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
Filters
0
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
Show map
Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Guest favourite
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom
,
·
5 beds
,
·
1 private bathroom
31 Aug – 5 Sept
31 Aug – 5 Sept
$823 SGD
Show price breakdown
for 5 nights
$823 SGD for 5 nights
,
·
4.9 out of 5 average rating, 421 reviews
4.9 (421)
Top guest favourite
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
$2,554 SGD
Show price breakdown
for 5 nights
$2,554 SGD for 5 nights
4.94 out of 5 average rating, 32 reviews
4.94 (32)
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
7–12 Jul
7–12 Jul
$8,274 SGD
Show price breakdown
for 5 nights
$8,274 SGD for 5 nights
Guest favourite
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
5–10 Jul
5–10 Jul
$2,586 SGD
Show price breakdown
for 5 nights
$2,586 SGD for 5 nights
4.91 out of 5 average rating, 65 reviews
4.91 (65)
Top guest favourite
Guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
18–23 Jul
18–23 Jul
$5,265 SGD
$3,921 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 38 reviews
4.95 (38)
Top guest favourite
Guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
11–16 Jul
11–16 Jul
$934 SGD
Show price breakdown
for 5 nights
$934 SGD for 5 nights
4.97 out of 5 average rating, 213 reviews
4.97 (213)
Guest favourite
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,585 SGD
Show price breakdown
for 5 nights
$2,585 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Guest favourite
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
3 bedrooms
3 bedrooms
,
·
8 beds
8 beds
22–27 Aug
22–27 Aug
$2,743 SGD
Show price breakdown
for 5 nights
$2,743 SGD for 5 nights
4.97 out of 5 average rating, 75 reviews
4.97 (75)
Guest favourite
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
1–6 Aug
1–6 Aug
$1,524 SGD
Show price breakdown
for 5 nights
$1,524 SGD for 5 nights
4.93 out of 5 average rating, 54 reviews
4.93 (54)
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
26–31 Jul
26–31 Jul
$1,610 SGD
Show price breakdown
for 5 nights
$1,610 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom
1 bedroom
,
·
1 bed
1 bed
1–6 Jul
1–6 Jul
$9,143 SGD
Show price breakdown
for 5 nights
$9,143 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Home in Torrington
Beautiful poolside oasis with large cozy home!
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
8–13 Jul
8–13 Jul
$2,126 SGD
Show price breakdown
for 5 nights
$2,126 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms
7 bedrooms
,
·
11 beds
11 beds
8–13 Sept
8–13 Sept
$12,952 SGD
Show price breakdown
for 5 nights
$12,952 SGD for 5 nights
5.0 out of 5 average rating, 33 reviews
5.0 (33)
Top guest favourite
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
21–26 Jul
21–26 Jul
$2,286 SGD
Show price breakdown
for 5 nights
$2,286 SGD for 5 nights
4.99 out of 5 average rating, 244 reviews
4.99 (244)
Guest favourite
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
10–16 Aug
10–16 Aug
$2,393 SGD
Show price breakdown
for 6 nights
$2,393 SGD for 6 nights
4.89 out of 5 average rating, 35 reviews
4.89 (35)
Guest favourite
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
9–14 Aug
9–14 Aug
$3,136 SGD
Show price breakdown
for 5 nights
$3,136 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Home in Litchfield
Charming Victorian | Walk to Litchfield Green
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
5–10 Jul
5–10 Jul
$3,216 SGD
Show price breakdown
for 5 nights
$3,216 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Flat in Torrington
Art House 3 Beds Close to Warner Theater
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
5–10 Jul
5–10 Jul
$1,674 SGD
$1,192 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom
1 bedroom
,
·
1 bed
1 bed
1–6 Aug
1–6 Aug
$886 SGD
Show price breakdown
for 5 nights
$886 SGD for 5 nights
4.91 out of 5 average rating, 140 reviews
4.91 (140)
1
2
3
4
…
15