Over 1,000 places in Winchendon

Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
2 beds
Apr 22 – 27
4.8 out of 5 average rating, 138 reviews
Guest favorite
Home in Winchendon
Copley's Lakefront Cottage and Guest House
7 beds
May 21 – 28
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Winchendon
Amazing Lakefront Home with Pool- Tatum's Place
8 beds
Apr 1 – 6
New place to stay
Superhost
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 beds
Apr 1 – 6
4.87 out of 5 average rating, 38 reviews
Superhost
Home in Winchendon
The Perfect Spot at the Lake @ Tatum's Place
6 beds
Apr 1 – 6
New place to stay
Guest favorite
Guest suite in Ashburnham
The Ginger Bed King Suite
1 king bed
Apr 6 – 11
4.99 out of 5 average rating, 401 reviews
Home in Ashburnham
Tranquil Family Friendly Lakefront Retreat
5 beds
Apr 4 – 9
4.58 out of 5 average rating, 117 reviews
Guest favorite
Guesthouse in Winchendon
Copley’s Guest House on Lake Monomonac
2 beds
Apr 17 – 22
5.0 out of 5 average rating, 22 reviews
Superhost
Home in Winchendon
Lakeview getaway @ Tatum's Place
2 beds
Apr 1 – 6
New place to stay
Guest favorite
Guesthouse in Westminster
Guest House - 4 miles from Wachusett Mt.
1 queen bed
Apr 5 – 10
4.98 out of 5 average rating, 286 reviews
Guest favorite
Home in Rindge
Magic Lakehouse, Waterfront, Private Beach & Dock
7 beds
May 1 – 6
4.9 out of 5 average rating, 21 reviews
Guest favorite
Cottage in Winchendon
Copley's Lakefront Cottage on Lake Monomonac
8 beds
Apr 7 – 12
5.0 out of 5 average rating, 20 reviews
Guest favorite
Cottage in Ashburnham
"Trails End" Lakeside Cottage in Small Town USA
3 beds
Apr 1 – 6
4.92 out of 5 average rating, 98 reviews
Guest favorite
Home in Rindge
Waterfront escape
5 beds
Apr 1 – 6
5.0 out of 5 average rating, 80 reviews
Guest favorite
Guest suite in Fitzwilliam
The Carriage House in Historic Fitzwilliam
1 double bed
Apr 8 – 13
4.96 out of 5 average rating, 283 reviews
Guest favorite
Home in Ashburnham
Escape to the Lake!
5 beds
Apr 29 – May 4
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Rindge
Cottage Cove lakefront home
6 beds
May 12 – 17
5.0 out of 5 average rating, 5 reviews
Farm stay in Gardner
The Hunter Farm
6 beds
Apr 21 – 26
New place to stay