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.

Sunny Oasis In The Woods In Otis - The Berkshires, MA
10 15 reviews

Sunny Oasis In The Woods In Otis

apartment, Otis
This Berkshire County house, less than 1.6km from Route 23, offers easy access to Stockbridge, Great Barrington, and Lenox, placing guests near popular Berkshire attractions such as Tanglewood and Jacob's Pillow.
The three-bedroom, two-bathroom property sleeps six, boasting a contemporary open-plan living area, a first-floor den, and outdoor amenities including two kayaks and a mini frisbee golf course; all within a secluded wooded setting.
Imagine Garden. All Year Round Berkshire Home - The Berkshires, MA
10 1 review

Imagine Garden. All Year Round Berkshire Home

apartment, Sandisfield
This property is located in Sandisfield, just 14-16km from Great Barrington, Lee, and Lenox, offering a peaceful escape from the hustle and bustle of city life while being close to attractions and amenities. It consistently receives excellent ratings for cleanliness, location, and overall experience.
This spacious house has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. It comes equipped with a modern kitchen, air conditioning, a garden, a fitness centre, parking, and internet access, making it perfect for families or groups looking for a comfortable and convenient stay.
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.
The Pinnacle House At Otis Ridge Ski Area! - The Berkshires, MA
9.8 176 reviews

The Pinnacle House At Otis Ridge Ski Area!

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.

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.

Bidwell Landing | Lakefront  Spacious - The Berkshires, MA
9.6 8 reviews

Bidwell Landing | Lakefront Spacious

apartment, Monterey
This four-bedroom, four-bathroom lakefront property in Monterey, Massachusetts offers self-service check-in/out and is conveniently located near the Bidwell House Museum and Mahaiwe Performing Arts Centre, though precise distances are unavailable.
The spacious 8-guest house boasts a fully equipped kitchen, air conditioning, a terrace, garden, parking, high-speed internet, two workspaces, and lake access with boat facilities (life jackets provided), making it ideal for families or groups.
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 3-br Retreat In The Berkshires - The Berkshires, MA
9.6 8 reviews

Lakefront 3-br Retreat In The Berkshires

apartment, Becket
This Becket lakeside property offers direct Pyramid Lake access and is located 3.7km from Jacob's Pillow dance centre.
The 149 square metre house sleeps six, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, a jacuzzi, terrace, garden, parking, and on-site hot tub.
Beautiful Berkshire Family Home - The Berkshires, MA
9.6 4 reviews

Beautiful Berkshire Family Home

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.

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.

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.
Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer! - The Berkshires, MA
No reviews

Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer!

apartment, New Marlborough
This six-bedroom, four-bathroom holiday home in Great Barrington is situated just 10 minutes from the town centre and under 10 minutes from Ski Butternut, offering convenient access to local amenities and outdoor pursuits.
This spacious property accommodates up to 14 guests and features a chef's kitchen, a heated seasonal swimming pool, a year-round hot tub, a game room, and a sauna, with a short hike from the grounds leading to a notable Berkshire view.
Lakefront Chalet | Dock, Sauna & Fireplace - The Berkshires, MA
9.0 2 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).
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.

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.

Bosworth Tap Room - The Berkshires, MA
9.9 100 reviews

Bosworth Tap Room

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.
Private Berkshires Home On 5+ Acres Rustic & Chic - The Berkshires, MA
No reviews

Private Berkshires Home On 5+ Acres Rustic & Chic

house, Otis
This private Berkshire home is located in Otis, just 21 kilometres from Cranwell Spa & Golf Club, 24 kilometres from Tanglewood, and 26 kilometres from both the Tanglewood Musical Center and the Norman Rockwell Museum, offering a peaceful retreat in the heart of the Berkshires. This spacious property spans 234 square metres, comfortably accommodating up to 10 guests with five bedrooms and three bathrooms. The house is equipped with modern amenities like air conditioning, a fireplace, a washing machine, and free Wi-Fi, as well as a fully equipped kitchen, a garden, a fitness centre, and parking.
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.
A Fun Country Escape For Two! Featuring A Fireplaces,hot Tub, And Ping Pong - The Berkshires, MA
9.8 140 reviews

A Fun Country Escape For Two! Featuring A Fireplaces,hot Tub, And Ping Pong

B&B, Sandisfield
This property is located in Sandisfield, just 20km from Questing, Dry Hill, Umpachene Falls Park, Beartown State Forest and Lake Buel, offering easy access to nature and outdoor activities. The house has received excellent ratings for its cleanliness, location and overall user experience.
The house is a spacious 51 square metre property with four bathrooms. The accommodation is equipped with a private pool, spa tub, barbecue grills, a fully equipped kitchen with a fridge, microwave, dishwasher, washer and dryer, and a Smart TV, ensuring a comfortable and enjoyable stay.

Best The Berkshires, MA holiday rentals with parking

Waterfront Oasis In Heart Of Berkshires - The Berkshires, MA
10 48 reviews

Waterfront Oasis In Heart Of Berkshires

apartment, Sandisfield
Berkshire Lakefront Cabin With Modern Luxuries - The Berkshires, MA
10 90 reviews

Berkshire Lakefront Cabin With Modern Luxuries

apartment, Otis
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.8 47 reviews

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

apartment, Otis
Lux On The River Near Tanglewood W/220v Ev Charge - The Berkshires, MA
9.9 93 reviews

Lux On The River Near Tanglewood W/220v Ev Charge

apartment, Sandisfield
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