Charlemont holiday rentals

We found 138 holiday rentals — enter your dates for availability
Discover a selection of 13 homes and other holiday rentals in Charlemont that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, including air conditioning and cable TV. 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 – Charlemont

Showing deals for:18 Dec - 25 Dec

Property grounds
Interior
Dining
Living area
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
AU$4,416
for 7 nights, 1 chalet
AU$631 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
Dining
Pool
Exterior
Modern kitchen with Viking stove and extensive collection of pots and pans.
Exceptional
(8 reviews)

1770 House - An end of a dirt road hideaway where you can relax and unwind.

Colrain

8% off
AU$9,294
for 7 nights, 1 home
AU$1,328 per night
includes taxes & fees
1770 House - An end of a dirt road hideaway where you can relax and unwind.
Property grounds
Outdoor dining
Living area
Living area
Exceptional
(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off
AU$3,519
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Private kitchen
Private kitchen
Living area
Interior
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
AU$3,704
for 7 nights, 1 home
AU$529 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Room
Owner and guest parking. Private guest access is located through the porch door.
A small kitchenette fully equipped for small-scale cooking.
Hallway view from the bathroom looking toward the kitchen area.
Exceptional
(35 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
AU$1,372
for 7 nights, 1 apartment
AU$196 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Interior
Living area
The cottage garden in full summer bloom
Room
Exceptional
(211 reviews)

Amazing People & Pet-Welcoming Country Haven

Charlemont

9% off
AU$1,891
for 7 nights, 1 room
AU$270 per night
includes taxes & fees
Amazing People & Pet-Welcoming Country Haven
Living room
MassMoCA in nearby North Adams, Mass
fire pit
Exterior
Exceptional
(13 reviews)

Family Home in the mountains. Get out and explore!

Monroe

16% off
AU$1,776
for 7 nights, 1 home
AU$254 per night
includes taxes & fees
Family Home in the mountains. Get out and explore!
Living area
Interior
Interior
Exterior
Exceptional
(97 reviews)

The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome

whitingham

11% off
AU$2,433
for 7 nights, 1 home
AU$348 per night
includes taxes & fees
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
Spiral stairs to the 2nd floor could be tricky for people with mobility issues.
First Floor, Passive Solar Porch
Living Room Wood Stove area
Fallscape with Pond and Dog
Exceptional
(43 reviews)

A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View

Ashfield

12% off
AU$3,365
for 7 nights, 1 home
AU$481 per night
includes taxes & fees
A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View
Room
Living area
Games room
Bathroom
Very good
(5 reviews)

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Whitingham

8% off
AU$4,151
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Explore the natural setting in Charlemont

Enjoy the monuments and other features of Charlemont. This city is well-known for its skiing and 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.

Activities and attractions in Charlemont

Do you want to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that Charlemont has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Berkshire East Ski Resort (0.8 mi / 1.3 km)
  • The Hermitage Golf Club (18.8 mi / 30.2 km)
  • Waubeeka Golf Links (18.9 mi / 30.4 km)
  • Prospect Mountain Cross-Country Ski Center (19.9 mi / 32.1 km)
  • The Hermitage Club (20.5 mi / 33 km)
  • Mount Snow Golf Course (21.4 mi / 34.4 km)

Exploring the natural landscape of Charlemont

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Charlemont is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Deerfield River (6.8 mi / 10.9 km)
  • High Ledges Wildlife Sanctuary (7.6 mi / 12.2 km)
  • Bullitt Reservation (10.5 mi / 16.8 km)
  • Windsor Lake Park (12.1 mi / 19.5 km)
  • Jacksonville Pond (12.2 mi / 19.6 km)
  • Harriman Reservoir (13.9 mi / 22.4 km)

How to get to and around Charlemont

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 25.6 mi (41.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 32.7 mi (52.6 km) away.

Frequently asked questions

What is the best area to stay in Charlemont when booking a holiday rental?
When considering a holiday rental in Charlemont, Massachusetts, the Charlemont area itself is an excellent choice due to its stunning natural surroundings and a range of outdoor activities. This charming town is located in the picturesque Berkshires and is renowned for its beautiful landscapes, making it great for those who appreciate nature.In Charlemont, you'll find a variety of properties available for rent, suiting different preferences and budgets. The area is particularly popular among outdoor enthusiasts, with attractions such as the renowned Mohawk Trail, which offers breathtaking views and opportunities for hiking, cycling, and exploring. Additionally, the nearby Berkshire East Mountain Resort is a fantastic destination for skiing in winter and mountain biking in the warmer months, providing year-round outdoor fun.Staying in Charlemont allows you to soak in the tranquil atmosphere while being close to a range of activities. The local dining scene also reflects the area's charm, with several eateries offering delicious, locally sourced fare.
Where are the best Charlemont ski resort rentals?
For those looking to rent accommodation near the Charlemont ski area, the town itself offers a quaint New England charm with a range of options. Many visitors choose to stay in the nearby village of Charlemont, where you can find cosy cabins and chalets that cater to winter sports enthusiasts. These properties often feature essential amenities such as fireplaces, full kitchens, and ample living space, making them ideal for families or groups enjoying a ski getaway.Additionally, rentals in the surrounding areas, including Buckland and Hawley, provide further choices, often featuring larger homes with scenic views of the nearby mountains. Many of these properties come equipped with hot tubs or large decks, superb for unwinding after a day on the slopes. The proximity to local dining options and shops enhances the convenience of your stay.For those who enjoy outdoor activities beyond skiing, the nearby Mohawk Trail offers excellent hiking and scenic views, with some rentals conveniently located near these trails.
What is the most popular type of holiday rental accomodation in Charlemont?
In Charlemont, holiday houses are the most popular type of holiday rental, with around 36 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, making them ideal for families or groups looking to enjoy the natural beauty of the surrounding region. Additionally, there are about 12 charming cottages, which offer a cozier, more rustic experience, often equipped with essential amenities for a comfortable stay. Several cabins, apartments, and condos are also available, providing varied options to suit different preferences and group sizes.
Are there any family house rentals in Charlemont?
In Charlemont, Massachusetts, there are numerous family-friendly holiday rentals available, with around 16 options to choose from. This charming town is situated near the scenic Mohawk Trail, offering a range of outdoor activities for visitors of all ages. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and amenities such as game rooms or outdoor patios, superb for relaxed gatherings after a day of adventure.Families can explore nearby attractions like the Berkshire East Mountain Resort, which provides opportunities for skiing, mountain biking, and zip-lining. Additionally, the area is rich in natural beauty, with plenty of hiking trails and picturesque spots along the Deerfield River.
Are there pet-friendly house rentals in Charlemont?
In Charlemont, Massachusetts, there are several pet-friendly house rentals available, offering a range of amenities for travellers. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces such as decks or patios where pets can enjoy the fresh air. Additionally, some rentals may include conveniences like laundry facilities and Wi-Fi, suiting families and groups looking for a comfortable stay.The surrounding area is rich in natural beauty, with opportunities for outdoor activities that are pet-friendly. Nearby attractions include the picturesque Mohawk Trail, which is superb for hiking and exploring with your furry companions.
Are there any remote work holiday rentals in Charlemont?
In Charlemont, Massachusetts, there are around 60 holiday rentals ideal for remote work. This picturesque area, located in the Berkshire Mountains, offers a tranquil environment superb for balancing work and leisure. Many properties cater to remote workers, featuring dedicated workspaces with desks and comfortable chairs, as well as high-speed Wi-Fi to ensure productivity.The rentals often include amenities such as fully equipped kitchens, allowing for convenient meal preparation, and cozy living areas to unwind after a day of work. Some accommodations may even have access to outdoor spaces, superb for taking breaks while enjoying the stunning natural surroundings.Charlemont is also known for its proximity to outdoor activities, including hiking, river rafting, and skiing in the winter months, making it a great choice for those looking to combine work with adventure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Charlemont?
In Charlemont, popular rental amenities include fully equipped kitchens, allowing guests to prepare meals during their stay. Many properties also feature inviting fireplaces, superb for warming up after a day exploring the outdoors. Additionally, rentals often come with decks or patios, providing lovely spaces to relax and enjoy the surrounding scenery. Onsite parking is commonly available, making access convenient for those travelling by car.
When is the best time to visit Charlemont for a holiday rental?
The best time to visit Charlemont for a holiday rental is during the peak season from June to August, with July being particularly popular. This vibrant period attracts many outdoor enthusiasts eager to explore the stunning landscapes and partake in activities such as white-water rafting on the Deerfield River or hiking along the scenic trails of the surrounding mountains.During the summer months, you can expect warm temperatures ranging from 15 to 30 degrees Celsius, making it ideal for outdoor fun and exploration. The lush greenery and lively option create a superb backdrop for family gatherings or adventurous getaways, ensuring that visitors can enjoy the natural beauty and recreational opportunities that Charlemont has to offer.For those looking to save on accommodation costs, consider visiting in November. This month is quieter and presents a unique charm, with the crisp air and beautiful autumn foliage providing a picturesque setting for peaceful hikes and leisurely drives. You'll have the chance to experience the tranquillity of Charlemont while still enjoying its captivating natural scenery.Ultimately, your choice will depend on whether you prefer the excitement of summer activities or the serene beauty of the autumn landscape.
What are the top attractions in Charlemont?
In Charlemont, visitors can engage in the beauty of the western Massachusetts landscape, particularly in the picturesque Berkshire Mountains. One of the main attractions is the Mohawk Trail, a scenic byway that offers breathtaking views of the surrounding nature, especially during the autumn foliage season. The nearby Berkshire East Mountain Resort provides opportunities for outdoor activities such as skiing, mountain biking, and zip-lining, making it a popular destination for adventure seekers.For those interested in history and culture, the Charlemont Historical Society offers insights into the town's rich heritage. The area is also known for its rafting experiences on the Deerfield River, which attract thrill-seekers and nature lovers alike. Additionally, the nearby Zoar Outdoor Adventure Resort offers guided rafting trips and other outdoor activities, ensuring that visitors have plenty of options for exploration and adventure.
Are all fees included in the Charlemont 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 Charlemont holiday homes with parking?
Stayz offers a wide selection of holiday homes in Charlemont 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 Charlemont holiday homes?
You can find great discounts on holiday homes in Charlemont 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 Charlemont holiday home booking on Stayz?
To find Charlemont 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 Charlemont?
A long-stay holiday home in Charlemont 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 Charlemont holiday home?
Book your Charlemont 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 Charlemont?
Prices for holiday homes in Charlemont 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 Charlemont 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.

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