Photo by Kim Knox Beckius

Search Vacation Homes in Winsted

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Homes in Winsted

Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$641 nightly
The price is $659
Nov 25 - Nov 26
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Private kitchen
Home in the Woods

Vacation Home in Russell

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
$303 nightly
The price is $320
Nov 30 - Dec 1
Total with taxes and fees
Home in the Woods
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Dec 1 - Dec 2
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Property grounds
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Vacation Home in East Granby

8.6 out of 10, Excellent, (4)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
$387 nightly
The price is $439
Nov 25 - Nov 26
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Dec 1 - Dec 2
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Vacation Home in Bloomfield

2.0 star property
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
$530 nightly
The price is $601
Nov 25 - Nov 26
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
$244 nightly
The price is $272
Dec 1 - Dec 2
Total with taxes and fees
Home in Great Barrington
Property grounds
Big farmhouse in the foothills of the Berkshires

Vacation Home in Russell

10.0 out of 10, Exceptional, (143)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
United States
Jon O.
$344 nightly
The price is $364
Nov 25 - Nov 26
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Smart TV, fireplace
Sun Filled Lake House Living

Vacation Home in Avon

2.0 star property
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
$265 nightly
The price is $283
Dec 11 - Dec 12
Total with taxes and fees
Sun Filled Lake House Living
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$450 nightly
The price is $503
Nov 25 - Nov 26
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (25)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
$464 nightly
The price is $518
Nov 25 - Nov 26
Total with taxes and fees
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Vacation Home in Collinsville

10.0 out of 10, Exceptional, (61)
"A very nice period home in a beautiful setting. The home is immaculate with all of the necessary essentials for an extended stay. The host is very responsive and keeps in touch to ensure that your stay is as enjoyable and comfortable as possible. "
United States
Virginia M.
$433 nightly
The price is $491
Nov 30 - Dec 1
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
2 bedrooms, iron/ironing board, WiFi, bed sheets
Litchfield Retreat, Wineries, Foliage & Skiing

Vacation Home in Torrington

2.0 star property
$318 nightly
The price is $360
Nov 30 - Dec 1
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
Property grounds
Charming 3-bedroom Modern cottage with lakeside views

Vacation Home in Hartland

2.0 star property
$1,314 nightly
The price is $1,487
Nov 27 - Nov 28
Total with taxes and fees
Charming 3-bedroom Modern cottage with lakeside views
Property grounds
Stylish Townhome | Perfect for Family Gatherings & Events

Vacation Home in Bloomfield

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
$530 nightly
The price is $601
Nov 25 - Nov 26
Total with taxes and fees
Stylish Townhome | Perfect for Family Gatherings & Events
Interior
Group-Friendly Townhouse Stay – Sleeps up to 20

Vacation Home in Bloomfield

$939 nightly
The price is $1,064
Dec 7 - Dec 8
Total with taxes and fees
Group-Friendly Townhouse Stay – Sleeps up to 20
Fridge, microwave, oven, stovetop
Premium 3-Story Townhome | Perfect for Large Groups

Vacation Home in Bloomfield

2.0 star property
9.2 out of 10, Wonderful, (5)
"Great stay. "
United States
Le Dung H.
$610 nightly
The price is $691
Dec 3 - Dec 4
Total with taxes and fees
Premium 3-Story Townhome | Perfect for Large Groups
Fridge, microwave, oven, stovetop
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Vacation Home in Bloomfield

$915 nightly
The price is $1,040
Dec 7 - Dec 8
Total with taxes and fees
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winsted Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent
"All good "
Walter 1-night trip
Posted 18 hours ago
DoubleTree by Hilton Hotel Bristol, Connecticut

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews
333
Accommodation
282 Vacation Homes
Lowest Price
$272
Highest Price
$1,487

Explore a world of travel with Expedia