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Places to stay in Winchendon

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Vacation rentals for every style

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Popular amenities for Winchendon places to stay

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Other great vacation rentals in Winchendon

Superhost
The bathroom sink features a smooth, pink basin set into a marbled countertop. Two soap dispensers are positioned to the left, offering liquid soap options for guests. The polished chrome faucets gleam under soft lighting, enhancing the clean and functional space.
Apartment in Gardner
4.77 out of 5 average rating, 30 reviews

Main Street Sanctuary - Cozy, Whimsical Workspace

LauraRating, 5 stars6 days ago
Such a great find with such short notice! Had everything we needed for the week. Andrew was a very responsive and friendly host! Will def stay here the next time I’m in Gardner.
Guest favorite
An open living space features a high ceiling with exposed wooden beams and a large wall-mounted television. A comfortable gray sectional sofa is complemented by two round coffee tables. The staircase leads to a loft area, and a dining space with a wooden table is visible through the large windows.
Home in Westminster
4.97 out of 5 average rating, 70 reviews

Our Pondside Cabin

DanielleRating, 5 stars4 weeks ago
We had a great stay. It really is minutes away from hiking trails, as well as some restaurants. It was exactly what our large group needed. We were able to prepare meals in the kitchen and ate and played board games at the large dining table. The living room area was comfy and large enough for our group to all hang out in. The place was clean and as pictured in the listing. Kathleen was also very responsive to a few questions I had while there. I'd be happy to return.
Superhost
A wooden dock extends over calm waters, framed by vibrant autumn foliage. The reflection of trees in the water enhances the natural setting, while gentle ripples create a serene atmosphere. The distant shoreline reveals additional residences amid the colorful landscape.
Cabin in New Ipswich
4.91 out of 5 average rating, 34 reviews

Bungalow

JackieRating, 5 stars2 weeks ago
Incredible and Remote place but yet not too far away from anything you need! It’s an amazing and cozy cabin! Thank you very much for the experience and weekend spent there!
Top guest favorite
A serene view of the retreat's exterior is captured from the pond, showcasing lush greenery and tall trees surrounding the inviting structure. The calm water reflects the vibrant blue sky and trees, creating a tranquil atmosphere.
Cabin in Athol
4.97 out of 5 average rating, 75 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

JacquelineRating, 5 stars3 days ago
This was exactly the quiet, peaceful retreat we were looking for. The sun porch is what sold us (we called it The Nook), and what an absolutely perfect place to sit and read together for a few days! A family of geese came to visit and we got to watch them up close. We loved kayaking on the pond too—it’s an absolutely wild body of water with tons of massive tree roots just beneath the surface, and millions of lily pads. This converted camp is beautifully decorated, clean, and spacious. Extremely relaxing retreat for two people on an anniversary trip.
Three wall-mounted dispensers are positioned in a bathroom shower, containing body wash, conditioner, and shampoo. The dispensers display clear labels for easy identification, with a modern design that complements the tiled wall behind them.
Apartment in Winchendon
4.6 out of 5 average rating, 30 reviews

Cozy Apt 1st floor 2 beds-1 bath @ Centertown

EmeliaRating, 5 stars2 weeks ago
this place was very clean and huge! the pictures doesn't do it justice. it's a nice apt with everything you need and no one bothering you. would definitely stay again!
Top guest favorite
A serene outdoor scene captures the changing foliage as vibrant colors illuminate the landscape. A clear blue sky is visible above, with a full moon hanging in the distance. A fire pit is positioned in the foreground, surrounded by neatly stacked firewood.
Guest suite in Jaffrey
5 out of 5 average rating, 62 reviews

Relax with the View at the Farm at Woodbury Hill

KimRating, 5 stars1 day ago
The view, the view, the view. Simply walking in and seeing Mt. Monadnock and all her glory was enough but there's so much more. Andy greeted us when we arrived and immediately made us feel welcome and at home. The apartment is clean, comfortable and well kept. Kitchen is gorgeous and fully equipped. And fresh eggs left in frig was such a wonderful touch. Wine on the deck is a must as the sun sets over the beautiful gardens and the mountains. We had a perfect stay and hope to come back soon.
Top guest favorite
Cottage in Jaffrey
4.97 out of 5 average rating, 32 reviews

The Boathouse - A rustic and cozy lakeside cottage

CindyRating, 5 stars2 weeks ago
This was the perfect spot for us. The cabin was all we hoped for! Everything was so clean and well thought out. We felt at home immediately! Chris always responded to our questions. Honestly, I can’t think of anything that would have made it a better stay! If you are looking for an “in the woods” experience, this is the place!
The image captures a serene lake scene, framed by trees. A boat glides across the water, reflecting the warm hues of a sunset. The sun is partially visible through the branches, casting a soft glow over the tranquil setting.
Cottage in Winchendon
4.8 out of 5 average rating, 30 reviews

Little Camp

KerriRating, 5 stars9 months ago
Can’t say enough how much we enjoy our time at the lake! This place is amazing!
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