Search Vacation Homes in Winchendon
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Winchendon vacation homes
1. 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, (9 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!!!"
Katja Z.
The price is AED 1,194
AED 1,425 total
includes taxes & fees
27 Sep - 28 Sep
2. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.Fitzwilliam
The price is AED 876
AED 1,086 total
includes taxes & fees
14 Sep - 15 Sep
3. Modern Downtown Escape HotTub Fire Pit Games 12ppl
Modern Downtown Escape HotTub Fire Pit Games 12pplKeene
9.4 out of 10, Exceptional, (26 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
cody s.
The price is AED 658
AED 1,256 total
includes taxes & fees
14 Sep - 15 Sep
4. 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, (4 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."
Jeremy S.
The price is AED 705
AED 1,761 total
includes taxes & fees
14 Sep - 15 Sep
5. 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 RegionDublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
Veronique S.
The price is AED 1,543
AED 2,642 total
includes taxes & fees
14 Sep - 15 Sep
6. Serene & Sleek Family Retreat w/ Office in Shirley
Serene & Sleek Family Retreat w/ Office in ShirleyShirley
The price is AED 907
AED 2,337 total
includes taxes & fees
24 Sep - 25 Sep
The price is AED 1,041
AED 2,351 total
includes taxes & fees
23 Sep - 24 Sep
8. Entire home in Sterling, Massachusetts, United States
Entire home in Sterling, Massachusetts, United StatesSterling
The price is AED 1,041
AED 2,714 total
includes taxes & fees
12 Oct - 13 Oct
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.
Find vacation rentals that suit your style
Cabins
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Winchendon Hotel Reviews
Centennial House
10/10 Excellent
