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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is AU$305
includes taxes & fees
15 Nov - 16 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

2. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.0 out of 10, Wonderful, (2 reviews)
"Lots of care provided for guests. We unfortunately did not have opportunity to take advantage of many of the amenities but enjoyed our stay."
United States
Judy L.
The price is AU$322
includes taxes & fees
2 Nov - 3 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

3. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (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 AU$377
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A patio with a table and chairs, a grill, and a view of a lake.

4. 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, (74 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$703
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A patio area with wicker furniture and a brick floor.

5. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is AU$635
includes taxes & fees
20 Oct - 21 Oct
The Old Avon 1800 Manor
A house with a porch, a garden with pink flowers, and a stone wall along the road.

6. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AU$506
includes taxes & fees
22 Oct - 23 Oct
Big farmhouse in the foothills of the Berkshires
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"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 AU$442
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A living room with a sectional sofa, a small side table, and a floor lamp.

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Great find!! Amazing views, house was superb!"
United States
Iva B.
The price is AU$1,089
includes taxes & fees
26 Oct - 27 Oct
Lakehaven • Hot Tub, Decks, Fires & More
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.

9. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$525
includes taxes & fees
27 Oct - 28 Oct
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.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$551
includes taxes & fees
29 Oct - 30 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$605
includes taxes & fees
11 Nov - 12 Nov
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$503
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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$787
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
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, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is AU$1,021
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A hot tub in a backyard with a house, trees, and a clear sky.

15. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AU$5,046
includes taxes & fees
18 Oct - 19 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

Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"All good"
Robert 1-night trip
Posted 1 hour ago
Delamar West Hartford

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
349
Accommodation
295 Holiday Homes
Lowest Price
AU$305
Highest Price
AU$5,046