
Places to stay in Winchendon
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Top-rated places to stay in Winchendon
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Winchendon places to stay
Other great vacation rentals in Winchendon
Top guest favorite

Home in Francestown
5 out of 5 average rating, 9 reviewsOutdoor Escape | Trails, Deck & Walk to Dining
LauraRating, 5 stars1 month ago
We loved staying the weekend at one of Zachary’s properties. It was perfect for our little get away!
Guest favorite

Home in Westminster
4.94 out of 5 average rating, 127 reviewsWachusett 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

Home in Peterborough
4.95 out of 5 average rating, 94 reviewsHazelhurst 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

Home in Newfane
4.92 out of 5 average rating, 49 reviews6 BR Perfect Private Retreat in Vermont!
AlexRating, 5 stars8 months ago
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again
Guest favorite

Cottage in Stow
4.95 out of 5 average rating, 171 reviewsWhite Pine Cottage
NickRating, 5 stars1 week ago
Great older lake house vibe. We liked it very much. It worked great for our family of five.
Guest favorite

Home in Putney
4.89 out of 5 average rating, 103 reviewsPeaceful Beautiful Mountain Home Spectacular Views
LibbyRating, 5 stars2 months ago
We had a wonderful stay. Very peaceful location and the views are amazing!
Superhost

Townhouse in Easthampton
4.85 out of 5 average rating, 310 reviewsIn 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 reviewsThe 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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