Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Winchester
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Top guest favourite
Guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
1–6 Aug
1–6 Aug
$907 SGD
Show price breakdown
for 5 nights
$907 SGD for 5 nights
,
·
4.97 out of 5 average rating, 222 reviews
4.97 (222)
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
New place to stay
New
,
·
6 bedrooms
6 bedrooms
,
·
10 beds
10 beds
,
·
2.5 bathrooms
2.5 bathrooms
9–14 Sept
9–14 Sept
$6,898 SGD
Show price breakdown
for 5 nights
$6,898 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4.94 out of 5 average rating, 36 reviews
4.94 (36)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,674 SGD
Show price breakdown
for 5 nights
$2,674 SGD for 5 nights
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
New place to stay
New
,
·
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
16–21 Aug
16–21 Aug
$7,551 SGD
Show price breakdown
for 5 nights
$7,551 SGD for 5 nights
Free cancellation
Home in Winchester
Highland Lake Guest House | Private Waterfront
New place to stay
New
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$3,098 SGD
Show price breakdown
for 5 nights
$3,098 SGD for 5 nights
Free cancellation
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
·
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
16–21 Aug
16–21 Aug
$8,261 SGD
Show price breakdown
for 5 nights
$8,261 SGD for 5 nights
Superhost
Superhost
Serviced apartment in Winsted
Haven at Highland lake
4.88 out of 5 average rating, 172 reviews
4.88 (172)
,
·
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,336 SGD
$1,175 SGD
Show price breakdown
for 5 nights
Free cancellation
Guest favourite
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
4.91 out of 5 average rating, 65 reviews
4.91 (65)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$2,582 SGD
Show price breakdown
for 5 nights
$2,582 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
4.97 out of 5 average rating, 108 reviews
4.97 (108)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
16–21 Aug
16–21 Aug
$1,724 SGD
Show price breakdown
for 5 nights
$1,724 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
5.0 out of 5 average rating, 6 reviews
5.0 (6)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Aug
1–6 Aug
$9,129 SGD
Show price breakdown
for 5 nights
$9,129 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Tiny home in New Hartford
West Hill Outpost
4.9 out of 5 average rating, 98 reviews
4.9 (98)
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
12–17 Aug
12–17 Aug
$2,003 SGD
Show price breakdown
for 5 nights
$2,003 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
5.0 out of 5 average rating, 17 reviews
5.0 (17)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,581 SGD
Show price breakdown
for 5 nights
$2,581 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Winsted
Newly renovated lakefront home!
4.95 out of 5 average rating, 39 reviews
4.95 (39)
,
·
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$5,290 SGD
$3,915 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Cottage in Winsted
Cottage Ease.
4.93 out of 5 average rating, 54 reviews
4.93 (54)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
8–13 Aug
8–13 Aug
$1,674 SGD
Show price breakdown
for 5 nights
$1,674 SGD for 5 nights
Top guest favourite
Guest favourite
Home in New Hartford
Mountaintop Nirvana: Lake, Hot Tub, Pool Table
4.89 out of 5 average rating, 79 reviews
4.89 (79)
,
·
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$8,483 SGD
Show price breakdown
for 5 nights
$8,483 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Cabin in Colebrook
Rustic Pond Cabin: Nature, Stars & Serenity
4.94 out of 5 average rating, 126 reviews
4.94 (126)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Oct
13–18 Oct
$2,477 SGD
Show price breakdown
for 5 nights
$2,477 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Cabin in Litchfield County
Blackberry Cottage
4.93 out of 5 average rating, 150 reviews
4.93 (150)
,
·
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,472 SGD
Show price breakdown
for 5 nights
$1,472 SGD for 5 nights
Free cancellation
Superhost
Superhost
Home in New Hartford
Sunset Pad. Lakefront for 2, private dock & SUPs.
New place to stay
New
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,490 SGD
Show price breakdown
for 5 nights
$2,490 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
4.99 out of 5 average rating, 246 reviews
4.99 (246)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
16–21 Sept
16–21 Sept
$2,283 SGD
Show price breakdown
for 5 nights
$2,283 SGD for 5 nights
Free cancellation
1
2
3
4
…
15