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 wrap-around porch features wooden flooring, providing a view of the surrounding nature. Tall trees and grassy areas are visible, with a blue sky dotted with clouds creating a serene backdrop. A peacock can be spotted in the distance, adding charm to the scene.

Farm stay in Mont Vernon

5 out of 5 average rating, 16 reviews

Zen Haven Farm Dog Paradise! A True Zen Escape!

A modern farmhouse with a vintage twist DOG PARADISE! FARM STAY! TRANQUIL! Welcome to Zen Haven, a pet friendly retreat on 15 acres of land in the heart of nature. We are located in Mont Vernon, NH. Embrace tranquility, unwind, and create lasting memories in this pet-friendly haven. With its perfect blend of comfort, style, and pet-friendly amenities, Zen Haven is the ideal destination for those seeking a peaceful escape. This gorgeous property shares its grounds with our charming duck barn!

Guest favorite

An outdoor deck is presented with a wooden surface, featuring several white lounge chairs positioned for relaxation. A table with chairs and an umbrella is seen in the background, providing a shaded seating area, while trees are visible in the distance.

Home in Hawley

4.93 out of 5 average rating, 15 reviews

Berkshire Basecamp: Hike, Bike, Raft & Relax!

Welcome to our cozy retreat nestled in the picturesque Berkshires, where relaxation meets adventure! Perfectly situated near prime mountain biking trails, orchards, breweries, white water rafting and hiking! Our property features a scenic meadow and historic trees, with local wildlife including hummingbirds, ravens, blue jays, and rabbits. Perfectly situated just 9 minutes from Berkshire East Mountain Resort. The cabin combines rustic charm with modern comforts, ensuring a relaxing stay.

Guest favorite

A cozy sleeping area features a plush bed adorned with several decorative pillows and a soft white duvet. Natural light enters through two small windows, highlighting the warm wooden floor. A bedside table holds a small vase with fresh flowers, adding a touch of elegance.

Cottage in Amherst

4.93 out of 5 average rating, 162 reviews

Beautifully Restored Cottage Studio

Originally built as an artist's studio, our Private Cottage is a fully-restored, light-filled, wonderfully serene space - with plush and thoughtful designer-appointed furnishings, cathedral ceilings, hardwood floors, a renovated en-suite bath, and a complete kitchen. Freshly laundered 450+ thread count Egyptian cotton beddings, linens, and towels are provided on-site as are complimentary amenities. * Fully Private, Quiet & Serene, Family-Friendly * An easy 3-minute drive to town

Guest favorite

A spacious interior is displayed, featuring a living area with comfortable seating and two beds. Large windows allow natural light to fill the space, enhancing the inviting atmosphere. Decor elements include artwork and cozy textiles, creating a homely environment suitable for relaxation.

Guest suite in Charlemont

4.91 out of 5 average rating, 208 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Top guest favorite

A modern cabin is situated among snow-covered trees, showcasing large windows that reflect the evening sky. The triangular roofline and dark exterior contrast with the white snow, while a cozy glow emanates from within.

Home in Peru

5 out of 5 average rating, 10 reviews

Highland Haus: stunning ski getaway with hot tub

Welcome to The Highland Haus! A brand new, custom luxury escape central to dining, shopping, and four Vermont ski resorts. Overlooking several mountain ranges, this high-end getaway offers an unparalleled experience in the heart of the Green Mountains: breathtaking views, three bedrooms 3.5 bathrooms, open concept living and dining rooms, outdoor dining and lounge deck, hot tub, modern decor and amenities. Come enjoy Vermont at its finest! Pets welcome with a $100 pet fee.

Top guest favorite

A staircase leading downward is showcased, featuring dark wooden steps with a carpet runner. The walls are painted in a soft grey tone. A white door at the bottom leads outside, framed by a welcoming light fixture above. A small welcome mat is positioned at the entrance.

Apartment in Northampton

5 out of 5 average rating, 45 reviews

Downtown 2 BR 1.5 Bath Townhouse Retreat 3 beds

Conveniently located townhouse that is a short walk to restaurants and shops. Easy access to public transportation with a bus stop by the end of the street. Wi-Fi, a full kitchen, living room, 1/2 bath and laundry, on the first floor. The second floor has a shower, bedroom #1 has a queen bed and bedroom #2 has a queen and a twin. A/C units during summer months. Off street parking and self check in. Pack n play and toddler bed available upon request.

Guest favorite

Home in Chester

4.92 out of 5 average rating, 191 reviews

Charming New England Farmhouse

This rustic New England Farmhouse (Recently listed as one of “The best Airbnb’s in New England” by Timeout!) has all the charm of an 18th century home, complete with all the amenities you need for your next getaway or vacation! With a sprawling yard, a newly renovated kitchen (great for gatherings), a massive deck, and 5 bedrooms. Our home has room for a fun family getaway or a relaxing retreat away from the city.

Guest favorite

The exterior of the cottage is illuminated in warm tones at dusk, showcasing traditional shingles and multiple windows. A welcoming front door is framed by plants, while nearby outdoor seating and a subtle garden are present. The ambiance is enhanced by soft lighting, creating an inviting evening scene.

Guest suite in Concord

4.96 out of 5 average rating, 249 reviews

Bright ‘n Cozy Cottage in Concord

The Cottage is attached to our 1880 New Englander. We live right next door to the Cottage with our two pups. You will have the entire guest suite to yourself. Enter through the door off of the deck. The kitchen and living room are on the first floor and the bathroom is located between the first and second floors. One bedroom has a full-size mattress and the other has two twin beds.

Top guest favorite

A screened porch offers a serene view of the surrounding landscape, with a turquoise swing positioned for relaxation. Natural light brightens the space, enhanced by the blue ceiling and wooden flooring.

Guesthouse in Framingham

5 out of 5 average rating, 11 reviews

Enchanted Cottage on 5 Acres

Keep it simple at this peaceful and centrally-located place, a unique guest cottage located in a picturesque field. You won't believe it until you see it! the perfect little dream house that feels like being in the English countryside. Comfortably decorated and offers a fully equipped kitchen to meet your needs. There are two bedrooms upstairs and a full bath on each floor.

Guest favorite

A spacious interior features warm wooden accents, including a large barn door that leads to another area. The dining table is positioned along one side, and a mirror reflects light from the softly illuminated ceiling. The open design connects to the kitchen area in the background.

Home in Dover

5 out of 5 average rating, 5 reviews

Riverside Home On Route 100 (Moover Bus Stop)

Come stay at our newly renovated VT Route 100 getaway on the Deerfield River. We’re passionate about creating simple, thoughtfully designed homey spaces that make for the perfect retreat to Mount Snow. Located on the Moover route, just north of Snow Republic Brewery and next to High Altitude Ski Rental, this no-stairs unit offers convenience and charm in equal measure.

Top guest favorite

An outdoor space features a grassy area surrounded by trees, with wooden decking highlighted in the foreground. Two black chairs are positioned on the deck, while a children's playground structure and a shed are visible in the background.

Guest suite in Whitinsville

5 out of 5 average rating, 11 reviews

Adorable 1-bedroom suite with off-street parking

Come stay in comfort at this charming 1-Bedroom suite with off street parking and a private entrance. Additional queen bed and futon in the main living area to accommodate extra guests. The whole place was just freshly painted to brighten up your stay. Book your stay today!