Vacation rentals in Dalton

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Top-rated vacation rentals in Dalton

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Top guest favorite

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 184 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Top guest favorite

An open door reveals the entryway of a rustic cabin. A patterned rug leads into a softly lit interior, where a cozy bed is visible in the background, framed by natural wood accents and windows that invite the outside in.

Cabin in Cummington

4.98 out of 5 average rating, 213 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Top guest favorite

Cottage in Hinsdale

4.99 out of 5 average rating, 154 reviews

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.

Top guest favorite

A well-appointed kitchen features modern appliances, including a stainless-steel stove and a compact refrigerator. Wooden beams add character to the ceiling, while natural light enters through a glass-paned door. A propane stove is positioned in the corner, contributing to the cozy ambiance.

Home in Dalton

4.99 out of 5 average rating, 155 reviews

Cleveland House - renovated Berkshires' gem.

Enjoy a retreat in a home full of history - it was a tavern/stage coach stop in the 1800's. Today we have added modern comfort while keeping the charm. We are centrally located in the Berkshires making it easy to enjoy -ski Jiminy, hike Mt. Greylock, and enjoy the culture. Or stay in and unwind. Play games on the flat 3-acre yard or try yoga surrounded by nature. Work remotely in our library. Walk down our country road and enjoy the farms. Most of all, reconnect with family/friends.

Guest favorite

Home in Dalton

4.93 out of 5 average rating, 194 reviews

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!

Guest favorite

Home in Pittsfield

4.95 out of 5 average rating, 174 reviews

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!

Superhost

A weathered wooden bench is positioned amidst green grass and ornamental plants. A decorative pillow with a patterned design is placed on one side of the bench, enhancing the outdoor seating area.

Home in Dalton

4.89 out of 5 average rating, 144 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Guest favorite

A quaint cottage is nestled among trees, featuring a welcoming front porch with several potted plants and outdoor seating. The light-colored exterior is complemented by blue accents on the chairs, while the wooden deck extends invitingly, creating a serene outdoor space.

Cabin in Cheshire

4.89 out of 5 average rating, 164 reviews

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 271 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Guest favorite

Cottage in Lanesborough

4.84 out of 5 average rating, 279 reviews

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Top guest favorite

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

4.99 out of 5 average rating, 218 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guest favorite

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

4.93 out of 5 average rating, 375 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

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Popular amenities for Dalton vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Dalton

Guest favorite

A well-lit bathroom features blue floral accents on the shower curtain, complemented by a neutral tiled backdrop. Soft lighting is provided by an overhead light fixture with three bulbs. A pair of decorative towels is hung on a rail next to a white toilet, and artwork adorns the wall.

Apartment in Pittsfield

4.9 out of 5 average rating, 21 reviews

Green 2 bedroom Downtown

FabioRating, 5 stars2 weeks ago

I highly recommend the house.

Guest favorite

An open-concept living space features a wooden bar with high stools, set against a backdrop of a stone fireplace. Natural light fills the area, highlighting the exposed wooden beams in the ceiling and creating a warm, cozy environment.

Cabin in Windsor

4.9 out of 5 average rating, 10 reviews

Stone cabin in the Berkshires

JenniferRating, 5 stars4 days ago

This stone cabin in the woods is a great place to decompress and read a book, or write a book. The space is comfortable and cozy, with beautiful indoor and outdoor areas. Irene is a great host—she guided us through finding the place and answered questions promptly, but mostly left us alone to enjoy the beautiful surroundings. The cabin is quiet and in the woods, but within easy striking distance is excellent restaurants—shout out to the chocolate chip pancakes at M&Js in Adams.

Guest favorite

A cozy corner is displayed with a single padded chair beside a potted plant. Two windows allow natural light to enter, adorned with light, sheer curtains. The small space features a neutral color palette and reflects a minimalist design.

Apartment in Adams

5 out of 5 average rating, 6 reviews

Guestrooms on the Bike Trail

NicoleRating, 5 stars2 months ago

My stay at Yina's was perfect for what I was looking for. The space was cozy and quiet and that bed was so comfortable. There was a nice work space with a refrigerator as well which was convenient. Yina and Katelynn were quick to respond to messages etc.

Top guest favorite

A serene view of Lake Ashmere is presented, with a vibrant sunset illuminating the sky in shades of pink and purple. Silhouetted trees line the water's edge, reflecting softly on the calm surface of the lake.

Home in Hinsdale

5 out of 5 average rating, 14 reviews

Modern Lakehouse with Private Lake Access

TimRating, 5 stars2 weeks ago

Kasie & Anthony’s place was truly special. The home is brand new, spacious, and beautifully designed with high-end appliances and modern bathrooms. The lake view is absolutely stunning—especially from the Peloton, which made workouts feel serene. We loved the outdoor space, complete with games, patio furniture, and a cozy fire pit that brought everyone together. It was the perfect setting to celebrate my grandfather’s birthday with family and friends. Kasie & Anthony were incredibly kind and accommodating—they even helped us with the rowboat so we could enjoy the lake. Their hospitality made us feel right at home. This was more than just a stay—it was a memorable experience. Highly recommend!

Top guest favorite

An A-frame cabin is illuminated at night, featuring warm string lights adorning its exterior. A wooden deck extends from the cabin, accompanied by a picnic table positioned on the ground level. The surrounding environment exhibits a tranquil forest ambiance.

Cabin in Becket

5 out of 5 average rating, 5 reviews

WALK to lake! Dog friendly, A-Frame in Berkshires!

AustinRating, 5 stars1 week ago

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

Top guest favorite

A modern cabin features a striking facade with large windows, surrounded by colorful trees. An outdoor deck contains multiple seating areas, including lounge chairs and a dining table. A wood-fired hot tub is situated nearby, surrounded by landscaped greenery and gravel pathways.

Cabin in East Nassau

5 out of 5 average rating, 45 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

ElaineRating, 5 stars2 weeks ago

Matt and Sarah’s place is wonderful. A great place to relax and enjoy the beautiful surroundings. The house is just as described and the hosts make you feel right at home. We hope to come back again!

Superhost

A serene river flows through a forested area, framed by tall trees and lush greenery. Rocky formations dot the riverbank, and smooth stones can be seen submerged in the clear water. Sunlight filters through the leaves, creating a peaceful ambiance.

Home in Cheshire

4.93 out of 5 average rating, 73 reviews

Berkshire County modern home + pool

DanielaRating, 5 stars4 days ago

Kelsey is flexible and responsive. You can tell she thought about how to curate a great stay by all of the amenities and presentation of the house. It’s cozy! Kelsey does have house rules but they’re not overbearing and if anything it was nice to have clear expectations communicated from the beginning.

Superhost

A serene landscape features a pond surrounded by lush greenery, including trees and shrubs. The clear blue sky reflects in the water, adding to the tranquil atmosphere. Notable wildlife habitat, such as grasses and reeds, is also visible along the pond's edge.

Farm stay in New Lebanon

4.86 out of 5 average rating, 29 reviews

1800s Carriage house in Berkshires / Hudson Valley

KarenRating, 5 stars3 weeks ago

A lovely spot with a well maintained, extremely clean, spacious apartment. It was very well appointed, especially the kitchen and bathroom. Anything you needed was there. Great bed and comfortable furniture. Close to a few good restaurants and a wonderful farmers market. I would return in a minute.

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Vacation rentals in Dalton

Top-rated vacation rentals in Dalton

Vacation rentals for every style

Popular amenities for Dalton vacation rentals

Other great vacation rentals in Dalton

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