Places to stay in Winchendon

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Popular amenities for Winchendon places to stay

Other great vacation rentals in Winchendon

Top guest favorite
The bedroom features a spacious bed with soft linens, complemented by decorative pillows. A cozy fireplace is situated beneath a framed landscape painting. Light filters through the striped wooden blinds covering the double doors, which open to a private outdoor space.
Home in Francestown
5 out of 5 average rating, 9 reviews

Outdoor 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
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
The spacious outdoor deck surrounds a circular swimming pool, inviting relaxation under the sky. A red railing complements the vibrant blue water. The two-story house, featuring large windows, stands in the background, framed by lush greenery and a clear blue sky.
Home in Newfane
4.92 out of 5 average rating, 49 reviews

6 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
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 stars1 week ago
Great older lake house vibe. We liked it very much. It worked great for our family of five.
Guest favorite
The exterior view of the house showcases a two-story wooden structure with large windows that allow for natural light. Two Adirondack chairs are positioned on the grassy lawn, creating a peaceful area for relaxation. A wood pile is stacked beneath a covered area at the side of the house.
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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