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

Winsted Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winsted vacation 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, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is CA $197
CA $343 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A bedroom with a bed, two bedside tables with lamps, a dresser, and a door.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
The price is CA $180
CA $235 total
includes taxes & fees
Oct 7 - Oct 8
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 CA $106
CA $386 total
includes taxes & fees
Oct 26 - Oct 27
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, (73 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is CA $445
CA $755 total
includes taxes & fees
Oct 21 - Oct 22
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.

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

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were very clean with a warm homey feel. We would definitely stay here again."
United States
Patricia S.
The price is CA $271
CA $544 total
includes taxes & fees
Nov 1 - Nov 2
Linny's - Private Dock - Lake Access - Firepit
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, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is CA $271
CA $667 total
includes taxes & fees
Oct 12 - Oct 13
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, Exceptional, (153 reviews)
"Great location"
United States
Will G.
The price is CA $264
CA $500 total
includes taxes & fees
Oct 12 - Oct 13
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.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 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 CA $127
CA $476 total
includes taxes & fees
Nov 3 - Nov 4
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.

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 CA $208
CA $536 total
includes taxes & fees
Oct 7 - Oct 8
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A living room with a sectional sofa, a small side table, and a floor lamp.

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is CA $494
CA $1,226 total
includes taxes & fees
Oct 7 - Oct 8
Lakehaven • Hot Tub, Decks, Fires & More
A hot tub with a string of lights above it, set against a dark night sky.

11. 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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $228
CA $563 total
includes taxes & fees
Oct 13 - Oct 14
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.

12. 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 CA $266
CA $628 total
includes taxes & fees
Nov 2 - Nov 3
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, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is CA $317
CA $496 total
includes taxes & fees
Oct 13 - Oct 14
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)
"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 CA $391
CA $797 total
includes taxes & fees
Nov 4 - Nov 5
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, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is CA $579
CA $1,011 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $3,848
CA $4,995 total
includes taxes & fees
Oct 8 - Oct 9
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
"The staff was amazing. Super helpful and kind. The room was one of the most beautiful and elegant places we’ve stayed at and the hotel amenities, and restaurant was just something I’ll never forget. Thank you for this experience!"
Andrea 3-night trip
Posted 17 hours ago
Delamar West Hartford

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews
384
Accommodation
283 Vacation Homes
Lowest Price
CA $235
Highest Price
CA $4,995

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