Places to stay in Winchendon

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Popular amenities for Winchendon places to stay

Other great vacation rentals in Winchendon

Guest favorite
A rustic wooden structure is set against a vibrant blue sky, reflected in the calm waters below. The building features large windows, a clock façade, and a wraparound porch lined with potted plants, surrounded by trees showcasing autumn colors.
Home in Westminster
4.94 out of 5 average rating, 127 reviews

Wachusett Mountain Get-Away

DaeshaRating, 5 stars3 months ago
It was a pleasure staying here ! Everything is clean and the house is such a nice size !
Guest favorite
An outdoor deck area is furnished with a sectional couch featuring light-colored cushions and decorative pillows. A fire pit table sits at the center, surrounded by trees, creating a peaceful setting. A gas grill is positioned nearby, ideal for outdoor cooking.
Home in Peterborough
4.95 out of 5 average rating, 94 reviews

Hazelhurst Vacation House

ERating, 5 stars4 months ago
You walk into Eric’s place and it feels like a home thoughtfully set up so that you can just walk in and be comfortable. It’s an “and, breathe” kind of relaxing, homey place. Eric was super responsive to any & all questions we had. We absolutely loved our time there and look forward to rebooking in the future!
Guest favorite
A billiards room features a vibrant red pool table at its center, surrounded by wooden flooring. Natural light floods in through large windows, highlighting the contemporary decor. An antler chandelier hangs above, while colorful glass items are displayed on a sleek, white shelf against the wall.
Home in Bellows falls
5 out of 5 average rating, 9 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Top guest favorite
Chalet in Hillsboro
4.88 out of 5 average rating, 34 reviews

Summer time family fun at Emerald lake!

CraigRating, 5 stars2 months ago
Myself and 2 daughters loved staying at Rob's house. We went for skiing and it's very convenient to get to the local ski hills. There was plenty of space for the three of us; it was clean, cozy warm and very comfortable. Rob is very personable and responsive; loved chatting with him! We will be going back again this year if we get the chance at another ski weekend. His place is also in a prime spot for summer, something we'll consider if we decide not to do tent camping. Overall 5 stars for us.
Guest favorite
The living area features a stone fireplace and a flat-screen television mounted above. The space includes a mix of comfortable seating, such as a blue sofa and patterned armchairs. Exposed wooden beams and a spiral staircase add architectural interest to the cozy environment.
Cottage in Stow
4.95 out of 5 average rating, 171 reviews

White Pine Cottage

NickRating, 5 stars2 weeks ago
Great older lake house vibe. We liked it very much. It worked great for our family of five.
Guest favorite
The exterior of a two-story wooden home is shown, surrounded by a lush green lawn. A large tree provides shade, while the blue sky features scattered clouds. A relaxed seating area is visible on the grass, enhancing the scenic countryside setting.
Home in Putney
4.89 out of 5 average rating, 103 reviews

Peaceful Beautiful Mountain Home Spectacular Views

LibbyRating, 5 stars2 months ago
We had a wonderful stay. Very peaceful location and the views are amazing!
Superhost
An outdoor deck features a hot tub, providing a relaxing space. Comfortable seating is arranged with turquoise cushions around a central fire pit. A gas grill is positioned nearby, and a shade sail provides coverage from sunlight. The surrounding neighborhood is also visible.
Townhouse in Easthampton
4.85 out of 5 average rating, 310 reviews

In style row house with private hot tub/pool table

MarkRating, 5 stars3 months ago
Great spot - close to the little downtown area with a few restaurants and bars. Lots of room and Ginny was very responsive and clear in her communications. Would definitely stay here again.
Top guest favorite
Farm stay in Ashby
5 out of 5 average rating, 16 reviews

The Wellington House

MargeauxRating, 5 stars4 months ago
We had a wonderful stay at Sharon's place! During the winter the location was picturesque with the view of the horses and pond in the snow. The kitchen was well stocked, making it easy to prepare meals during my stay. Sharon was a great host—she was very accommodating and proactive and made sure I had everything I needed. I would highly recommend staying here!

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