Winchester Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Winchester hotels

Vacation Rentals in Winchester

Antique Farmhouse Totally Restored

Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Mount Riga State Park and Mount Everett State Reservation.

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Located in Bantam, this vacation home is on the waterfront, a 4-minute drive from Mount Tom State Park and 6 minutes from Bantam Lake.

Charming 1870 cape cottage in Litchfield

With a stay at this vacation home in Litchfield, you'll be within a 5-minute drive of White Memorial Conservation Center and Bantam Lake.

Majestic Mountain Side Sheffield/Great Barrington/SKI

With a stay at this vacation home in Sheffield, you'll be in the mountains, just a 1-minute walk from Housatonic River and 14 minutes by foot from Lime Kiln Farm Wildlife Sanctuary.

Relax or be active! The choice is yours in this pet-friendly family home.

With a stay at this vacation home in Norfolk, you'll be within a 10-minute walk of Norfolk Historical Museum and Infinity Music Hall and Bistro.

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

With a stay at this vacation home in Kent, you'll be a 4-minute walk from Eric Sloane Museum and Kent Iron Furnace and 12 minutes by foot from Seven Hearths Museum.

Washer

Dryer

Big farmhouse in the foothills of the Berkshires

$382

includes taxes & fees

$361 per night

Jan 5 - Jan 6

Located in Russell, this vacation home is within a 10-minute drive of Westfield River and Strathmore Park.

Kitchen

Washer

Peaceful, Post and Beam Loft, Sleeps 9

Located in Great Barrington, this vacation home is within a 5-minute drive of Lake Buel and Dry Hill.

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

With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.

Kitchen

Washer

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

Located in Bristol, this vacation home is within a 5-minute drive of Casey Field and Wilson Playground.

The Goshen Glass Chalet

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

Charming 3BR Hilltop House, Newly Remodeled with Arcade

Located in Terryville, this vacation home is a 5-minute drive from Witch's Dungeon Classic Movie Museum and 5 minutes from B.A.R.K Dog Park.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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.