Winchendon Vacation Rentals

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Vacation Rentals in Winchendon

Quiet private pond getaway

New Ipswich NH

Located in New Ipswich, this vacation home is in the mountains, within a 15-minute drive of Ashby Wildlife Management Area and Sharon Arts Center.

Modern 6BR Home for Large Groups & Families

Keene NH

Located in Keene, this vacation home is a 4-minute drive from Cheshire Rail Trail and 6 minutes from Historical Society of Cheshire County.

Snow Blanket Barn - Cozy 3BR Family Retreat in Gardner, MA

Gardner MA

With a stay at this vacation home in Gardner, you'll be within a 5-minute drive of Garnder Dog Park and Dunn State Park.

Kitchen

Washer

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

Ashburnham MA

With a stay at this vacation home in Ashburnham, you'll be in the mountains, just steps from Lower Naukeag Lake and a 3-minute drive from Millers River.

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene NH

$332 nightly

$360 total

Sep 22 - Sep 23

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.

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 12!

Orange MA

Located in Orange, this vacation home is on the waterfront, within a 10-minute drive of Royalston Falls and Fish Brook Wildlife Management Area.

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

Westminster MA

Located in Westminster, this vacation home is on a lake, within a 5-minute drive of Wachusett Brewing Company and Wyman Pond.

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Keene NH

$442 nightly

$480 total

Sep 22 - Sep 23

Total with taxes and fees

Free Cancellation

A stay at this vacation home places you in the heart of Keene, within a 10-minute walk of Historic Main Street and CC&H Framing / Pepper Pete's Hot Shop.

Charming 4-bedroom Colonial in lovely Keene with WiFi, AC

Keene NH

With a stay at this vacation home in Keene, you'll be within a 15-minute walk of Historic Main Street and CC&H Framing / Pepper Pete's Hot Shop.

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Westminster MA

With a stay at this vacation home in Westminster, you'll be on the waterfront, just steps from Wyman Pond and a 3-minute drive from Wachusett Lake.

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.

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.

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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.