Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Winchester
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Skiing
Countryside
Cabins
Amazing pools
Rooms
Amazing views
Farms
Vineyards
Lakefront
Play
Chef's kitchens
Bed & breakfasts
Ski-in/out
Tiny homes
Design
Barns
Grand pianos
New
Trending
Off-the-grid
Camping
Mansions
Golfing
A-frames
Creative spaces
OMG!
Yurts
Domes
Treehouses
Lake
Filters
, 1 filter applied
1
Display total before taxes
Show map
Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Home in Winsted
Newly renovated lakefront home!
7 beds
7 beds
Apr 1 – 6
Apr 1 – 6
G$62,992 GYD
night
G$62,992 GYD per night
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Guest favorite
Guest favorite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4 beds
4 beds
Apr 17 – 22
Apr 17 – 22
G$32,620 GYD
night
G$32,620 GYD per night
5.0 out of 5 average rating, 79 reviews
5.0 (79)
Guest favorite
Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
1 bed
Apr 1 – 6
Apr 1 – 6
G$22,105 GYD
night
G$22,105 GYD per night
4.94 out of 5 average rating, 34 reviews
4.94 (34)
Superhost
Superhost
Apartment in Winsted
Haven at Highland lake
2 beds
2 beds
Apr 8 – 13
Apr 8 – 13
G$19,030 GYD
night
G$19,030 GYD per night
4.85 out of 5 average rating, 60 reviews
4.85 (60)
Guest favorite
Guest favorite
Home in Winsted
Lake House- Great for Families
7 beds
7 beds
Apr 11 – 16
Apr 11 – 16
G$83,791 GYD
G$72,983 GYD
night
G$72,983 GYD per night, originally G$83,791 GYD
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Guest favorite
Guest favorite
Apartment in Winchester
Gateway to the Berkshires
2 beds
2 beds
Apr 12 – 17
Apr 12 – 17
G$23,902 GYD
night
G$23,902 GYD per night
4.91 out of 5 average rating, 338 reviews
4.91 (338)
Superhost
Superhost
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
G$32,082 GYD
night
G$32,082 GYD per night
4.87 out of 5 average rating, 30 reviews
4.87 (30)
Guest favorite
Guest favorite
Guesthouse in New Hartford
Litchfields West Hill New Hartford Four Season BNB
3 beds
3 beds
Apr 14 – 19
Apr 14 – 19
G$21,571 GYD
night
G$21,571 GYD per night
4.86 out of 5 average rating, 79 reviews
4.86 (79)
Guest favorite
Guest favorite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
G$50,467 GYD
G$27,009 GYD
night
G$27,009 GYD per night, originally G$50,467 GYD
4.94 out of 5 average rating, 51 reviews
4.94 (51)
Apartment in Winsted
Peaceful country getaway from the hectic city life
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
G$29,510 GYD
night
G$29,510 GYD per night
4.89 out of 5 average rating, 36 reviews
4.89 (36)
Guest favorite
Guest favorite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a lake beach!
3 queen beds
3 queen beds
Apr 7 – 12
Apr 7 – 12
G$48,099 GYD
night
G$48,099 GYD per night
4.96 out of 5 average rating, 27 reviews
4.96 (27)
Superhost
Superhost
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
3 beds
3 beds
Apr 7 – 12
Apr 7 – 12
G$48,513 GYD
night
G$48,513 GYD per night
Guest favorite
Guest favorite
Cabin in Colebrook
Adorable, storybook log cabin
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
G$62,913 GYD
night
G$62,913 GYD per night
4.94 out of 5 average rating, 196 reviews
4.94 (196)
Guest favorite
Guest favorite
Home in Winchester
Winchester House with wifi/high speed internet.
6 beds
6 beds
Apr 1 – 7
Apr 1 – 7
G$63,927 GYD
night
G$63,927 GYD per night
4.87 out of 5 average rating, 23 reviews
4.87 (23)
Guesthouse in Winchester
Year-round Lakefront Highland Lake - Immaculate
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
G$54,370 GYD
night
G$54,370 GYD per night
4.97 out of 5 average rating, 59 reviews
4.97 (59)
Guest favorite
Guest favorite
123
Reviews
4.89
Rating
8
Years hosting
Room in Barkhamsted
Stay with Judith
Stay with Judith
Hosting for 8 years
,
·
Hosting for 8 years
Sweet Suite in Lakefront Chalet-pvt bath
Apr 1 – 6
Apr 1 – 6
G$31,789 GYD
night
G$31,789 GYD per night
4.89 out of 5 average rating, 123 reviews
4.89 (123)
Home in Winsted
Beecher Pond Idyll
5 beds
5 beds
Jul 14 – 19
Jul 14 – 19
G$72,296 GYD
night
G$72,296 GYD per night
Guest favorite
Guest favorite
Cabin in New Hartford
West Hill Cabin
4 beds
4 beds
Apr 10 – 15
Apr 10 – 15
G$52,439 GYD
G$44,836 GYD
night
G$44,836 GYD per night, originally G$52,439 GYD
5.0 out of 5 average rating, 33 reviews
5.0 (33)
1
2
3
4
…
15