Holiday rentals in Dalton

Downtown Apartment A

Centrally located in the Berkshires. Enjoy a beautiful day at Tanglewood, view the amazing art at Mass Moca or discover nature on one of the many hiking/biking trails the Berkshires has to offer. Located 5 mins from Bousquet and close to Jimmy Peak as well for anyone enjoying the snow! There are a variety of delicious restaurants to suit any appetite. Located in a quiet neighborhood, if your out & about all day or just looking to get away from the hustle & bustle of the city it's a perfect spot.

Value · Family · Long stay

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.

Location · Family · Decor

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

Location · Family · Hot tub

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Value · Location · View

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.

Value · Family · Air conditioning

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!

Location · Value · TV

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!

Location · Value · Skiing

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.

Location · Value · TV

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.

Family · Location · Nearby

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.

Family · Location · Amenities

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 .

Location · Family · Shared spaces

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.

Family · Value · Condition