Best apartment offers in The Berkshires, MA

1721 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
The Berkshires, MA apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow - The Berkshires, MA
10 125 reviews
The Berkshires, MA
22/09 – 25/09
A$1029/nighttotal: A$3087 (3 )

Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow

4 2
apartment , Monterey
This family-friendly holiday home is situated near Monterey, within a 3km radius of Beartown State Forest and Bidwell House Museum, and within 10km of Ashintully Gardens and McLennan Reservation. The property has received excellent ratings for its cleanliness, location and user experience.
The accommodation has four bedrooms and a floor area of 288 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a fireplace, a patio with a barbecue grill, a fitness centre, and a garden.
Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington - The Berkshires, MA
10 11 reviews
The Berkshires, MA
22/09 – 25/09
A$1994/nighttotal: A$5982 (3 )

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

5 2
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.
The Pinnacle House At Otis Ridge Ski Area! - The Berkshires, MA
9.8 174 reviews
The Berkshires, MA
23/10 – 25/10
A$487/nighttotal: A$974 (2 )

The Pinnacle House At Otis Ridge Ski Area!

1 2
apartment , Otis
This four-bedroom apartment is located just a short distance from popular Berkshire destinations like Jacob's Pillow, Tanglewood, and the Norman Rockwell Museum, offering a peaceful escape in the tranquil surroundings of Otis Ridge Ski Area. It has consistently received excellent ratings for cleanliness, location, and overall user experience.
The spacious apartment comfortably accommodates up to eight guests and features a well-equipped kitchen, a private garden, and parking. Guests can enjoy outdoor meals on the patio with a gas grill, relax in the living area, or explore the nearby hiking trails, swimming spots, and local restaurants.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.6 132 reviews
The Berkshires, MA
14/08 – 17/08
A$979/nighttotal: A$2937 (3 )

Treetop Hideaway In Tyringham

4 2
apartment , Tyringham
This secluded log cabin is located in Monterey, just outside of Tyringham, bordering conservation land and offering stunning views of the Tyringham Valley, just a short drive from the village. Guests have consistently rated the accommodation excellent for location, cleanliness, and overall experience.
The spacious cabin, with four bedrooms and two bathrooms, comfortably accommodates up to eight guests. Enjoy the fresh air on the wraparound deck, relax in the hot tub on the screened porch, and explore the surrounding conservation land for hiking and wildlife viewing.

Best The Berkshires, MA holiday apartments with air conditioning

Real Estate:therapy - Lake, Laundry, Love It - The Berkshires, MA
9.8 362 reviews
The Berkshires, MA
23/10 – 25/10
A$407/nighttotal: A$814 (2 )

Real Estate:therapy - Lake, Laundry, Love It

1 2
apartment , Becket
This apartment is located in the Sherwood Forest Community, just 18 minutes from the centre of Lee, Massachusetts, offering a peaceful retreat in a woodland setting. It has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The self-catering property has three bedrooms, accommodating up to six guests, and features a spacious open-plan living area, kitchen, and dining room. The apartment comes equipped with a range of amenities, including a fully equipped kitchen, a washing machine and dryer, comfortable beds, and high-speed internet access. Guests can also enjoy access to a private lake with a canoe and paddleboard, a barbecue area, and a level 2 EV charger.
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.
Konkapot River Retreat - The Berkshires, MA
The Berkshires, MA
14/08 – 17/08
A$650/nighttotal: A$1950 (3 )

Konkapot River Retreat

1 2
apartment , New Marlborough
This two-bedroom, two-bathroom flat offers direct access to the Konkapot River and secluded hiking trails at the adjacent Great Barrington National Fish Hatchery, located in the scenic Berkshires region of New Marlborough.
This self-catering accommodation for four guests features a kitchen and air conditioning, providing an ideal base for enjoying the natural beauty and outdoor pursuits available year-round.
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-swimming, Canoeing - The Berkshires, MA
9.8 15 reviews
The Berkshires, MA
23/10 – 25/10
A$505/nighttotal: A$1010 (2 )

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-swimming, Canoeing

2 2
apartment , Becket
This Becket Sherwood Forest holiday home is situated 4km from Pyramid Lake and within 10km of both Jacob's Pillow Dance Festival and the Iroquois Waterfront.
The two-bedroom property sleeps seven, boasts a jacuzzi, terrace, garden, free Wi-Fi, BBQ facilities and parking, and is perfect for families, with pets welcome.

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

Beautiful Berkshire Family Home - The Berkshires, MA
9.4 3 reviews
The Berkshires, MA
22/09 – 25/09
A$928/nighttotal: A$2784 (3 )

Beautiful Berkshire Family Home

5 2
apartment , Monterey
This private Berkshire post and beam house is located in a secluded woodland setting, offering privacy yet situated only 5 kilometres from Monterey village amenities, 19 kilometres from Butternut Family Skiing and Lake Garfield, and 16 kilometres from the Appalachian Trail.
This spacious 232 square metre dwelling, ideal for up to 12 guests across its 5 bedrooms and 3 bathrooms, boasts a well-equipped kitchen, throughout-house Wi-Fi, a wood-burning stove, and is pet-friendly, with outdoor recreation including swings and hammocks available.
Lakefront Otis Home W/ Stunning Views & Boats! - The Berkshires, MA
10 13 reviews
The Berkshires, MA
22/09 – 25/09
A$987/nighttotal: A$2961 (3 )

Lakefront Otis Home W/ Stunning Views & Boats!

2 2
apartment , Otis
This waterfront property is located in Otis, just 3 km from Ashintully Gardens and 4 km from Otis State Forest and Otis Ridge Ski Resort, offering a peaceful retreat in the heart of the Berkshires. The apartment has consistently received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
This spacious 212 square metre property comfortably accommodates up to 6 guests and features two bedrooms and three bathrooms. It offers a well-stocked kitchen, luxurious bathrooms, high-speed internet, two Smart TVs, a wireless sound system, a telescope, three spacious decks, a screened-in deck with an outdoor dining area, a gas grill, a seasonal hot tub, and access to a rowboat, kayak, and a community boat dock across the street.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 13 reviews
The Berkshires, MA
31/08 – 03/09
A$2019/nighttotal: A$6057 (3 )

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

4 2
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.
Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 16 reviews
The Berkshires, MA
26/08 – 02/09
A$864/nighttotal: A$6048 (7 )

Berkshires Oasis Retreat: Art Meets Nature

1 1
apartment , Otis
This Otis property, a three-bedroom house sleeping eight, is situated on an eight-acre wooded plot near Berkshire attractions.
The spacious, modern house features a well-equipped kitchen, private pool (seasonal), a finished basement with laundry facilities, and strong WiFi; the main floor is accessible for guests with limited mobility.

Best The Berkshires, MA apartment rentals with a garden

Sailor & Queen: Artist-inspired Berkshire Home - The Berkshires, MA
10 1 review
The Berkshires, MA
14/08 – 17/08
A$463/nighttotal: A$1389 (3 )

Sailor & Queen: Artist-inspired Berkshire Home

1 2
apartment , Otis
This garden-level suite in Otis is located in the Berkshires, offering a secluded natural setting with artist-crafted touches.
This 2-bedroom, 1-bathroom flat accommodates up to 4 guests, featuring a kitchen, garden, and parking, ideal for a peaceful retreat in the Berkshires.
Berkshires Hideaway! Summer Serenity - The Berkshires, MA
9.9 159 reviews
The Berkshires, MA
23/10 – 25/10
A$614/nighttotal: A$1228 (2 )

Berkshires Hideaway! Summer Serenity

1 2
apartment , Otis
This spacious apartment is located in Otis, Massachusetts, just a short distance from Otis Reservoir and an Audubon preserve, offering a peaceful retreat in the heart of the Berkshires. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to ten guests. The property features a well-equipped kitchen, a wraparound deck, a private backyard, and a fireplace, making it perfect for families and groups seeking a relaxing getaway.
Waterfront Oasis In Heart Of Berkshires - The Berkshires, MA
10 20 reviews
The Berkshires, MA
22/09 – 25/09
A$1256/nighttotal: A$3768 (3 )

Waterfront Oasis In Heart Of Berkshires

3 2
apartment , Sandisfield
This Sandisfield waterfront property, a 223 square metre (2400 sq ft) house, is situated within 14.5 kilometres of Beartown State Forest, Bidwell House Museum, and Questing, with Ashintully Gardens and Dry Hill also nearby.
The three-bedroom dwelling sleeps six, boasting a fully equipped kitchen, Jacuzzi, terrace, garden, parking, free Wi-Fi, and a DVD player; water activities are possible due to the waterfront location.
Ridge House At Otis Ridge Ski Area - The Berkshires, MA
10 52 reviews
The Berkshires, MA
31/08 – 03/09
A$420/nighttotal: A$1260 (3 )

Ridge House At Otis Ridge Ski Area

1 2
apartment , Otis
The Ridge House is situated right next to the Otis Ridge Ski Area, making it perfect for those seeking a winter sports getaway. The property has consistently received excellent ratings for its cleanliness, location and overall user experience.
The apartment is spacious and can comfortably accommodate up to six guests. The well-equipped kitchen, outdoor deck with grill, and access to games and Wi-Fi provide everything you need for a relaxing and enjoyable stay.
©2026 cozycozy.com