Winsted Vacation Home Rentals from CA $303: Search Top Private Vacation Homes for Rent

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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

Winchester

Thomas C.

CA $303 total

includes taxes & fees

Nov 1 - Nov 2

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

"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."

Margaret A.

CA $324 total

includes taxes & fees

Nov 2 - Nov 3

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

3. Sun Filled Lake House Living

Avon

Joseph C.

CA $379 total

includes taxes & fees

Oct 26 - Oct 27

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

Collinsville

Mike

CA $751 total

includes taxes & fees

Oct 19 - Oct 20

A patio area with wicker furniture and a brick floor.

5. The Old Avon 1800 Manor

Avon

Anonymous traveller

CA $655 total

includes taxes & fees

Oct 20 - Oct 21

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

Russell

Dale B.

CA $517 total

includes taxes & fees

Oct 22 - Oct 23

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

Sherwood Forest

William C B.

CA $454 total

includes taxes & fees

Nov 3 - Nov 4

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!

Sherwood Forest

Sharon K.

CA $536 total

includes taxes & fees

Oct 14 - Oct 15

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

Sherwood Forest

Frank M.

CA $562 total

includes taxes & fees

Oct 13 - Oct 14

A living room with a sectional sofa, a small side table, and a floor lamp.

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

Plymouth

Iva B.

CA $1,241 total

includes taxes & fees

Oct 13 - Oct 14

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

11. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

CA $607 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Great Barrington

Janet G.

CA $494 total

includes taxes & fees

Oct 13 - Oct 14

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. Treetop Hideaway in Tyringham

Monterey

"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!! "

Samantha G.

CA $808 total

includes taxes & fees

Nov 9 - Nov 10

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.

Great Barrington

Mark M.

CA $1,002 total

includes taxes & fees

Oct 19 - Oct 20

A hot tub in a backyard with a house, trees, and a clear sky.

15. Las Flores Villa

New Preston

CA $4,997 total

includes taxes & fees

Oct 13 - Oct 14

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Top Winsted Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent

"Location, Location, Location... perfect for departing from BDL. Restaurant was very good and bar area was clean and had a wide open area for seating."

Quality Inn Great Barrington

8/10 Good

"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews	347
Accommodation	283 Vacation Homes
Lowest Price	CA $303
Highest Price	CA $4,997

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Our top choices for Winsted vacation homes

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