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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winsted holiday homes

A wooden cabin interior with a bench, a rug, and a hanging plant.

1. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is NZ$406
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

2. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, 4, (4 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$513
includes taxes & fees
28 Sept - 29 Sept
Sun Filled Lake House Living
A patio with a table and chairs, a grill, and a view of a lake.

3. 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, 71, (71 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is NZ$835
includes taxes & fees
17 Sept - 18 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A spacious kitchen with a large island, wooden beams, and pendant lighting.

4. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, 43, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is NZ$704
includes taxes & fees
14 Oct - 15 Oct
Linny's - Private Dock - Lake Access - Firepit
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

5. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, 1, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is NZ$474
includes taxes & fees
16 Sept - 17 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A patio area with wicker furniture and a brick floor.

6. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, 2, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is NZ$801
includes taxes & fees
23 Sept - 24 Sept
The Old Avon 1800 Manor
A house with a porch, a garden with pink flowers, and a stone wall along the road.

7. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, 151, (151 reviews)
"Great location"
United States
Will G.
The price is NZ$567
includes taxes & fees
13 Oct - 14 Oct
Big farmhouse in the foothills of the Berkshires
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

8. 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, 9, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$630
includes taxes & fees
15 Sept - 16 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

9. 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, 16, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$680
includes taxes & fees
27 Sept - 28 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, 39, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is NZ$524
includes taxes & fees
15 Sept - 16 Sept
Home in Great Barrington
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

11. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, 44, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$757
includes taxes & fees
27 Sept - 28 Sept
Cheerful 3-bedroom cottage with woodstove
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

12. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, 11, (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 NZ$991
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
A spacious living room with a grey sofa set, a coffee table, and a dining area with a kitchen in the background.

13. Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Bloomfield
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

14. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, 2, (2 reviews)
"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$942
includes taxes & fees
15 Sept - 16 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A bunk bed with a ladder, a bedside table, a lamp, and a window with curtains.

15. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is NZ$1,442
includes taxes & fees
1 Oct - 2 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A hot tub in a backyard with a house, trees, and a clear sky.

16. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, 1, (1 review)
The price is NZ$6,028
includes taxes & fees
1 Oct - 2 Oct
Las Flores Villa
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Amazing new hotel cool airport access great runway views good restaurant access couldn’t be better"
Laura 1-night trip
Posted 6 hours ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
217
Accommodation
277 Holiday Homes
Lowest Price
NZ$406
Highest Price
NZ$6,028