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Vacation rentals in Winchendon

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Top-rated vacation rentals in Winchendon

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

The Ginger Bed King Suite
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath
The Ginger Bed King SuiteCome 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!
The Carriage House in Historic Fitzwilliam
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath
The Carriage House in Historic FitzwilliamWelcome to the Carriage House! Former site of the popular Hannah Davis House Bed and Breakfast, this gorgeous space is ready for your visit! Beautiful wood beams throughout, a cozy loft bedroom, and a completely separate entrance for privacy. Short rides to Rhododendron State Park, Mount Monadnock, Gap Mountain, the Cheshire Rail Trail, Laurel Lake, and many more outdoor activities year round. Walking distance to the town common in a town where little has changed and history is preserved.
The Old Red Mill COTTAGE (beside a waterfall)
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath
The Old Red Mill COTTAGE (beside a waterfall)Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, chickens and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

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Other great vacation rentals in Winchendon

SUPERHOST
  1. Entire cottage
  2. Orange
The Fishing Cottage: A Sweetwater Stay
$119 per night
SUPERHOST
  1. Entire guesthouse
  2. New Ipswich
"The Porch" Your cozy home away from home!
$74 per night
  1. Entire residential home
  2. Orange
4-season Lake House with Fireplace & Private Dock
$120 per night
SUPERHOST
  1. Yurt
  2. Rindge
Enchanting solar powered yurt in small community
$85 per night
SUPERHOST
  1. Entire cottage
  2. Petersham
Cider House Cottage
$150 per night
SUPERHOST
  1. Entire cottage
  2. Orange
The Film Shack: A Sweetwater Stay
$86 per night
SUPERHOST
  1. Entire cabin
  2. Rindge
Beautiful Lakefront Log Cabin
$230 per night
SUPERHOST
  1. Entire guest suite
  2. Peterborough
Meadow View
$95 per night
SUPERHOST
  1. Entire cabin
  2. Rindge
Waterfront Log Home on Lake Contoocook
$262 per night
  1. Private room
  2. Athol
Cheerful Room in Large Cape
$65 per night
SUPERHOST
  1. Entire cottage
  2. Ashburnham
"Trails End" Lakeside Cottage in Small Town USA
$195 per night
SUPERHOST
  1. Entire cottage
  2. Temple
Cottage Country Get Away
$122 per night