Winchendon Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Winchendon vacation homes

Interior

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 CA $540
CA $715 total
includes taxes & fees
Mar 11 - Mar 12
Enjoy your stay in an antique home in an antique toy museum!
Outdoor spa tub

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is CA $186
CA $399 total
includes taxes & fees
Mar 9 - Mar 10
Modern Downtown 12ppl Hot Tub Fire Pit Games
Fridge, microwave, oven, stovetop

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, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is CA $410
CA $789 total
includes taxes & fees
Mar 5 - Mar 6
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Fridge, microwave, oven, stovetop

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, (2 reviews)
"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.
The price is CA $289
CA $694 total
includes taxes & fees
Mar 23 - Mar 24
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock

3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock
Rindge
The price is CA $922
CA $1,649 total
includes taxes & fees
Mar 5 - Mar 6
3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchendon Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

2/10 Terrible
"No activities for adults. The pool was so packed. I had no head and some of the people I spoke to lied to my face.The only reason I went there was to spend time with my family from VT"
Athena 1-night trip
Posted 20 hours ago
Great Wolf Lodge Boston / Fitchburg, MA

Find out more about Winchendon

Winchendon Vacation Homes information

Number of reviews
58
Accommodation
45 Vacation Homes
Lowest Price
CA $399
Highest Price
CA $1,649

Explore a world of travel with Expedia