Holiday Rentals in The Berkshires, MA

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The Berkshires, MA holiday rentals
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3329 Holiday rentals and Airbnb in The Berkshires, MA

Best family friendly The Berkshires, MA holiday rentals

Among the 3329 accommodations in The Berkshires, MA, here are the 4 best family friendly rentals

Modern Escape In The Woods Of The Berkshires - 4br - The Berkshires, MA
9.7 49 reviews

Modern Escape In The Woods Of The Berkshires - 4br

apartment, Monterey
This four-bedroom apartment is located in the Berkshires, a scenic region of western Massachusetts, a 320km drive from Monterey and just 10 minutes from Ski Butternut. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has three bathrooms and can accommodate up to eight guests. It offers a modern kitchen, a private pool, a garden, a fitness centre, and a range of outdoor activities, including hiking and horseback riding.
Lake Front Retreat - Stylish Berkshire  Home - The Berkshires, MA
9.8 180 reviews

Lake Front Retreat - Stylish Berkshire Home

apartment, Becket
This renovated mid-century home is located on Long Bow Lake, a peaceful lake just 32 kilometres from Downtown Lee, with shops, hiking trails and the Otis Ridge ski area nearby. The property has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
This spacious split-level house sleeps six guests and includes four bedrooms and two bathrooms. The home has a fully equipped kitchen, a garden, a tennis court, a private dock, kayaks, a ping pong table, a Weber gas grill, and a screened-in porch, perfect for enjoying the beautiful scenery and outdoor activities.
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.4 63 reviews

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey
This luxurious four-bedroom lakeside property near Lake Garfield in the Berkshires offers uninterrupted views and is within driving distance of attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort.
Sleeping up to twelve guests, this three-story house boasts a fully equipped kitchen, a second kitchenette, hot tub, sauna, and access to a seasonal dock, alongside various indoor games including ping pong and pool, making it ideal for families or large groups.
Berkshires Chalet Natural Setting Deck & Fire Pit! - The Berkshires, MA
9.8 27 reviews

Berkshires Chalet Natural Setting Deck & Fire Pit!

chalet, Otis
This charming chalet is located in the Berkshires, a short drive from Tanglewood and Jacob's Pillow, and a mile from Otis Ridge ski area, offering a peaceful retreat in a beautiful setting. This property has consistently received excellent ratings for its cleanliness, location and overall experience.
The chalet has four bedrooms, three bathrooms, and can comfortably accommodate up to eight guests. It features a spacious living area with a wood-burning stove, a well-equipped kitchen, a large private yard with a fire pit and a screened-in porch, and a variety of amenities for a comfortable stay.

Best The Berkshires, MA holiday rentals with a balcony

Forest Hollow | Waterfront  Kayaks  Wood Stove - The Berkshires, MA
9.4 11 reviews

Forest Hollow | Waterfront Kayaks Wood Stove

apartment, Monterey
This three-bedroom lakefront property in Monterey, Massachusetts, within the Berkshires, offers direct access to Lake Garfield, with two docks and kayaks, and is approximately 0.8 km from the Bidwell House Museum and the Mahaiwe Performing Arts Centre.
The 185 square metre house features a cosy open-plan living area with a fireplace, a downstairs den/games room, a spacious deck, parking for three cars, and sleeps up to six guests, including children accommodated in trundle beds.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 14 reviews

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

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.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.2 11 reviews

Treetop Hideaway In Tyringham

apartment, Tyringham
This log cabin, nestled in the district of Monterey bordering Tyringham, is located within a short drive of attractions like Greenock Country Club, Otis Ridge, Ashintully Gardens, and Berkshire Scenic Railway Museum. This secluded dwelling, situated on 35+ acres of woodland, offers a peaceful retreat with stunning views of the Tyringham Valley, a spacious living area with vaulted ceilings and a fireplace, a modern kitchen, a screen porch with a hot tub, and a wraparound deck.
Little Longbow Lakefront Chalet - The Berkshires, MA
9.0 1 review

Little Longbow Lakefront Chalet

house, Becket
This lakefront chalet in Becket offers direct access to a private beach and is located 20.9 kilometres from Cranwell Spa & Golf Club and 24.1 kilometres from Tanglewood.
This spacious 2-bedroom holiday home, covering 117 square metres, accommodates up to 9 guests and features a balcony with lake views, a well-equipped kitchen, air conditioning, WiFi, and barbecue facilities, with skiing, fishing, and hiking nearby.

Frequently asked questions about holiday rentals in The Berkshires, MA

  • What should a first-time visitor not miss in Monts Berkshire?

    You can't go wrong with a visit to the Clark Art Institute in Williamstown. It's a beautiful museum with an impressive collection of art. If you're looking for something a bit more hands-on, the Berkshire Museum in Pittsfield is also worth checking out.
  • What are the best Airbnb and holiday rentals in The Berkshires, MA?

  • Which neighborhood in Monts Berkshire should you consider for a vacation rental?

    Stockbridge is a popular choice for vacation rentals, as it's centrally located and has plenty of shops, restaurants, and attractions. If you're looking for something a bit more secluded, consider Lenox or Great Barrington.
  • What are the most popular Airbnbs in The Berkshires, MA?

  • What are the top family-friendly attractions in Monts Berkshire?

    The Berkshire Botanical Garden in Stockbridge is a great place to spend a day with the family. There's also the Children's Museum in the Berkshires in North Adams, which is perfect for kids of all ages.
  • What are the best holiday rentals with a pool in The Berkshires, MA?

  • When is the best time to book a vacation rental in Monts Berkshire?

    The Berkshires are popular in the autumn, so if you're planning on visiting during peak season, it's best to book your vacation rental well in advance. Spring and summer are also great times to visit, but you'll find more availability.
  • What are the best rentals for families and kids in The Berkshires, MA?

  • What events or festivals should visitors check out in and around Monts Berkshire?

    The Tanglewood Music Festival in Lenox is a must-see for classical music lovers. There's also the Jacob's Pillow Dance Festival in Becket, which features performances by some of the world's best dancers.
  • What are the best rentals or Airbnbs with a jacuzzi in The Berkshires, MA?

  • What are the best budget-friendly activities in Monts Berkshire?

    There are plenty of free things to do in the Berkshires, including hiking, biking, and exploring the many scenic towns. You can also visit the Norman Rockwell Museum in Stockbridge for a small admission fee.
  • What are the best restaurants with local dishes in Monts Berkshire?

    The Red Lion Inn in Stockbridge is a classic Berkshire restaurant, serving up traditional New England fare. For a more casual dining experience, try the Wheatberry Bakery in Great Barrington.
  • What are the best walking or cycling routes in Monts Berkshire?

    The Appalachian Trail runs through the Berkshires, offering stunning views. There are also plenty of shorter trails to explore, such as the Taconic Crest Trail and the Ashuwillticook Rail Trail.
  • Are there pet-friendly attractions in Monts Berkshire?

    Many of the parks and trails in the Berkshires are pet-friendly. You can also find dog-friendly restaurants and shops in many towns.
  • What are the benefits of choosing a vacation rental in Monts Berkshire?

    Vacation rentals offer more space and privacy than hotels, and they're often more affordable. You can also find rentals in a variety of locations, from bustling towns to secluded country settings.
  • What are the top sports attractions and facilities in Monts Berkshire?

    The Berkshires are home to a number of golf courses, including the Wyantenuck Country Club in Great Barrington and the Cranwell Resort & Spa in Lenox. There are also ski areas, such as Butternut Basin and Jiminy Peak.

Popular destinations

Best The Berkshires, MA holiday rentals with a sauna

Forget-me-not By Avantstay - The Berkshires, MA
No reviews

Forget-me-not By Avantstay

house, Monterey
Forget-Me-Not by AvantStay, a lakefront property in Monterey, California, is situated 23-35km from attractions including the Cranwell Spa & Golf Club, the Norman Rockwell Museum, Haystack Mountain State Park, and Great Falls.
This one-bedroom house boasts four bathrooms, sleeps sixteen guests, and features a fully equipped kitchen, Jacuzzi, sauna, parking, and a terrace; enjoy lakefront views, water activities, and a fireplace.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires, MA
10 1 review

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This log lodge, situated amongst the tall pines of Monterey, Massachusetts, offers a secluded woodland experience and is located a mere few minutes' drive from Beartown State Forest, Lake Garfield, and the Bidwell House Museum.
This pet-friendly lodge accommodates up to eight guests across three bedrooms, featuring a fully equipped kitchen with a fridge and dishwasher, a garden, parking, and an outdoor wood-fired sauna for relaxation.
Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires, MA
9.8 70 reviews

Forget-me-not By Avantstay | Bold Lakefront Escape

house, Monterey
This apartment is located in the Berkshires, a region in western Massachusetts, just 160 kilometers from Monterey, offering stunning views of Lake Garfield. It has received excellent ratings for its location, cleanliness and overall guest experience.
The property is a spacious home with a modern design, suitable for up to 12 guests. Enjoy a range of amenities, including a hot tub, sauna, a fully equipped kitchen, a large deck with a BBQ grill, a ping pong table, and a pool table for entertainment.
Lakefront Chalet | Dock, Sauna & Fireplace - The Berkshires, MA
9.4 3 reviews

Lakefront Chalet | Dock, Sauna & Fireplace

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).

Best The Berkshires, MA holiday rentals with a fireplace

Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating - The Berkshires, MA
9.6 259 reviews

Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating

cabin, Becket
This charming cabin is located in Sherwood Forest, just outside of Becket, within 10km of Pyramid Lake, Iroquis Waterfront, Jacob's Pillow, October Mountain State Forest, and Becket Land Trust Historic Quarry. It enjoys a peaceful setting, offering a tranquil escape from the hustle and bustle of town. This cabin has been rated excellent by previous guests.
The cabin spans 59 square meters and comfortably sleeps up to four guests in its two bedrooms. It boasts a range of amenities, including a fully equipped kitchen, a garden, a terrace, and a fireplace, allowing guests to enjoy both indoor and outdoor relaxation.
Cabin With Spectacular Views Of Robin Hood Lake - The Berkshires, MA
9.5 123 reviews

Cabin With Spectacular Views Of Robin Hood Lake

cabin, Becket
This charming cottage is situated in the Sherwood Forest area of Becket, Massachusetts, just a short distance from Robin Hood Lake and within easy reach of the Berkshires' attractions. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom cottage can accommodate up to six guests and features a fully equipped kitchen with a dishwasher, a washing machine and dryer, and a fire pit for cosy evenings. Enjoy stunning views of Robin Hood Lake from the back porch, perfect for relaxing, fishing, swimming, boating, kayaking, or ice skating and fishing depending on the season.
Waterfront Oasis In Heart Of Berkshires - The Berkshires, MA
10 21 reviews

Waterfront Oasis In Heart Of Berkshires

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.
Beaver Lodge - The Berkshires, MA
10 83 reviews

Beaver Lodge

apartment, Monterey
This three-bedroom cottage is situated in the Berkshires, just a short distance from Tanglewood, Lake Garfield, and Ski Butternut.
The property boasts a spacious layout, accommodating up to six guests, and offers a range of amenities including a fully equipped kitchen, a wood-burning fireplace, and high-speed internet.