Dalton holiday rentals

We found 438 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Dalton that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Dalton

Showing deals for:11 Dec - 18 Dec

View from the lawn by the water
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$6,728
for 7 nights, 1 home
AU$961 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
View from entry into living room- perfect spot for relaxing!
Kitchen with counter seating for 4- door on the right to garage
Property grounds
Enclosed porch- view into back yard- dining/game table
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,210
for 7 nights, 1 home
AU$744 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Room
Terrace/patio
Private kitchen
Dining
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
AU$4,018
for 7 nights, 1 cottage
AU$574 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Outdoor dining
Living area
Interior
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$5,787
for 7 nights, 1 home
AU$827 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Reading nook with natural lighting
Fully screened porch!
Dining Room w/ Doors to Screened Porch Dining Area
Kitchen with stainless steel appliances
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$4,176
for 7 nights, 1 home
AU$597 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Dining
Interior
Exterior
Living area
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,712
for 7 nights, 1 cabin
AU$530 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Property grounds
Outdoor dining
Renovated kitchen
Dining
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

21% off
AU$5,325
for 7 nights, 1 home
AU$761 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Entrance into house with wood burning stove to right and staircase
View from 2nd floor balcony (after leaves have fallen)
Views from the back of the 16 acres on the property
Large Smart HDTV with electric fireplace in living room, showing dining room
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
AU$3,206
for 7 nights, 1 home
AU$458 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
Spring at Jiminy Peak 2019
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Interior
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
AU$7,664
for 7 nights, 1 home
AU$1,095 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Exterior
BBQ dinner not included :)
Interior
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

8% off
AU$4,977
for 7 nights, 1 home
AU$711 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Beaver Pond Pool/clubhouse
new backyard table
another view of same bedroom as well as makeup table
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

23% off
AU$4,958
for 7 nights, 1 apartment
AU$708 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Heidi visiting Jane's 18th Century Studio
Interior
Interior
Interior
Exceptional
(99 reviews)

19th c. Barn in the Berkshires

Cheshire

8% off
AU$3,917
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
19th c. Barn in the Berkshires
Living Room, wow!
Dining
view into large bathroom
Entry and living room
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,426
for 7 nights, 1 apartment
AU$489 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior
Interior
Room
Bathroom
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
AU$3,768
for 7 nights, 1 home
AU$538 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Private kitchen
Lobby
Room
Outdoor dining
Exceptional
(6 reviews)

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

West Stockbridge

8% off
AU$4,356
for 7 nights, 1 home
AU$622 per night
includes taxes & fees
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
Quarter & Rift sawn white oak floors
Private kitchen
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Dining
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
AU$6,201
for 7 nights, 1 apartment
AU$886 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the natural setting in Dalton

Enjoy the museums and other features of Dalton. One of the city's many top draws is its parks. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Dalton

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Dalton a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (7.1 mi / 11.4 km)
  • Jiminy Peak Mountain Resort (8.5 mi / 13.7 km)
  • Kennedy Park (8.6 mi / 13.8 km)
  • Wyndhurst Golf & Club (10.4 mi / 16.7 km)
  • Waubeeka Golf Links (13.2 mi / 21.3 km)
  • Berkshire East Ski Resort (17.9 mi / 28.8 km)

Exploring the natural landscape of Dalton

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Dalton is a great place to get out in nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Wahconah Falls State Park (2.8 mi / 4.5 km)
  • Pontoosuc Lake (4.5 mi / 7.2 km)
  • Mount Greylock State Reservation Visitor Center (6 mi / 9.7 km)
  • Kennedy Park (8.6 mi / 13.8 km)
  • Lenox Mountain (8.7 mi / 14 km)
  • The Mount (11.2 mi / 18.1 km)

Transport options to and around Dalton

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 7.2 mi (11.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 30.5 mi (49.1 km) away.

Frequently asked questions

What is the best area to stay in Dalton when booking a holiday rental?
When considering a holiday rental in Dalton, Massachusetts, a popular area to stay is near the charming downtown district. This area boasts a variety of rental properties, ranging from cosy cottages to comfortable apartments, providing visitors with a range of options to suit their preferences.Staying in the downtown area allows easy access to local attractions, such as the picturesque Oak Hill Park, which offers beautiful walking trails and picnic spots superb for enjoying the natural beauty of the region. Additionally, the nearby Berkshire Museum in Pittsfield, just a short drive away, provides an excellent opportunity to explore art, science, and history, making it a great day trip for families.Another appealing option is the neighbourhood surrounding the scenic Berkshire Hills, which is renowned for its stunning landscapes and outdoor activities. Here, you can find a selection of properties located amidst nature, ideal for those looking to unwind and enjoy hiking or simply taking in the breathtaking views.
What is the most popular type of holiday rental accomodation in Dalton?
In Dalton, holiday houses are the most popular type of holiday rental, with several available across the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable home base. Many also come with outdoor spaces, such as patios or gardens, superb for enjoying the fresh air after a day of exploring the nearby attractions. Additionally, several apartments and cottages can be found, offering a more intimate setting for couples or solo travellers.
Are there any family house rentals in Dalton?
In Dalton, Massachusetts, there are some family-friendly house rentals available, making it an excellent choice for those travelling with children. The town features charming homes that often include spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where kids can play safely.Visitors will appreciate the convenient access to nearby attractions such as the picturesque Berkshire Mountains, great for outdoor adventures, hiking, and enjoying nature. Additionally, the local parks offer playgrounds and picnic spots, enhancing the family-friendly experience.
Are there pet-friendly house rentals in Dalton?
In Dalton, there are several pet-friendly house rentals available, offering a great option for travellers looking to bring their furry companions along. The area features homes equipped with various amenities, such as fully stocked kitchens, comfortable living spaces, and outdoor areas where pets can play. Many properties also include features like fenced yards or patios, which provide a safe environment for pets to enjoy the outdoors.The charming surroundings of Dalton offer access to nearby parks and green spaces, ideal for walks and outdoor activities with pets. The town's close-knit community feel adds to the appeal, making it a welcoming destination for families and pet owners alike.
Are there any remote work holiday rentals in Dalton?
In Dalton, Massachusetts, there are several holiday rentals available that cater to remote work needs. Many of these properties feature Wi-Fi, ensuring that guests can stay connected while working from the comfort of their accommodation. Expect amenities such as dedicated workspaces or areas designed for productivity, alongside comfortable living spaces that allow for relaxation after a day of work.The town is set against a backdrop of beautiful landscapes, providing opportunities for outdoor activities during breaks. Additionally, Dalton's proximity to the vibrant cultural offerings of the Berkshires enhances the appeal for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Dalton?
In Dalton, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy the comforts of home. Many rentals also feature a coffee and tea maker for those early morning brews. For those travelling with pets, several properties permit them, making it easier for pet owners to enjoy their stay. Additionally, some rentals provide a selection of books, great for guests looking to unwind with a good read after a day of exploring the area. A blender is also commonly available, suiting those who enjoy smoothies or cooking at home.
When is the best time to visit Dalton for a holiday rental?
The most popular time to visit Dalton is during the summer months, particularly in July, when the area comes alive with vibrant outdoor activities and events. This peak season, spanning from June to August, attracts many travellers eager to enjoy the stunning natural beauty of the Berkshires, alongside a variety of cultural offerings such as local festivals and outdoor concerts.During July, visitors can revel in warm temperatures, often reaching the mid to high 20s Celsius, making it an ideal time for hiking, biking, and exploring the picturesque landscapes. The lush greenery and blooming flowers provide a beautiful backdrop for sightseeing, whether you're wandering through local parks or taking in the views from nearby Mount Greylock.For those considering a more budget-friendly option, December can be a delightful time to experience Dalton's charm without the summer crowds. The winter season brings its own unique beauty, with opportunities for cosy indoor activities, holiday events, and perhaps a chance to enjoy the first snows of the year.Ultimately, your choice of when to visit Dalton will depend on whether you prefer the lively option of summer adventures or the serene beauty of wintertime exploration.
What are the top attractions in Dalton?
In Dalton, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The picturesque Berkshire Hills provide ample opportunities for outdoor activities, including hiking and biking, with several trails accessible from the town.One popular point of interest is the Ashuwillticook Rail Trail, a scenic path superb for walking and cycling, which stretches through lush landscapes and offers views of the surrounding countryside. Additionally, the nearby Pittsfield State Forest, located just a short drive away, features extensive hiking trails and picnic areas, making it an excellent spot for nature lovers.For those interested in local culture, Dalton also hosts events and activities at its community parks and recreational facilities, fostering a sense of community.
Are all fees included in the Dalton holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Dalton holiday homes with parking?
Stayz offers a wide selection of holiday homes in Dalton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Dalton holiday homes?
You can find great discounts on holiday homes in Dalton on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Dalton holiday home booking on Stayz?
To find Dalton holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Dalton?
A long-stay holiday home in Dalton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Dalton holiday home?
Book your Dalton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Dalton?
Prices for holiday homes in Dalton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Dalton to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.