Vacation rentals in Dalton

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Top-rated vacation rentals in Dalton

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Top guest favorite

A serene lakefront property is viewed from the water, featuring a well-maintained lawn and inviting home. The structure is flanked by mature trees, while a small private dock extends into the lake, providing easy access to the water.

Home in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

Stunning lakefront property on 1-acre on Pontsoosuc Lake in western MA, in the heart of the Berkshires. This beautiful home features 3 bdrms & 2.5 baths. A large primary suite (king bed) sits on one side of the home, w/ two guest bdrms (king bed, queen bed) on the other end of the house. Kitchen, dining, and living room areas are spacious and open, with high ceilings & skylights. Cozy closed-in lakeside backporch opens to a small back deck. Large front side porch is set back from main road.

5.0 out of 5 average rating, 26 reviews

Superhost

Home in Dalton

Little Yellow House!

The Little Yellow House is a charming and cozy open concept 1Bd/1Bth, built in 1900. Hardwood floors and vaulted ceilings create a stylish spacious feel. Renovated kitchen w/new appliances. Updated bathroom w/new shower. Upstairs loft bedroom w/ built-in storage and integrated bookshelves. The couch features a fold out premium mattress. Your private outdoor oasis features a deck, patio and grill. Walkable to downtown Dalton restaurants, the Appalachian Trail, nearby Wahconah Falls State Park.

4.86 out of 5 average rating, 7 reviews

Guest favorite

A tranquil lakeside scene is depicted, showcasing a wooden dock reflecting in the calm water. Surrounding trees exhibit vibrant autumn colors, and a gazebo is situated on the shoreline, offering a serene retreat amidst nature.

Apartment in Hinsdale

Lakeside Getaway

Lakeside respite awaits you in this comfortable getaway by the lake. Easy access to major Berkshire attractions, but tucked out of the way. Private patio includes a fire pit and view to the lake. Enjoy an easy walk to our private docks with kayaks available for renters. The guest suite includes a bedroom with a queen-sized bed, a sitting room with an optional floor mattress, eat-in counter and kitchenette, and a full bath. The suite has a private entrance and is locked off from the main house.

4.97 out of 5 average rating, 31 reviews

Top guest favorite

A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.

Cottage in Hinsdale

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

4.99 out of 5 average rating, 168 reviews

Top guest favorite

An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.

Home in Dalton

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

4.93 out of 5 average rating, 211 reviews

Top guest favorite

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.95 out of 5 average rating, 232 reviews

Guest favorite

A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

4.85 out of 5 average rating, 300 reviews

Top guest favorite

Home in Hinsdale

Hummingbird Haven

Welcome to Hummingbird Haven, a bright and spacious 4–5 bedroom home in the heart of the Berkshires. With 3,100 sq. ft., high ceilings, and a cozy loft, it’s perfect for relaxing getaways in every season. Ideal for families, professionals, or friends, this inviting home offers comfort, charm, and room to connect. Enjoy nearby trails, lakes, beaches, ski resorts, and local arts—or stay in and unwind with games, a stocked kitchen, and sunlit spaces. A peaceful escape minutes from it all.

5.0 out of 5 average rating, 19 reviews

Top guest favorite

A modern two-story house features a combination of blue siding and natural wood accents. Large windows provide ample natural light, while a stone pathway leads to the main entrance. Lush greenery surrounds the home, complemented by landscaping that enhances its contemporary design.

Home in Hinsdale

Modern Lakehouse with Private Lake Access

Clean style and calming stay, this is an all-season home with private access to Lake Ashmere - a hidden gem within the Berkshires boasting frequent activity yet remaining private and tranquil. Enjoy the summer water, fall foliage, or winter ice depending on when you stay. The home is located with easy access to various other Berkshire amenities such as Jiminy Peak, Bousquet Mountain, golf courses, hiking trails, along with being only 25 minutes from locations such as downtown Lenox.

4.97 out of 5 average rating, 31 reviews

Guest favorite

The exterior of a renovated antique farmhouse is displayed, featuring a white facade and multiple entrances framed by greenery. A spacious lawn surrounds the house, complemented by mature trees in the background under a clear blue sky.

Home in Lanesborough

Elmwood Farmhouse

Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. The house is spacious and welcoming with a sunny deck and welcoming porch. Dog friendly with a fully enclosed yard. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, and other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Ashuwilticook Bike Trail is across the street. Whitney's Farm stand nearby with fresh Produce and Deli .

4.9 out of 5 average rating, 124 reviews

Guest favorite

A two-story house features a welcoming front porch with white railings and multiple planters. Red shutters adorn the windows, complementing the light-colored siding. A well-maintained lawn stretches in front, bordered by a path leading to the entrance. The setting reflects a pleasant neighborhood atmosphere.

Apartment in Dalton

1843 House - Bright and Airy 5 Rooms (2 Bedrooms)

Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, linens and extra blankets. Nice front and back porches. Plenty of parking. Centrally located in the beautiful Berkshires, a short drive to anything. The stairs are very quirky and not for the faint at heart. You'll love them or hate them! See picture. ***NOTE: We are family-friendly! We make an extra effort to ensure that children and pets feel welcome and are comfortable.

4.9 out of 5 average rating, 21 reviews

Top guest favorite

A charming red farmhouse is framed by lush greenery, showcasing a two-story structure with multiple gabled roofs and large windows. A gravel pathway leads up to the front porch, which features seating, while a garage is visible to one side.

Farm stay in Dalton

Gorgeous Working Farm in the Berkshires

Get away from it all when you stay on our beautiful 4th generation working farm. Farmhouse backs up to 1000 acres of woodlands with trails, brooks and small bodies of water. See farm animals out grazing in the fields while you get cozy in our 5 bedroom farmhouse. Toast marshmallows over a campfire, walk the many roads and trails, or just sip some wine on the porch and enjoy the clean air and delightful views. Night skies are breathtaking on a clear evening.

5.0 out of 5 average rating, 20 reviews