Cummington holiday lettings

We found 72 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Cummington that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a hot tub. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Cummington

Showing deals for:30 Oct - 6 Nov

Image gallery for Sunny Chalet: woods of Ashfield

Interior
9.6 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Sunny Chalet: woods of Ashfield

Ashfield

16% off
Price is £2,141
for 7 nights, 1 chalet
£306 per night
includes taxes & fees
Sunny Chalet: woods of Ashfield

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Choose a holiday rental for your Cummington getaway

Learn about the unique charm of Cummington with a stay in a holiday home rental. This city is well-known for its shopping and restaurants. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Cummington

Are you searching for attractions to see in the city? Venture out of your cosy holiday rental and experience everything that makes Cummington a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Land of Providence (6.8 mi / 11 km)
  • Berkshire East Ski Resort (10.9 mi / 17.6 km)
  • Bousquet Ski Area (20 mi / 32.2 km)
  • Wyndhurst Golf & Club (20.8 mi / 33.4 km)
  • Jiminy Peak Mountain Resort (21.5 mi / 34.5 km)
  • Waubeeka Golf Links (22.4 mi / 36 km)

Exploring the natural features in Cummington

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Cummington. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Swift River (2.3 mi / 3.7 km)
  • Chesterfield Gorge (4.5 mi / 7.2 km)
  • Glendale Falls (8.5 mi / 13.7 km)
  • Wahconah Falls State Park (11.5 mi / 18.6 km)
  • Littleville Lake (12.6 mi / 20.2 km)
  • Deerfield River (12.6 mi / 20.3 km)

Travelling to and around Cummington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 20.5 mi (33.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 22 mi (35.3 km) away.

Frequently asked questions

What is the best area to stay in Cummington when booking a holiday rental?
When considering a holiday rental in Cummington, Massachusetts, a popular area to stay is near the charming village centre. This location offers easy access to local amenities and a welcoming community atmosphere. Cummington is known for its picturesque landscapes and outdoor activities, making it a delightful place for nature enthusiasts.

A must-visit attraction in the area is the Cummington Historical Society, where you can delve into the rich local history and discover fascinating exhibits. Additionally, the nearby Berkshire Hills provide ample opportunities for hiking and exploring the stunning natural scenery, ideal for those who enjoy the great outdoors.

In terms of properties, there are a variety of options available, ranging from quaint cottages to larger family homes, allowing visitors to find a suitable accommodation that fits their needs.
How much does it cost to rent a holiday home in Cummington?
Prices for holiday rentals in Cummington 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cummington to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cummington holiday house rentals?
You can find great discounts on house rentals in Cummington on Vrbo, 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.
Where are the best Cummington ski resort rentals?
For skiing near Cummington, the closest ski areas are found in the Berkshires, particularly at resorts like Berkshire East and Jiminy Peak, both within a reasonable drive. When looking for rentals, consider the quaint town of Charlemont, which is conveniently located for access to these ski resorts. Here, visitors can find a range of accommodation options, including rustic cabins and charming cottages that often feature amenities such as wood-burning stoves, full kitchens, and outdoor spaces superb for après-ski relaxation.

In addition, properties in nearby towns like Ashfield and Plainfield offer a serene getaway with easy access to skiing. Many of these rentals are set against a backdrop of beautiful rural scenery, providing a peaceful retreat after a day on the slopes. Expect to find amenities such as comfortable living areas, dining spaces for family meals, and sometimes even hot tubs for unwinding.

For those interested in exploring beyond skiing, the surrounding area offers hiking and beautiful views, particularly in the nearby Mohawk Trail State Forest.
What is the most popular type of holiday rental accomodation in Cummington?
In Cummington, holiday houses and cottages are the most popular types of holiday rental accommodations, with several options available throughout the area. These rentals provide a charming and spacious environment, great for families or groups seeking a peaceful retreat in the Massachusetts countryside. Most properties feature fully equipped kitchens, comfortable living areas, and outdoor spaces like decks or gardens, allowing guests to enjoy the serene natural surroundings.
Are there any family house rentals in Cummington?
In Cummington, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area is known for its scenic beauty and outdoor activities, providing a lovely environment for family gatherings. Many of these homes come equipped with spacious living areas, full kitchens, and outdoor spaces where kids can play and explore.

Visitors can enjoy the nearby attractions, including the picturesque Berkshire Hills and the charming local parks, great for picnics and leisurely strolls. Additionally, the town's proximity to cultural sites, such as art galleries and historical landmarks, adds to the experience, ensuring that families have plenty of options for both relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in Cummington?
In Cummington, there are several holiday homes available for rent that feature pools or hot tubs, making it a delightful option for those seeking relaxation. The area is known for its picturesque landscapes and tranquil atmosphere, ideal for a peaceful getaway. Many of these properties come with amenities such as private pools, spacious outdoor decks, and hot tubs, great for unwinding after a day of exploring the natural beauty of the region. Additionally, you can expect fully equipped kitchens and comfortable living spaces, which enhance the overall experience for families or groups.
Can I find long-stay holiday rentals in Cummington?
A long-stay holiday rental in Cummington 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Cummington?
In Cummington, there are several pet-friendly house rentals available, making it a great choice for travellers who wish to bring their furry companions along. The area offers a serene, rural setting with holiday homes that typically feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ideal for relaxing after a day of exploring.

The nearby Berkshires provide opportunities for outdoor activities, including hiking and nature walks, which can be enjoyed with pets. The region is known for its beautiful landscapes and quaint small towns, offering a peaceful retreat for visitors.
Are there any remote work holiday rentals in Cummington?
In Cummington, Massachusetts, there are several remote work holiday rentals available, making it a suitable option for those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as free Wi-Fi and dedicated workspaces, allowing for a productive environment while enjoying the serene surroundings.

The area is known for its picturesque landscapes and outdoor activities, providing a peaceful backdrop for remote work. Nearby attractions include scenic hiking trails and charming local shops, great for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cummington holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cummington 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 on Vrbo 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.
What are popular rental amenities in Cummington?
In Cummington, popular rental amenities include features that enhance comfort and relaxation for travellers. Many holiday rentals come equipped with fireplaces, great for cosy evenings. Outdoor spaces like decks or patios are common, allowing guests to enjoy the surrounding natural beauty. Kitchens are a standard feature, enabling visitors to prepare their own meals, while onsite parking provides convenience for those travelling by car.
When is the best time to visit Cummington for a holiday rental?
The best time to visit Cummington for a holiday rental is during the summer months, particularly in July, when the area is bustling with activity. This peak season, spanning from June to August, invites outdoor enthusiasts to explore the stunning landscapes, partake in local events, and appreciate the vibrant community spirit.

July offers warm temperatures, typically ranging from 15 to 30 degrees Celsius, making it ideal for hiking, biking, and enjoying picturesque picnics in the Great Barrington area or along the scenic trails. Visitors can engage in the beauty of the Berkshires while taking part in various cultural activities, including art festivals and farmers' markets.

For those seeking a more budget-friendly experience, consider planning your trip in December. While this month sees fewer tourists, it provides a unique opportunity to enjoy the tranquil charm of Cummington and its winter landscapes. You can take leisurely walks or simply relax in a cosy rental, embracing the peaceful atmosphere.
How early should I book a Cummington holiday rental?
Book your Cummington holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cummington?
In Cummington, visitors can explore the picturesque beauty of the Berkshire Hills. The town is known for its charming rural setting, making it a superb destination for those seeking outdoor activities. The nearby Chesterfield Gorge, part of the Massachusetts State Parks system, offers scenic hiking trails and stunning views of the natural landscape.

Cummington is also home to the historic Cummington Community House, which hosts various events and serves as a cultural hub for the local community. The area is ideal for nature enthusiasts, with opportunities for birdwatching, fishing, and enjoying the tranquil atmosphere.

For art lovers, the nearby town of Ashfield features the renowned Ashfield Lake, which is surrounded by lovely galleries and local artisan shops.
Can I change or cancel my Cummington home rental booking on Vrbo?
To find Cummington holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cummington holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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