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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 NZ$335
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.4 out of 10, Exceptional, (3 reviews)
"This was a great weekend away in CT! The house was comfortable and clean. Very cozy setup and good communication with the host. The weather wasn’t amazing but we still enjoyed our stay for the weekend."
United States
Brandon R.
The price is NZ$354
includes taxes & fees
4 Nov - 5 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 NZ$438
includes taxes & fees
17 Nov - 18 Nov
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, (76 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is NZ$815
includes taxes & fees
2 Nov - 3 Nov
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 NZ$757
includes taxes & fees
4 Nov - 5 Nov
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, (154 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 NZ$606
includes taxes & fees
2 Nov - 3 Nov
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 NZ$488
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
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, Exceptional, (10 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
2 Nov - 3 Nov
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
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$651
includes taxes & fees
2 Nov - 3 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A hot tub in a covered outdoor area with a view of trees and a fence.

10. 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.
Lakehaven • Hot Tub, Decks, Fires & More
A modern living room with a sofa, coffee table, and a dining area with chairs.

11. #11 | Beds for 8, up to 14 with approval

#11 | Beds for 8, up to 14 with approval
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
#11 | Beds for 8, up to 14 with approval
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

12. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$709
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

13. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is NZ$561
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

14. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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$944
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.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 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$1,164
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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, Exceptional, (1 review)
The price is NZ$2,539
includes taxes & fees
2 Nov - 3 Nov
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Quaint hotel in an ideal location."
Kimberley 5-night trip
Posted 18 hours ago
Avon Old Farms Hotel

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
330
Accommodation
277 Holiday Homes
Lowest Price
NZ$335
Highest Price
NZ$2,539