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
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Winsted holiday homes

Fridge, microwave, oven, stovetop

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Relaxing stay"
United States
Kim M.
The price is NZ$715
includes taxes & fees
30 Apr - 1 May
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is NZ$660
includes taxes & fees
6 May - 7 May
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (145 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is NZ$581
includes taxes & fees
6 May - 7 May
Big farmhouse in the foothills of the Berkshires
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$627
includes taxes & fees
6 May - 7 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
10.0 out of 10, Exceptional, (5 reviews)
"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.
The price is NZ$1,108
includes taxes & fees
30 Apr - 1 May
Stylish Townhome | Perfect for Family Gatherings & Events
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is NZ$671
includes taxes & fees
5 May - 6 May
Litchfield Retreat, Wineries, Foliage & Skiing
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (29 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$536
includes taxes & fees
6 May - 7 May
Home in Great Barrington
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (64 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is NZ$873
includes taxes & fees
14 May - 15 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
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$843
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is NZ$549
includes taxes & fees
19 May - 20 May
Real Estate: Therapy - Lake, Laundry, Love it
Interior

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (26 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is NZ$1,264
includes taxes & fees
11 May - 12 May
Modern Victorian Walk to Main Street
Smart TV

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Bloomfield
9.0 out of 10, Wonderful, (6 reviews)
"I had a great time and I felt very welcome"
United States
Avis b.
The price is NZ$1,157
includes taxes & fees
30 Apr - 1 May
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
TV, fireplace

73R Brand new log home on quiet side street in Bethlehem, close to Main Street, AC, Dog Friendly!

73R Brand new log home on quiet side street in Bethlehem, close to Main Street, AC, Dog Friendly!
Bethlehem
8.8 out of 10, Excellent, (14 reviews)
"Property was great spacious enough for family and close to shops "
United States
robert h.
The price is NZ$1,660
includes taxes & fees
30 Apr - 1 May
73R Brand new log home on quiet side street in Bethlehem, close to Main Street, AC, Dog Friendly!
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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$938
includes taxes & fees
4 May - 5 May
Treetop Hideaway in Tyringham
Terrace/patio

The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
The price is NZ$820
includes taxes & fees
4 May - 5 May
The Old Avon 1800 Manor
Property grounds

Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
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$468
includes taxes & fees
20 May - 21 May
Sun Filled Lake House Living
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
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$860
includes taxes & fees
30 Apr - 1 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Bloomfield
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$1,060
includes taxes & fees
3 May - 4 May
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is NZ$1,474
includes taxes & fees
30 Apr - 1 May
Whispering Estate Guest House - A Romantic Countryside Getaway
Interior

Group-Friendly Townhouse Stay – Sleeps up to 20

Group-Friendly Townhouse Stay – Sleeps up to 20
Bloomfield
8.0 out of 10, Very good, (3 reviews)
"This was a terrific spot for our weekend plans to fly in and see a UCONN Husky basketball game in Hartford! Hope was comfortable and clean. Will definitely plan to stay here again. "
United States
Paul L.
Group-Friendly Townhouse Stay – Sleeps up to 20
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
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Breakfast was great. Lovely hotel "
claire 1-night trip
Posted 6 hours ago
Avon Old Farms Hotel

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
375
Accommodation
293 Holiday Homes
Lowest Price
NZ$468
Highest Price
NZ$1,660