Winsted, CT Vacation Homes from ￥56,253

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

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Our top choices for Winsted vacation homes

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

￥32,823 total

includes taxes & fees

Jul 9 - Jul 10

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

￥74,048 total

includes taxes & fees

Jul 13 - Jul 14

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

Sherwood Forest

Frank M.

￥74,393 total

includes taxes & fees

Jul 7 - Jul 8

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

￥56,253 total

includes taxes & fees

Jul 16 - Jul 17

Big farmhouse in the foothills of the Berkshires

Russell

Will G.

￥57,511 total

includes taxes & fees

Jul 16 - Jul 17

The Old Avon 1800 Manor

Avon

Anonymous traveler

￥77,140 total

includes taxes & fees

Jul 6 - Jul 7

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

￥85,118 total

includes taxes & fees

Jul 7 - Jul 8

Sun Filled Lake House Living

Avon

Joseph C.

￥57,987 total

includes taxes & fees

Jul 18 - Jul 19

Litchfield Retreat, Wineries, Foliage & Skiing

Torrington

￥65,146 total

includes taxes & fees

Jul 5 - Jul 6

Home in Great Barrington

Great Barrington

Julie J.

￥70,179 total

includes taxes & fees

Jul 19 - Jul 20

Stylish Townhome | Perfect for Family Gatherings & Events

Bloomfield

Christina H.

￥120,476 total

includes taxes & fees

Jul 7 - Jul 8

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.

￥110,511 total

includes taxes & fees

Jul 7 - Jul 8

Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

￥81,731 total

includes taxes & fees

Jul 12 - Jul 13

Group-Friendly Townhouse Stay – Sleeps up to 20

Bloomfield

Paul L.

￥220,477 total

includes taxes & fees

Jul 7 - Jul 8

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Top Winsted Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Room was spacious and clean with a comfortable bed. Easy parking, nice quiet location. Easy walk to town."

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent

"First time in Boise for a family wedding and stayed at this surprising hotel. Booked a room with a view. Check in to check out, this place was an easy flow and staff from front desk to dining were especially pleasant and extremely accommodating. Room service did a great job on breakfast, and dinner @ the Riverside Grill was very good. We found the pricing quite reasonable. There were a couple of additional options in food we didn't have time to take advantage of, one outside. The room was sparkly clean, well appointed and well stocked. Beds were firm but comfortable. Nice touch on the robes for use at the hotel as well and the safe for valuables was unexpected. Happy to find the room was a decent size with a sliding glass door to a little patio and small table with two chairs outside that overlooked a nicely groomed grassy lawn with views of the riverwalk in the distance. Hotel is quite large and it can be a walk to get to the front but they even had a shuttle between areas if you need it and happily picked up and dropped off. Traveled with my adult daughter but will say there were lots of families with children enjoying the amenities. I've stayed in many 5 star hotels over the years priced accordingly. For the money, I'd put this property in the highest star category for its class."

Simsbury 1820 House

10/10 Excellent

"Beautiful historic hotel. We had a great comfortable room. The staff we met Sarah and Glen were professional, very helpful and sweet people. The breakfast was very good. No hot eggs, or pancakes etc but it was everything else. Great Great endless coffee. A newspaper to read and it was quiet and very comfortable. I will come back .The restaurant looked fabulous. next time I will try dinner there."

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews	319
Accommodation	297 Vacation Homes
Lowest Price	￥56,253
Highest Price	￥220,477

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winsted vacation homes

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

Real Estate: Therapy - Lake, Laundry, Love it