Photo by Kim Knox Beckius
Search Vacation Homes in Winsted
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 314 Vacation Homes in Winsted with updated reviews, rates, and availability.

Stylish & Luxurious 3 BDR Home with Play Station
Stylish & Luxurious 3 BDR Home with Play Station
9.4 out of 10, Exceptional, (10)

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (150)

Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
10.0 out of 10, Exceptional, (3)

Mountain View Getaway
Mountain View Getaway
10.0 out of 10, Exceptional, (50)

Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (214)

Tranquil Litchfield Connecticut Retreat".
Tranquil Litchfield Connecticut Retreat".
9.2 out of 10, Wonderful, (11)
The price is AED 808
AED 1,152 total
includes taxes & fees
27 Apr - 28 Apr

The Race Mountain House
The Race Mountain House
10.0 out of 10, Exceptional, (1)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Winsted

The Cottage at Highland Lake, year-round, waterfront with a boat dock
The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (4)

Family House On Highland Lake with Dock
Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (24)

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
9.0 out of 10, Wonderful, (12)
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.
Recent reviews of Winsted hotels
Recent reviews of Winsted hotels

DoubleTree by Hilton Hartford - Bradley Airport
5/5 Excellent
"It was wonderful "
A verified traveler stayed at DoubleTree by Hilton Hartford - Bradley Airport
Posted 5 hours ago