filters

Search results; Over 1,000 homes in Winchester

Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 private bathroom
26–31 Jul
,
4.97 out of 5 average rating, 219 reviews
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
18–23 Jul
4.95 out of 5 average rating, 39 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
20–25 Jul
4.91 out of 5 average rating, 65 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
20–25 Jul
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.99 out of 5 average rating, 246 reviews
Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 171 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
2 bedrooms, 4 beds, 1 bathroom
2–7 Oct
4.99 out of 5 average rating, 115 reviews
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
4.93 out of 5 average rating, 145 reviews
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 107 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 59 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.88 out of 5 average rating, 128 reviews
Guest favourite
Cottage in Barkhamsted
Cottage - 2 bdr - West Hill Lake w/ Private Beach
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Guest house in Litchfield
The Cottage @ 228 Maple
3 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
5.0 out of 5 average rating, 36 reviews
Guest favourite
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
3–8 Aug
4.86 out of 5 average rating, 14 reviews
Top guest favourite
Guest house in Barkhamsted
Farmington River Carriage House Pleasant Valley CT
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.91 out of 5 average rating, 119 reviews