Search Chalets in Winchendon

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Compare 3 Chalets in Winchendon with updated reviews, rates, and availability.

"This is a perfect location for a peaceful, lake-side getaway. The cabin was clean, well-equipped, and Jim was there to greet us and give us the lay of the land. The cabin is tucked away in a tiny cove, so you are away from the busyness of the lake, but you can still experience the amazing lake view and beautiful sunrise. (Don't forget to ask Jim about the beavers!) I highly recommend this cabin - perfect for a small family or a friends' weekend! Jim was the perfect host!"

SAR 1,270 total

includes taxes & fees

24 Sep - 25 Sep

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchendon

"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"

"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery. "

Recent reviews of Winchendon hotels

5/5 Excellent

"My stay at the Hilton Double Tree was great! I came for a work training and stayed a couple extra nights as I had some home office work to do. They were very accommodating and helpful. The cleaning staff, front desk, and restaurant staff were all wonderful. "

A verified traveler stayed at Doubletree by Hilton Hotel Leominster

Posted 2 days ago