Winchester Vacation Rentals

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Vacation Rentals in Winchester

Lovely 2nd Floor Apartment

Greenfield MA

$181 nightly

$202 total

May 11 - May 12

Total with taxes and fees

Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.

Kitchen

Air conditioning

Lakefront 3BR Log Cabin w/ Dock and Fire Pit

Rindge NH

When you stay at this vacation home in Rindge, you'll be on the waterfront, just steps from Contoocook Lake and Jowder's Cove Beach.

Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking

Leyden MA

Located in Greenfield, this vacation home is in the mountains, a 4-minute drive from Leyden Town Hall and 6 minutes from Robertson Memorial Library.

Willow Falls Home ~ Hot Tub & Waterfront

Jaffrey NH

With a stay at this vacation home in Jaffrey, you'll be within a 5-minute drive of Cathedral of the Pines and Contoocook Lake.

Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Shelburne Falls MA

With a stay at this vacation home in Shelburne Falls, you'll be a 1-minute walk from Deerfield River and 7 minutes by foot from Arms Cemetery.

River House

Brookline VT

With a stay at this vacation home in Newfane, you'll be on the waterfront, just steps from West River and a 3-minute drive from Newfane Town Hall.

Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access

Westminster VT

Located in Westminster, this vacation home is within a 5-minute drive of Connecticut River and Pete's Stand Vegetables.

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT

Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Peterborough NH

When you stay at this vacation home in Peterborough, you'll be in the mountains, within a 5-minute drive of Ava Marie Handmade Chocolates and The Monadnock Center for History and Culture.

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene NH

$276 nightly

$299 total

May 6 - May 7

Total with taxes and fees

With a stay at this vacation home in Keene, you'll be within a 10-minute walk of Cheshire Rail Trail and Historic Main Street.

Cozy Lakefront Cottage

Winchendon MA

Located in Winchendon, this vacation home is on the waterfront, a 2-minute drive from Blueberry Island and 6 minutes from Winchendon Community Park.

Kitchen

Washer

The Jelly Mill-A Peaceful River Retreat

Guilford VT

When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.

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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.