Holiday Homes in Winsted

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Winsted holiday homes

Smart TV, books

Holiday Home in Sherwood Forest

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is NZ$654
includes taxes & fees
15 Mar - 16 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Private kitchen

Holiday Home in Torrington

Litchfield Retreat, Wineries, Foliage & Skiing
The price is NZ$667
includes taxes & fees
14 Mar - 15 Mar
Litchfield Retreat, Wineries, Foliage & Skiing
Exterior detail

Holiday Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is NZ$1,077
includes taxes & fees
18 Mar - 19 Mar
CT Gate House Goshen CT, Gate House Goshen CT
Property grounds

Holiday Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is NZ$611
includes taxes & fees
14 Mar - 15 Mar
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is NZ$459
includes taxes & fees
15 Mar - 16 Mar
Home in Great Barrington
Interior

Holiday Home in Bloomfield

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
7.6 out of 10, Good, (4 reviews)
"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.
The price is NZ$1,452
includes taxes & fees
14 Mar - 15 Mar
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Property grounds

Holiday Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$845
includes taxes & fees
23 Mar - 24 Mar
Cheerful 3-bedroom cottage with woodstove
TV

Holiday Home in Monterey

Treetop Hideaway in Tyringham
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is NZ$928
includes taxes & fees
16 Mar - 17 Mar
Treetop Hideaway in Tyringham
Exterior

Holiday Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is NZ$998
includes taxes & fees
14 Mar - 15 Mar
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Dining

Holiday Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is NZ$1,459
includes taxes & fees
14 Mar - 15 Mar
Whispering Estate Guest House - A Romantic Countryside Getaway
Property grounds

Holiday Home in Avon

Sun Filled Lake House Living
6.0 out of 10, (3 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is NZ$446
includes taxes & fees
7 Apr - 8 Apr
Sun Filled Lake House Living
3 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is NZ$1,109
includes taxes & fees
6 Apr - 7 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop

Holiday Home in Bloomfield

Premium 3-Story Townhome | Perfect for Large Groups
9.4 out of 10, Exceptional, (6 reviews)
"Great stay. "
United States
Le Dung H.
The price is NZ$1,109
includes taxes & fees
18 Mar - 19 Mar
Premium 3-Story Townhome | Perfect for Large Groups
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

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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

Springhill Suites Marriott Airport

Springhill Suites Marriott Airport

8/10 Good
"Room set up was odd, and walls were thin could hear lots of noise. Staff great and bed super comfy!"
Candie 1-night trip
Posted 8 hours ago
Springhill Suites Marriott Airport

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
260
Accommodation
272 Holiday Homes
Lowest Price
NZ$446
Highest Price
NZ$1,459