Vacation 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

Quality Family-Friendly Holiday Rentals in The Berkshires, MA

Base your high-altitude family hikes out of a spacious, rugged property with plenty of room for the kids at mountain rentals in The Berkshires, MA.

Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home. - The Berkshires, MA
9.9 350 reviews

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

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.
Mountain Refuge - The Berkshires, MA
9.3 21 reviews

Mountain Refuge

apartment, Otis
This charming cottage is located just a 10-minute drive from Ski Butternut, a popular ski resort, and close to Otis Reservoir, offering scenic views and opportunities for water activities. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cottage offers comfortable accommodation for up to eight guests, with cozy bedrooms and additional sleeping options in the form of sofa beds. Guests can enjoy amenities such as a fully equipped kitchen, a hot tub (available for an additional fee), and a garden, making it ideal for families and groups seeking a relaxing getaway.
East Otis Reservoir Cabin W/ Porch - Walk To Lake! - The Berkshires, MA
9.0 23 reviews

East Otis Reservoir Cabin W/ Porch - Walk To Lake!

cabin, Otis
The East Otis Reservoir Cabin with Porch - Walk to Lake! is located in East Otis, just a short walk from the reservoir and within a 25-mile radius of attractions like Cranwell Spa & Golf Club, Tanglewood, and Norman Rockwell Museum. This charming dwelling has received very good user ratings and excellent scores for location and cleanliness.
The cabin is a comfortable 67 square metres with two bedrooms and one bathroom, sleeping up to four guests. It offers a fully equipped kitchen with a fridge and microwave, air conditioning, a terrace, a garden, parking, and direct access to the reservoir for swimming, fishing, and kayaking.
Berkshires Lakefront Boho Modern Retreat - The Berkshires, MA
10 21 reviews

Berkshires Lakefront Boho Modern Retreat

cabin, Otis
Watson Pond Lodge, a lakefront property in Otis, Massachusetts, offers stunning panoramic lake views and is conveniently located near Otis Ridge Ski Area, approximately a short drive from other Berkshire attractions such as Tanglewood and Jacob's Pillow.
This three-bedroom, two-bathroom lodge sleeps six guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, a fire pit, BBQ facilities, and a private dock (removed in winter).

Holiday Rentals with a Balcony in The Berkshires, MA

Check out mountain holiday rentals with a balcony in The Berkshires, MA for breathtaking elevated views.

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires, MA
9.6 133 reviews

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns

cabin, Sandisfield
This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.8 48 reviews

The Meadows House @ Otis Ridge W/ 7-person Hot Tub

apartment, Otis
This house is located just half a mile from Otis Ridge, offering easy access to hiking trails and scenic views. It is also within a short drive of County Beach, Ashintully Gardens, Otis Reservoir, and Jacob's Pillow, making it a great base for exploring the area. The property has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The house has three bedrooms, three bathrooms, and can accommodate up to seven guests, with a total floor area of 153 square metres. It features a fully equipped kitchen, a fireplace, a spa tub, a garden, barbecue grills, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Becket Home W/ 3-season Porch: Walk To Lake Access - The Berkshires, MA
9.6 11 reviews

Becket Home W/ 3-season Porch: Walk To Lake Access

apartment, Becket
This two-bedroom apartment is situated in the Sherwood Forest district of Becket, just 0.6 kilometres from the Sherwood Shoppe and within an 8-kilometre radius of Jacob's Pillow.
The 76 square metre property boasts a private backyard with a fire pit, a screened porch, and access to canoes, paddleboards, and life vests for exploring the lake, accommodating up to 7 guests.
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.

Frequently asked questions about holiday rentals in The Berkshires, MA

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

    For a first-timer, you'll want to visit the iconic Tanglewood Music Center for a concert under the stars, explore the stunning natural beauty of Mount Greylock, the highest peak in Massachusetts, and experience the vibrant art scene at the Clark Art Institute.
  • 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 charming village with a lovely main street and is a great base for exploring the Berkshires. It's close to many attractions and has a good selection of vacation rentals.
  • What are the most popular Airbnbs in The Berkshires, MA?

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

    The Berkshire Museum is great for kids, with interactive exhibits and a dinosaur hall. For outdoor fun, the Hancock Shaker Village offers a glimpse into a unique way of life and the Berkshire Botanical Garden has beautiful trails and a children's garden.
  • 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?

    Peak season in the Berkshires is from June to October, especially during foliage season in autumn. Booking your vacation rental well in advance is recommended, particularly if you're travelling during these popular months.
  • 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 runs from late June to August and features world-class classical music performances. The Jacob's Pillow Dance Festival in Becket showcases contemporary and traditional dance styles.
  • What are the best rentals or Airbnbs with a jacuzzi in The Berkshires, MA?

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

    Hiking the Appalachian Trail, exploring the free-admission Berkshire Museum, or taking a scenic drive along the Mohawk Trail are great budget-friendly options. You can also enjoy a picnic at the beautiful Hopkins Memorial Forest.
  • What are the best restaurants with local dishes in Monts Berkshire?

    The Red Lion Inn in Stockbridge is a classic spot with a New England menu, while the Wheatleigh in Lenox serves up elegant farm-to-table dishes. For something more casual, try the Berkshire Mountain Distillery for their locally crafted spirits and small plates.
  • What are the best walking or cycling routes in Monts Berkshire?

    The scenic 18.5 km (11.5 miles) Ashuwillticook Rail Trail is a popular choice for walkers and cyclists, offering beautiful views of the Berkshire countryside. You can also explore the 16 km (10 miles) Taconic Crest Trail for stunning mountain views.
  • Are there pet-friendly attractions in Monts Berkshire?

    Yes, many places in the Berkshires are dog-friendly. The Mount, Edith Wharton's former estate, welcomes well-behaved dogs on leash. The Hopkins Memorial Forest has trails suitable for dogs, and many restaurants have outdoor seating where you can enjoy a meal with your furry friend.
  • What are the benefits of choosing a vacation rental in Monts Berkshire?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for larger groups or families.
  • What are the top sports attractions and facilities in Monts Berkshire?

    The Berkshires are home to several ski resorts, such as Butternut, Jiminy Peak, and Catamount, offering downhill skiing, snowboarding, and cross-country skiing in the winter. For other sports, you can find golf courses, tennis courts, and hiking trails throughout the region.

Popular destinations

Holiday Rentals with a Sauna in The Berkshires, MA

Soothe your hiking muscles and sweat out the trail dust at mountain holiday rentals with a sauna in The Berkshires, MA.

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.
Heated Pool, Hot Tub, Game Room, Sauna! - The Berkshires, MA
9.9 36 reviews

Heated Pool, Hot Tub, Game Room, Sauna!

apartment, New Marlborough
Casa Mia is a spacious holiday home located in New Marlborough, just 10 kilometres from Great Barrington and 5 kilometres from Ski Butternut, offering a peaceful retreat in the quiet countryside. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This five-bedroom property, with a capacity for 12 guests, is designed with an open layout, providing ample space for families and groups. Guests can enjoy a range of amenities, including a swimming pool, hot tub, sauna, and a fully equipped kitchen, as well as entertainment options like a games room and a bocce court.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires, MA
10 22 reviews

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This Monterey lodge is located among tall pines, a short distance from Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This three-bedroom, three-bathroom holiday home accommodates eight guests and features a fully equipped kitchen, a wood-fired sauna, a garden, and parking, with a rustic log cabin feel and an outdoor wood-fired sauna for relaxation.
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.

Holiday Rentals with a Fireplace in The Berkshires, MA

Share a bottle of wine by a crackling stone hearth after an outdoor trek at mountain holiday rentals with a fireplace in The Berkshires, MA.

Berkshires Cabin 2 Mi To Appalachian Trail! - The Berkshires, MA
9.7 46 reviews

Berkshires Cabin 2 Mi To Appalachian Trail!

cabin, Otis
The Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, just 3.2km from the Appalachian Trail and within a short drive of attractions such as Cranwell Spa & Golf Club, Tanglewood, and Tanglewood Musical Center. The property has excellent user, location, and cleanliness ratings.
This 3-bedroom holiday home is 111 square metres and can accommodate up to 7 guests. The cabin has a fully equipped kitchen, a garden, a spa, free Wi-Fi, a flat-screen TV, and parking.
Berkshire Lake At The Pillow, And Ev! - The Berkshires, MA
9.6 18 reviews

Berkshire Lake At The Pillow, And Ev!

apartment, Becket
This waterfront property in Lee, Massachusetts is just a short drive from Jacob's Pillow, October Mountain State Forest, and Pyramid Lake, offering easy access to both outdoor activities and cultural attractions. The house has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The spacious three-bedroom home can comfortably accommodate up to six guests and features a fully equipped kitchen, a fireplace, and a private garden with barbecue facilities. Guests can enjoy modern amenities like free Wi-Fi, a washing machine, a dishwasher, and a Smart TV, as well as the convenience of two bathrooms.
Cabin With Spectacular Views Of Robin Hood Lake - The Berkshires, MA
9.5 121 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.
Light-filled Cottage - The Berkshires, MA
10 4 reviews

Light-filled Cottage

apartment, New Marlborough
This four-bedroom New Marlborough cottage, perfect for families, is situated in a secluded woodland setting near numerous lakes and waterfalls, offering easy access to local cafes and restaurants.
The self-catering property sleeps five, features a wood-burning stove, high-speed internet, a garden, and a fitness centre, and provides DVDs, books, and a sound system for guest entertainment.

Best The Berkshires, MA holiday rentals with parking

Berkshires Cabin In Woods With Mountain Views - The Berkshires, MA
10 136 reviews

Berkshires Cabin In Woods With Mountain Views

cabin, Sandisfield
Overflow Cabin Retreat On Otis Reservoir - The Berkshires, MA
10 6 reviews

Overflow Cabin Retreat On Otis Reservoir

cabin, Otis
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.7 212 reviews

The Meadows House @ Otis Ridge W/ 7-person Hot Tub

apartment, Otis
Screened Porch W/ Lake View! Tolland Family Haven - The Berkshires, MA
No reviews

Screened Porch W/ Lake View! Tolland Family Haven

apartment, Tolland
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