A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

Holiday Homes in Winsted

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winsted holiday homes

2 bedrooms, free WiFi, bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AU$295
includes taxes & fees
20 July - 21 July
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$494
includes taxes & fees
16 July - 17 July
Real Estate: Therapy - Lake, Laundry, Love it
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, (148 reviews)
"Great location"
United States
Will G.
The price is AU$508
includes taxes & fees
15 July - 16 July
Big farmhouse in the foothills of the Berkshires
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$680
includes taxes & fees
27 July - 28 July
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (40 reviews)
"Everything was spectacular from the check in process to the personal experiences."
United States
leigh
The price is AU$546
includes taxes & fees
5 Aug - 6 Aug
Linny's - Lakefront Retreat Private Dock & Firepit
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 AU$433
includes taxes & fees
30 July - 31 July
Sun Filled Lake House Living
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is AU$558
includes taxes & fees
19 July - 20 July
Home in Great Barrington
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 AU$645
includes taxes & fees
27 July - 28 July
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AU$985
includes taxes & fees
15 July - 16 July
Treetop Hideaway in Tyringham
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Bloomfield
8.0 out of 10, Very good, (5 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 AU$1,042
includes taxes & fees
21 July - 22 July
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$751
includes taxes & fees
30 July - 31 July
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (49 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is AU$3,436
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
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.
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Top Winsted Hotel Reviews

Springhill Suites Marriott Airport

Springhill Suites Marriott Airport

10/10 Excellent
"Room was spacious, clean, staff were extremely helpful and friendly. They have tea and coffee and a great breakfast!!"
Kara 1-night trip
Posted 2 hours ago
Springhill Suites Marriott Airport

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
10,331
Accommodation
297 Holiday Homes
Lowest Price
AU$135
Highest Price
AU$414