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Our top choices for Winsted holiday homes
1. Peaceful and cozy 1 bed 1 bath in quaint Winchester
Peaceful and cozy 1 bed 1 bath in quaint WinchesterWinchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
Thomas C.
The price is €171
includes taxes & fees
15 Nov - 16 Nov
2. Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville River Escape / Fall Foliage, Deck & YardCollinsville
9.6 out of 10, Exceptional, (4 reviews)
"Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area."
Leah H.
The price is €124
includes taxes & fees
11 Nov - 12 Nov
3. Sun Filled Lake House Living
Sun Filled Lake House LivingAvon
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"
Joseph C.
The price is €227
includes taxes & fees
16 Nov - 17 Nov
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 CollinsvilleCollinsville
10.0 out of 10, Exceptional, (76 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
Mike
The price is €451
includes taxes & fees
8 Nov - 9 Nov
5. The Old Avon 1800 Manor
The Old Avon 1800 ManorAvon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
Anonymous traveller
The price is €372
includes taxes & fees
8 Nov - 9 Nov
6. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
The price is €247
includes taxes & fees
9 Nov - 10 Nov
7. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (155 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."
Dale B.
The price is €313
includes taxes & fees
15 Nov - 16 Nov
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)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
Brian C.
The price is €322
includes taxes & fees
8 Nov - 9 Nov
9. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
Frank M.
The price is €325
includes taxes & fees
8 Nov - 9 Nov
10. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is €368
includes taxes & fees
19 Nov - 20 Nov
11. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
Janet G.
The price is €289
includes taxes & fees
9 Nov - 10 Nov
12. Las Flores Villa
Las Flores VillaNew Preston
10.0 out of 10, Exceptional, (1 review)
The price is €1,273
includes taxes & fees
6 Nov - 7 Nov
13. Maya's Garden House
Maya's Garden HouseGreat Barrington
The price is €1,027
includes taxes & fees
6 Dec - 7 Dec
14. 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!"
Mary R.
The price is €591
includes taxes & fees
16 Nov - 17 Nov
15. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great BarringtonGreat Barrington
The price is €1,128
includes taxes & fees
19 Nov - 20 Nov
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.
Learn more about Winsted
Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes.
