Search Vacation Homes in Winchendon

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Dec 12 - Dec 14
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Dec 19 - Dec 21
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Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Vacation Homes in Winchendon

Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Keene
9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
$256 nightly
The price is $277
Dec 7 - Dec 8
Total with taxes and fees
Downtown Hot Tub Escape
Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

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

Westminster
10.0 out of 10, Exceptional, (25)
"The house had everything our family needed for a fun and relaxing stay. Great house and yard on a beautiful spot on the lake! Highly recommend!!"
United States
Carol W.
$451 nightly
The price is $495
Dec 14 - Dec 15
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Interior
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Dublin
10.0 out of 10, Exceptional, (25)
"Good place to stay during a wedding week"
United States
Veronique S.
$541 nightly
The price is $572
Dec 7 - Dec 8
Total with taxes and fees
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Outdoor dining
Charming Home Walk to Downtown!

Charming Home Walk to Downtown!

Keene
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
$571 nightly
The price is $620
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming Home Walk to Downtown!
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.
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Top Winchendon Hotel Reviews

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

10/10 Excellent
"Very clean. Staff was friendly. "
Bryan 1-night trip
Posted 3 days ago
Doubletree by Hilton Hotel Leominster

Find out more about Winchendon

Winchendon Vacation Homes information

Number of reviews
72
Accommodation
49 Vacation Homes
Lowest Price
$277
Highest Price
$620

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