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Vacation rentals in Winchendon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchendon

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest suite in Ashburnham
The Ginger Bed King Suite
Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!
$95 per night
Guesthouse in New Ipswich
"The Porch" Your cozy home away from home!
Welcome to The Porch! Ready for a mini vacation, or just a place to hang out at, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person rentals. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome!
$82 per night
Guesthouse in Westminster
Guest House - 4 miles from Wachusett Mt.
Enjoy your stay in this cozy, newly renovated semi-attached in-law unit. It is located close to Route 2, walking distance to the town center, only 4 miles from Mt. Wachusett in a quiet neighborhood. It has 2 parking spaces and a private entrance. This unique space has everything to make you feel at home – including WiFi and Netflix. The kitchen is equipped with a Keurig Coffee Maker, Mini Fridge, and a Microwave. Queen-size bed, fresh towels, body wash are also provided.
$97 per night

Other great vacation rentals in Winchendon

Cottage in Orange
The Lake Cottage: A Sweetwater Stay
$91 per night
Apartment in Dublin
Private Dublin apartment nestled in the woods
$110 per night
Guest suite in Milford
Spacious Souhegan Getaway
$98 per night
Guesthouse in Wilton
Cottage beside a waterfall
$149 per night
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
$150 per night
Cabin in Harrisville
Trailside Cottage in charming Harrisville, NH
$147 per night
Guest suite in Amherst
Bright, peaceful suite in great location!
$79 per night
Guesthouse in Winchendon
Copley’s Guest House on Lake Monomonac
$135 per night
Apartment in Westminster
Modern Farmhouse Apartment
$150 per night
Home in Ashburnham
Lake House with Island and boats!
$199 per night
Home in Rindge
The Crowcroft House
$246 per night
Cabin in Fitzwilliam
Cozy Log Cabin Mountain Views
$135 per night

Destinations to explore