Best apartment offers in The Berkshires, MA

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The Berkshires, MA apartments
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1721 Holiday apartments in The Berkshires, MA

Best family friendly The Berkshires, MA Holiday Apartments

Among the 1721 accommodations in The Berkshires, MA, here are the 4 best family friendly holiday apartments

Converted Berkshire Schoolhouse On A Quiet River - The Berkshires, MA
9.9 168 reviews
The Berkshires, MA
31/08 – 03/09
A$439/nighttotal: A$1317 (3 )

Converted Berkshire Schoolhouse On A Quiet River

1 2
apartment , New Marlborough
This charming cottage is located in the Berkshires, just a short distance from the Butternut ski resort and the town of Great Barrington, offering easy access to both outdoor adventures and cultural attractions. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage features three bedrooms, comfortably accommodating up to five guests. Enjoy a fully equipped kitchen, a spacious garden, a private terrace, and a host of amenities including a BBQ, a coffee grinder, a DVD collection, and a unique "sign the walls" tradition in the bathroom.
The Golden Getaway - The Berkshires, MA
10 1 review
The Berkshires, MA
31/08 – 03/09
A$447/nighttotal: A$1341 (3 )

The Golden Getaway

1 2
apartment , Otis
This lakefront flat in Otis, Massachusetts, offers direct access to the Otis Reservoir within the scenic Berkshires mountains, boasting stunning lake views and a private dock for watercraft.
This family-friendly dwelling sleeps six, featuring two bedrooms and convertible twin beds, a fully equipped kitchen with fridge, freezer and microwave, a garden with a fire pit and covered deck, plus provided kayaks and WiFi, all within a 5-6 vehicle capacity driveway.
Lakes & Leisure: Spacious Berkshire Getaway - The Berkshires, MA
10 6 reviews
The Berkshires, MA
08/07 – 12/07
A$746/nighttotal: A$2984 (4 )

Lakes & Leisure: Spacious Berkshire Getaway

4 4
apartment , Becket
This spacious Berkshire apartment in Becket offers easy access to nearby lakes perfect for kayaking and swimming.
Sleeping up to 12 guests, this four-bedroom, two-bathroom property boasts a well-equipped kitchen, multiple smart TVs, a garden, parking for three cars, and pet-friendly accommodation (maximum two dogs, £40 fee).
Berkshires Modern Cabin With Babbling Brook - The Berkshires, MA
10 14 reviews
The Berkshires, MA
08/07 – 12/07
A$813/nighttotal: A$3252 (4 )

Berkshires Modern Cabin With Babbling Brook

3 4
apartment , Sandisfield
The Cabin is located in the Berkshires, a short walk from a community lake and amenities, and a short drive (around 10km) to popular ski resorts like Otis Ridge and Ski Butternut. It has received excellent ratings for location, cleanliness and overall user experience.
The accommodation has a spacious and open floor plan, ideal for families, and can comfortably sleep up to 7 guests. It offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a wood-burning stove, and a dedicated kids' play area, as well as easy access to hiking trails, cultural attractions, and winter sports.

Best The Berkshires, MA holiday apartments with air conditioning

Lake House With Private Beach! - The Berkshires, MA
The Berkshires, MA
14/08 – 16/08
A$620/nighttotal: A$1240 (2 )

Lake House With Private Beach!

2 2
apartment , Becket
This lakeside flat in the Berkshires offers direct access to a sandy beach and dock, situated 16 kilometres from Jacob's Pillow and 48 kilometres from Tanglewood.
This two-bedroom property accommodates up to seven guests, featuring a well-equipped kitchen, air conditioning, internet, a sunroom with lake views, a canoe/kayak, and an outdoor fire pit.
Rustic Berkshire Getaway - The Berkshires, MA
9.4 223 reviews
The Berkshires, MA
14/08 – 16/08
A$528/nighttotal: A$1056 (2 )

Rustic Berkshire Getaway

2 2
apartment , Becket
This two-bedroom flat is located in Otis, just a few kilometers from Jacobs Pillow and a range of outdoor activities including lakes, hiking trails, and skiing areas. It has been consistently rated excellent for its cleanliness, location, and overall experience.
The apartment, perfect for a family or group of friends, boasts a rustic-inspired design with a top-floor location offering privacy and views. You can enjoy a fully equipped kitchen with a fridge and dishwasher, air conditioning, a garden, parking, and a digital guidebook with local information.
Sunset Falls: A Berkshire Mountain Luxury Retreat - The Berkshires, MA
10 3 reviews
The Berkshires, MA
08/07 – 12/07
A$9474/nighttotal: A$37896 (4 )

Sunset Falls: A Berkshire Mountain Luxury Retreat

1 4
apartment , New Marlborough
This luxurious apartment is located in the picturesque Berkshires of western Massachusetts, 32 kilometres from Great Barrington, a town known for its cultural experiences, restaurants, and shops. The apartment offers a range of amenities including a hot tub, steam room, radiant heated floors, three fireplaces, a fully equipped chef's kitchen, a gym, a 2-car heated garage, a children's nook with books and games, a dedicated kids room with 6 queen over queen bunk beds, accommodating up to 12 guests, and a great room with a pool table, foosball, darts, arcade games, an 85” TV, and a wet bar with a wine fridge and a kegerator.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 13 reviews
The Berkshires, MA
18/08 – 25/08
A$2249/nighttotal: A$15743 (7 )

Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay

4 7
apartment , Monterey
This four-bedroom apartment is located in the Berkshires, a mountainous region of western Massachusetts, just a short drive from the Berkshire Botanical Gardens and the Norman Rockwell Museum. The apartment has received excellent ratings from previous guests and is ideal for families or groups looking for a comfortable and stylish retreat.
The apartment is spread over three floors and can comfortably accommodate up to 12 guests. It features a spacious open plan living area, a modern kitchen, four bathrooms, a sauna, a hot tub, a tennis court, a garden, and a terrace with stunning lake views.

Frequently asked questions about apartment rentals in The Berkshires, MA

  • What are the must-see attractions for a 2 days stay in Monts Berkshire?

    For a two-day trip, you'll want to visit the Clark Art Institute in Williamstown, which has a beautiful collection of Impressionist and Post-Impressionist art. You can also explore the Berkshire Museum in Pittsfield, which features a diverse range of exhibits. For a taste of nature, head to Mount Greylock State Reservation, the highest point in Massachusetts, offering stunning views.
  • What are the best apartments in The Berkshires, MA?

    Among the apartments in The Berkshires, MA, Peace And Quiet On The Lake, Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home and Artist Cottage are the most popular ones.

  • Which neighborhoods in Monts Berkshire are best for renting an apartment?

    If you're looking for a vibrant atmosphere, consider renting in downtown Great Barrington or Lenox. These towns offer a good mix of restaurants, shops, and cultural attractions. If you prefer a quieter setting, Stockbridge or Williamstown are great choices, with charming villages and picturesque surroundings.
  • What are the best apartments with a pool in The Berkshires, MA?

  • What are the top cultural and historical sites in Monts Berkshire?

    The Berkshires are rich in history and culture. You can visit the Tanglewood Music Center in Lenox, renowned for its summer music festival. For a glimpse into the past, explore the Hancock Shaker Village in Hancock, which showcases the unique lifestyle of the Shakers. The Norman Rockwell Museum in Stockbridge is another must-see, showcasing the iconic American artist's works.
  • What are the best apartments with a jacuzzi in The Berkshires, MA?

  • What makes Monts Berkshire unique or famous?

    The Berkshires are known for their stunning natural beauty, with rolling hills, forests, and lakes. They are also a cultural hub, home to renowned art museums, music festivals, and theatre productions. The region is also famous for its charming towns and villages, offering a peaceful escape from the hustle and bustle of city life.
  • What are the best apartments for families and kids in The Berkshires, MA?

  • Where can you find the best local markets and street food in Monts Berkshire?

    The Berkshires have several farmers' markets throughout the year, offering fresh produce, local crafts, and delicious treats. The Great Barrington Farmers Market is a great option, held every Saturday from June to October. You can also find street food vendors at events like the Tanglewood Music Festival and the Berkshire County Fair.
  • What are the best pet friendly apartments in The Berkshires, MA?

    The best pet friendly apartments in The Berkshires, MA are Peace And Quiet On The Lake, Victorian Manor 5 Bathrooms and Sunny Berkshire Studio Apartment.

  • How is the public transportation system in Monts Berkshire?

    Public transportation in the Berkshires is limited, especially compared to larger cities. The Berkshire Regional Transit Authority (BRTA) operates buses connecting various towns, but frequency and routes can be limited. It's recommended to have a car for exploring the region.
  • What are the best apartments with parking in The Berkshires, MA?

  • Which seasonal events or festivals should apartment renters look forward to in Monts Berkshire?

    The Berkshires come alive with festivals throughout the year. In the summer, the Tanglewood Music Festival is a major highlight, attracting renowned musicians and classical music enthusiasts. Autumn brings vibrant foliage and the popular Apple Picking season. The winter months offer festive events like the Christmas in Lenox celebration.
  • What amenities are typically included in apartments in Monts Berkshire?

    Apartments in the Berkshires typically include basic amenities like central heating, hot water, and kitchen appliances. Some apartments may offer additional features like laundry facilities, parking, or a private balcony. Availability and specific amenities vary depending on the apartment and its location.
  • What leisure activities are available for relaxation in Monts Berkshire?

    The Berkshires offer a wide range of leisure activities for relaxation. You can enjoy hiking trails in the Appalachian Mountains, go kayaking or canoeing on local lakes, or simply relax at a spa or hot springs. The region also has numerous golf courses and scenic biking paths.

Destinations nearby

Best The Berkshires, MA holiday apartments with parking

Lakefront Bungalow - The Berkshires, MA
9.8 11 reviews
The Berkshires, MA
08/07 – 12/07
A$1094/nighttotal: A$4376 (4 )

Lakefront Bungalow

3 4
apartment , Otis
This pet-friendly bungalow is located in Otis, Massachusetts, just 7km from Tolland State Forest and close to Otis Reservoir. It has received excellent user ratings and is a popular choice for travellers visiting the area.
The bungalow has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 7 guests. It is fully equipped with modern amenities, including air conditioning, Wi-Fi, a fully equipped kitchen, a washer and dryer, and a spacious garden with a fire pit.
Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington - The Berkshires, MA
10 11 reviews
The Berkshires, MA
08/07 – 12/07
A$1951/nighttotal: A$7804 (4 )

Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington

5 4
apartment , Monterey
This Monterey holiday home is situated approximately 2.7 kilometres from the Bidwell House Museum and within a 9.6-kilometre radius of several attractions including McLennan Reservation, Ashintully Gardens, Dry Hill, and Lake Buel.
This spacious five-bedroom property, boasting 228 square metres of floor area, comfortably accommodates up to 14 guests and features a fitness centre, Jacuzzi, and a full kitchen with modern appliances.
Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home. - The Berkshires, MA
9.9 340 reviews
The Berkshires, MA
13/11 – 16/11
A$1158/nighttotal: A$3474 (3 )

Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home.

4 5
apartment , Monterey
This beautiful home is located in the Berkshires, a scenic region of Massachusetts, just 20 minutes from Great Barrington and 2.5 hours from both New York City and Boston. It has received excellent ratings for location, cleanliness, and overall user experience.
The property spans 214 square metres and comfortably accommodates up to 9 guests in its 4 bedrooms and 2 bathrooms. It offers a range of amenities, including a fully equipped kitchen, a hot tub, a fire pit, and a screened sunroom with stunning lake views.
Bosworth Tap Room - The Berkshires, MA
9.9 99 reviews
The Berkshires, MA
13/11 – 16/11
A$666/nighttotal: A$1998 (3 )

Bosworth Tap Room

1 5
apartment , Sandisfield
This historic house is located in the southeast corner of the Berkshires, around 48 kilometres from the nearest shopping centre, offering a peaceful retreat in the beautiful countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has four bedrooms and one bathroom, comfortably accommodating up to six guests. The house features a fully equipped kitchen, a garden, and air conditioning, alongside modern amenities while retaining its authentic colonial charm.

Best The Berkshires, MA apartment rentals with a garden

Waterfront Oasis In Heart Of Berkshires - The Berkshires, MA
10 48 reviews
The Berkshires, MA
20/11 – 23/11
A$975/nighttotal: A$2925 (3 )

Waterfront Oasis In Heart Of Berkshires

4 5
apartment , Sandisfield
This waterfront property is situated in Sandisfield, just a short distance from Butternut ski resort and tubing, as well as the shops and restaurants of Great Barrington and Lenox. The apartment has received excellent ratings for location, cleanliness, and user experience.
The spacious apartment comfortably sleeps up to seven guests in its four bedrooms and three bathrooms. Guests can enjoy a fully equipped kitchen, a wood-burning stove, a private garden, and stunning views of the water.
Cozy Cottage-sunset On The Lake! - The Berkshires, MA
9.6 62 reviews
The Berkshires, MA
14/08 – 16/08
A$891/nighttotal: A$1782 (2 )

Cozy Cottage-sunset On The Lake!

3 2
apartment , Otis
This Berkshire holiday home is situated in a private lake community near Otis and Becket, Massachusetts, approximately 16km from both towns and the Otis Reservoir marina, offering easy access to the Appalachian Trail and the Knox Trail.
The three-bedroom, two-bathroom property sleeps six guests, features a deck with a fire pit overlooking the lake, provides fast fibre-optic internet, and includes kayaking and fishing opportunities on the lake, plus scenic walks to Watson Pond and Lily Pond.
Stone Tudor In Monterey Village - The Berkshires, MA
9.4 93 reviews
The Berkshires, MA
20/11 – 23/11
A$533/nighttotal: A$1599 (3 )

Stone Tudor In Monterey Village

3 5
apartment , Monterey
This Tudor-style house is situated in Monterey Village, just a short walk from the village centre and a 10-minute drive from Great Barrington, offering easy access to local amenities and attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house features three bedrooms and three bathrooms, comfortably accommodating up to seven guests. It offers a unique blend of Tudor charm and industrial elements, with a glass and stone tower, a spiral staircase, and a metal bridge connecting the main house to the kitchen. Guests can enjoy multiple fireplaces, a spacious garden, and a variety of entertainment options, including board games, video consoles, and streaming services.
Lakeside Berkshires Chalet | Sauna & Fireplace - The Berkshires, MA
The Berkshires, MA
20/11 – 23/11
A$663/nighttotal: A$1989 (3 )

Lakeside Berkshires Chalet | Sauna & Fireplace

3 5
apartment , Becket
This Becket flat is located on the wooded shores of Longbow Lake, offering a private dock and easy access to Jacob's Pillow, just minutes away, and Tanglewood, a 40-kilometre drive.
This 129 square metre property accommodates up to 8 guests across 3 bedrooms and a den, featuring a wood-burning fireplace, a private sauna, a spacious deck, and proximity to Ski Butternut (under 48 kilometres) and Jiminy Peak Mountain Resort (approximately 72 kilometres).
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