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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Top guest favorite

A bright bathroom features a clawfoot bathtub, creating a focal point against the deep red walls. Natural light filters through a window, illuminating the space. Woven rugs add texture to the wooden floor, while neatly arranged towels are visible on a nearby bench.

Cottage in Petersham

4.98 out of 5 average rating, 199 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Guest favorite

A home office is shown, featuring a desk with multiple screens, a printer, and decorative items. Large sliding glass doors offer a view of Tully Pond and the surrounding trees, with a glimpse of a patio area and outdoor seating. Natural light illuminates the room.

Cottage in Orange

4.9 out of 5 average rating, 119 reviews

The Film Shack: A Sweetwater Stay

Located on the shore of Tully Pond, The Film Shack is a newly designed water front vacation home with breathtaking views of Tully Mountain. This 4-season home features four bedrooms, a screening room, a video game nook and a bonus guest cottage. The personal home of filmmakers Patti Moreno and Robert Patton-Spruill, it is decorated in the "Atomic Age" style. Maple floors, aviation, and cargo style furniture, stainless steel bathroom and kitchen with a wood stove for those chilly fall mornings.

Top guest favorite

A modern bathroom features a spacious glass shower with a sleek transparent design. A textured rug in neutral tones lies on the tiled floor, complementing the clean lines of the cabinetry nearby. Natural light may be visible, enhancing the inviting atmosphere.

Guest suite in Ashburnham

4.98 out of 5 average rating, 467 reviews

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

Top guest favorite

A charming cabin features a light blue exterior with a sloped roof and welcoming porch. Surrounded by lush greenery, landscaped flower beds with blooming white hydrangeas and evergreen bushes complement the serene setting. A spacious lawn provides ample outdoor space for relaxation.

Guesthouse in New Ipswich

4.95 out of 5 average rating, 358 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

Superhost

The interior of the cabin features vaulted wooden ceilings and warm wood paneling. A spacious seating area is arranged around a coffee table beneath an overhead light fixture. A dining table with bright red chairs is positioned nearby, with a view of the kitchen and cozy fireplace.

Cabin in Fitzwilliam

4.86 out of 5 average rating, 101 reviews

Charming Waterfront Log Cabin

Escape the daily grind at this unique & tranquil getaway. At the end of a quiet road, this vintage log cabin sits on a 150-acre pond with access to kayaks to explore at your pleasure. Inside, the space features 2 bedrooms & a spacious loft. Listen to the sounds of nature by the fire pit, watch the sunset from the porch, paddle on the pond, or watch Netflix on our fiberoptic Wi-Fi. However you slice it, you'll leave The Pond Camp relaxed, rejuvenated, & ready to tackle whatever comes your way.

Top guest favorite

A colorful hammock suspended between two trees invites relaxation. The vibrant stripes of the hammock contrast with the surrounding greenery. Bare feet rest comfortably on its edge, while the red house and lush foliage are visible in the background, creating a peaceful atmosphere.

Guesthouse in Wilton

4.95 out of 5 average rating, 644 reviews

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Top guest favorite

A red tray is positioned on a light-colored dresser, containing a remote control and a white dish labeled 'TRINKETS'. The dish provides a dedicated space for small items, enhancing organization on the dresser.

Guest suite in Hubbardston

4.99 out of 5 average rating, 124 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

Top guest favorite

A serene waterfall cascades over a stone edge, providing a soothing soundscape. Surrounded by lush greenery and autumnal trees, the scene offers a tranquil view of nature's beauty. The water flows gently into a calm body below, enhancing the peaceful ambiance of the area.

Loft in Peterborough

4.99 out of 5 average rating, 176 reviews

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Guest favorite

A night sky displays a gradient of purple and dark blue tones, with stars scattered across the expanse. Silhouettes of power lines extend from the foreground into the distance, contrasting against the celestial backdrop.

Camper/RV in Guilford

4.93 out of 5 average rating, 142 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Top guest favorite

A sleek Keurig coffee maker is positioned on a dark countertop, accompanied by a transparent kettle and a glass canister filled with coffee pods. The modern appliances are set against a neutral grey wall, adding a contemporary touch to the space.

Guesthouse in Westminster

4.98 out of 5 average rating, 397 reviews

Guest House - 4 miles from Wachusett Mt.

Welcome to a cozy, newly renovated semi-attached in-law unit! Nestled in a peaceful neighborhood, you’ll be just a short walk from the town center and only a 10-minute drive to the scenic Mount Wachusett. With easy access to Route 2, it’s the ideal base for your adventures. Enjoy the privacy of your own entrance and two dedicated parking spaces. Whether you’re here for a weekend getaway or a longer stay, we’re sure you’ll enjoy your time in this inviting space!

Guest favorite

The exterior of a wooden cabin features a vibrant blue door, complemented by large windows adorned with sheer white curtains. A picnic table with an unfinished wood finish sits in front, surrounded by a natural setting of tall trees and soft ground cover.

Cabin in Warwick

4.98 out of 5 average rating, 218 reviews

Artsy Pine Cabin in the Woods

Come relax in our private and cozy one room cabin tucked in the woods on the family homestead. A peaceful location for connecting with nature, writing & hiking. It's a 12'x16' cabin, with a comfortable queen size bed, electricity, mini refrigerator and electric kettle. Water is provided. Equipped with a clean outhouse and an outdoor hot shower on side of main house. ( May use indoor shower in main house in cooler months) Excellent spot for star gazing.

Top guest favorite

Guest suite in Peterborough

4.99 out of 5 average rating, 161 reviews

Meadow View

Enjoy this sunlit sanctuary in a 275-year-old farmhouse. Our 'in-law' suite is a cozy retreat, full of art. Adjacent to Casalis State Park, enjoy scenic trails for biking, hiking at all seasons. Enjoy Peterborough's yoga studios, coffee shops and restaurants. Meadow View offers a 750 sq ft private suite with a king-size bed, clawfoot bathtub, and a mini kitchen. Your comfort is our priority. Experience the perfect blend of historic charm and comfort.

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Popular amenities for Winchendon places to stay

Self check-in

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BBQ grill

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Wifi

Other great vacation rentals in Winchendon

Top guest favorite

Two Nigerian Dwarf goats are seen in a grassy area, showcasing their distinct markings. One goat has a dark coat with patches of white, while the other is primarily light brown with dark spots. Their playful demeanor adds a charming touch to the natural setting.

Yurt in Mason

4.98 out of 5 average rating, 55 reviews

Sweet Retreat and Yurt Farm

AshlynRating, 5 stars1 week ago

The yurt was so nice! Exactly what is pictured. We stayed the weekend for our anniversary and had a great time! We loved meeting and feeding the goats!! You don’t have to bring anything the yurt has it all!! Thank you for a great weekend!

Cottage in Ashburnham

4.89 out of 5 average rating, 131 reviews

"Trails End" Lakeside Cottage in Small Town USA

VinceRating, 5 stars1 week ago

I am beyond impressed with this location. Very appreciative of the opportunity to stay here. I have nothing but great memories now thanks to Joey. Hope to possibly come back again!

Top guest favorite

A wooden dock extends over a calm lake, reflecting the clear blue sky and lush green trees along the shoreline. The tranquil water mirrors the surrounding landscape, with gentle hills visible in the background.

Cottage in Orange

4.99 out of 5 average rating, 78 reviews

Lake House with view of mountain

JonathanRating, 5 stars8 months ago

Great Lake side cottage charm. Fully stocked kitchen. Lots of fun water toys to use. Great views and peaceful!

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 cozy sunroom features two spacious daybeds adorned with soft blankets and cushions, positioned beside large windows that offer serene views of the pond. Natural light floods the room, highlighting wooden walls and a unique stained glass window at the peak of the ceiling.

Cabin in Athol

4.97 out of 5 average rating, 76 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

JacquelineRating, 5 stars5 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 wooden dock extends into a calm lake, featuring two Adirondack chairs positioned for lake views. A kayak rests at the edge of the dock, mirrored by the still water, with trees visible along the shoreline under a clear blue sky.

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!

Guest favorite

A serene lake scene is captured, featuring clear waters reflecting the bright sky. A small sandy beach area is visible, leading to gentle waves. A boat is moored nearby, with lush greenery lining the opposite shore.

Home in Rindge

5 out of 5 average rating, 23 reviews

Changes in Attitude

AmandaRating, 5 stars3 weeks ago

My family absolutely loved staying in this cabin! It was so nice and cozy, perfect for our weekend away. The kids loved it and are already asking to go back. The host is so nice and responded quickly. She made us feel so comfortable! We would definitely stay again!

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Places to stay in Winchendon

Top-rated places to stay in Winchendon

Vacation rentals for every style

Popular amenities for Winchendon places to stay

Other great vacation rentals in Winchendon

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