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.

Guest favourite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook 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

$309 SGD per night
Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern 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

$144 SGD per night
Guest favourite

Guest suite in Bethlehem

4.99 out of 5 average rating, 193 reviews

Breezy 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

$163 SGD per night

Popular amenities for Winchester holiday rentals

Stay near Winchester's top sights

Kent Pizza4 locals recommend
Mario's Tuscany Grill11 locals recommend
Stop & Shop8 locals recommend
R&B Sports World3 locals recommend
Little Red Barn Brewers5 locals recommend
Gilson Cinema & Cafe14 locals recommend

Other great holiday rentals in Winchester

Guest favourite

Cottage in Collinsville

4.96 out of 5 average rating, 110 reviews

The Carriage House

3–10 Sep

$227 SGD per night
Guest favourite

Flat in Simsbury

4.98 out of 5 average rating, 231 reviews

Ensign House Room

17–24 Feb

$235 SGD per night
Guest favourite

Home in Southwick

4.99 out of 5 average rating, 177 reviews

Linny's Lakeview Cottage

19–26 Nov

$188 SGD per night
Guest favourite

Flat in Litchfield

4.98 out of 5 average rating, 118 reviews

Litchfield Hills Hideaway

20–27 Jan

$186 SGD per night
Guest favourite

Flat in Brookfield

4.94 out of 5 average rating, 179 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

3–10 Mar

$162 SGD per night
Superhost

Serviced apartment in Winsted

4.85 out of 5 average rating, 60 reviews

Haven at Highland lake

16–23 Aug

$121 SGD per night
Guest favourite

Flat in Winsted

4.94 out of 5 average rating, 34 reviews

Getaway for a weekend! Close to Ski Sundown.

1–8 Oct

$145 SGD per night
Guest favourite

Guest suite in Winchester

4.94 out of 5 average rating, 51 reviews

Private Suite 2 Bedroom Deck Lake Views

17–24 Apr

$148 SGD per night
Guest favourite

Guest house in New Hartford

4.86 out of 5 average rating, 79 reviews

Litchfields West Hill New Hartford Four Season BNB

6–13 Jan

$137 SGD per night
Superhost

Flat in Winsted

4.87 out of 5 average rating, 30 reviews

1st Floor The Inn at Highland Lake

8–15 Mar

$272 SGD per night
Guest favourite

Home in Winchester

4.87 out of 5 average rating, 23 reviews

Winchester House with wifi/high speed internet.

15–22 Sep

$252 SGD per night
Guest favourite

Home in Winsted

5.0 out of 5 average rating, 28 reviews

Lake House- Great for Families

26 Dec – 2 Jan

$772 SGD per night

Destinations to explore