Winsted Vacation Rentals

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Vacation Rentals in Winsted

Litchfield County Getaway

Warren CT

Located in Cornwall Bridge, this vacation home is in a rural location, within a 15-minute drive of Above All State Park and Hopkins Vineyard.

Kitchen

Washer

The Meadows House @ Otis Ridge w/ 7-person hot tub

Otis MA

When you stay at this vacation home in Otis, you'll be in the mountains, within a 10-minute walk of Lift Line and Slalom.

Hot Tub

Kitchen

Private Annex/Former Artist Studio

Washington CT

When you stay at this vacation home in New Preston, you'll be on a lake, within a 5-minute walk of Mount Bushnell State Park and Lake Waramaug.

Kitchen

Pet friendly

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington MA

A stay at this vacation home places you in the heart of Great Barrington, within a 10-minute walk of Housatonic River Walk and Housatonic River.

Kitchen

Washer

The Goshen Glass Chalet

Goshen CT

Located in Goshen, this vacation home is a 2-minute drive from Woodridge Lake and 6 minutes from Goshen Historic District.

Hot Tub

Kitchen

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis MA

With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 5-minute drive from County Beach.

Kitchen

Washer

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

Goshen CT

Located in Goshen, this vacation home is within a 5-minute drive of Woodridge Lake and Miranda Vineyard.

Hot Tub

Kitchen

Beautiful retreat in a lake community to the enjoy the summer season.

Tolland MA

With a stay at this vacation home in Granville, you'll be on a lake, and 5.5 mi (8.9 km) from Phelon Memorial Forest and 6.1 mi (9.8 km) from Otis Reservoir.

Kitchen

Dryer

Peace and quiet on the lake

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

Lakefront Fall Foliage in New England Just 2 Hours From NYC

Sharon CT

Located in Sharon, this vacation home is on the waterfront, a 1-minute drive from Indian Lake and 6 minutes from North East Town Hall.

Kitchen

Pet friendly

Hilltop Escape with Views & Hot Tub

New Marlborough MA

Located in Great Barrington, this vacation home is a 4-minute drive from Dry Hill and 5 minutes from New Marlborough Town Hall.

Hot Tub

Kitchen

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT

With a stay at this vacation home in Winsted, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

Kitchen

Washer

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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.