Photo by Kim Knox Beckius
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Our top choices for Winsted vacation homes
Vacation Home in Goshen
CT Gate House Goshen CT, Gate House Goshen CT9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
Ryan L.
$614 nightly
The price is $629
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
Fred W.
$230 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Sherwood Forest
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Sherwood Forest
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
$351 nightly
The price is $392
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in West Hartford
Charming 1-bedroom in welcoming West Hartford with WiFi, AC$112 nightly
The price is $126
Dec 31 - Jan 1, 2026
Total with taxes and fees
Vacation Home in Avon
Sun Filled Lake House Living6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
Joseph C.
$242 nightly
The price is $256
Jan 7 - Jan 8, 2026
Total with taxes and fees
Vacation Home in Russell
Big farmhouse in the foothills of the Berkshires10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
Kerry P.
$343 nightly
The price is $363
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home in East Granby
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do8.6 out of 10, Excellent, (4)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
Sgt W.
$451 nightly
The price is $511
Jan 2 - Jan 3, 2026
Total with taxes and fees
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
Homewood Suites by Hilton Hartford-Farmington
10/10 Excellent
Find out more about Winsted
Winsted Vacation Homes information
Number of reviews | 332 |
|---|---|
Accommodation | 282 Vacation Homes |
Lowest Price | $256 |
Highest Price | $1,387 |
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