Oct
Flat in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
14–21 Sep
Guest suite in Bethlehem
4.99 out of 5 average rating, 193 reviewsBreezy Crest private & restful w/antique charm
Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.
20–27 Apr
Holiday rentals for every style
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Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Cottage in Collinsville
4.96 out of 5 average rating, 110 reviewsThe Carriage House
3–10 Sep
Flat in Simsbury
4.98 out of 5 average rating, 231 reviewsEnsign House Room
17–24 Feb
Home in Southwick
4.99 out of 5 average rating, 177 reviewsLinny's Lakeview Cottage
19–26 Nov
Flat in Litchfield
4.98 out of 5 average rating, 118 reviewsLitchfield Hills Hideaway
20–27 Jan
Flat in Brookfield
4.94 out of 5 average rating, 179 reviewsPeaceful apartment on 3.5 acres w/ Artist studio.
3–10 Mar
Serviced apartment in Winsted
4.85 out of 5 average rating, 60 reviewsHaven at Highland lake
16–23 Aug
Flat in Winsted
4.94 out of 5 average rating, 34 reviewsGetaway for a weekend! Close to Ski Sundown.
1–8 Oct
Guest suite in Winchester
4.94 out of 5 average rating, 51 reviewsPrivate Suite 2 Bedroom Deck Lake Views
17–24 Apr
Guest house in New Hartford
4.86 out of 5 average rating, 79 reviewsLitchfields West Hill New Hartford Four Season BNB
6–13 Jan
Flat in Winsted
4.87 out of 5 average rating, 30 reviews1st Floor The Inn at Highland Lake
8–15 Mar
Home in Winchester
4.87 out of 5 average rating, 23 reviewsWinchester House with wifi/high speed internet.
15–22 Sep
Home in Winsted
5.0 out of 5 average rating, 28 reviewsLake House- Great for Families
26 Dec – 2 Jan
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