Holiday Homes in Winchendon

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Winchendon and around

Our top choices for Winchendon holiday homes

Cottage beside a waterfall
Property grounds

Cottage beside a waterfall

9.4 out of 10, Exceptional, (3)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
The price is €228
includes taxes & fees
1 Sept - 2 Sept
Cottage beside a waterfall
River Room overlooking the waterfall
Outdoor dining

River Room overlooking the waterfall

10.0 out of 10, Exceptional, (1)
"Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too."
The price is €228
includes taxes & fees
1 Sept - 2 Sept
River Room overlooking the waterfall
earthship forest exile
Fridge, microwave, oven, stovetop

earthship forest exile

10.0 out of 10, Exceptional, (5)
"Great house for myself and my staff who run the NEW HAMPSHIRE OUTDOOR EXPO to stay and chill. House is clean, nice layout and the woodstove is awesome. We will be coming back to this property as our event is ANNUAL."
earthship forest exile
Cozy 2-bedroom RV with WiFi, AC in welcoming Orange
Private kitchen

Cozy 2-bedroom RV with WiFi, AC in welcoming Orange

The price is €274
includes taxes & fees
4 Sept - 5 Sept
Cozy 2-bedroom RV with WiFi, AC in welcoming Orange
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (7)
"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "
The price is €484
includes taxes & fees
25 Aug - 26 Aug
Cozy Home Near Downtown, Shops, and Restaurants.
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is €370
includes taxes & fees
24 Aug - 25 Aug
Downtown Hot Tub Escape
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Interior

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

10.0 out of 10, Exceptional, (23)
"Good place to stay during a wedding week"
The price is €636
includes taxes & fees
26 Aug - 27 Aug
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
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.
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

10/10 Excellent
"I like the bed comfort and the tv!!"
ERIC 1-night trip
Posted 4 days ago
Great Wolf Lodge Boston / Fitchburg, MA