A hilly landscape with a tower on top, dense forest, and a cloudy sky.

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Our top choices for Winchendon vacation homes

Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (8 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is AED 1,194
AED 1,440 total
includes taxes & fees
21 Jun - 22 Jun
Enjoy your stay in an antique home in an antique toy museum!

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (26 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is AED 812
AED 1,443 total
includes taxes & fees
21 Jun - 22 Jun
Modern Downtown Escape HotTub Fire Pit Games 12ppl

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AED 705
AED 1,761 total
includes taxes & fees
22 Jun - 23 Jun
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
10.0 out of 10, Exceptional, (1 review)
"Everything we needed"
United States
Lori S.
The price is AED 1,087
AED 2,005 total
includes taxes & fees
8 Jul - 9 Jul
John's Mountain Hideaway

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, (37 reviews)
"We had a wonderful stay at this lake-front cottage looking up at the nearby ski resort. The cottage was cozy and quiet in a great location. The check-in process was easy, and the owner was very accessible. Terrific rental!"
United States
Lane D.
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
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

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