Compare vacation rentals in The Berkshires, MA from 100+ sites!

3329 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
The Berkshires, MA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in The Berkshires, MA

Best The Berkshires, MA vacation 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 lakefront house in Monterey, Massachusetts, is located near Lake Garfield, offering easy access to the Bidwell House Museum and Mahaiwe Performing Arts Center in the Berkshires.
This 1990-square-foot vacation rental boasts three bedrooms, two bathrooms, and sleeps six, featuring a spacious deck, private docks with kayaks, and a den/gameroom.
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
This vacation home is located in the mountains, just half a mile from Otis Ridge and within a 6-mile radius of County Beach and Ashintully Gardens, offering a peaceful retreat surrounded by natural beauty. The property has received excellent user ratings, indicating a high level of satisfaction among previous guests. This 3-bedroom home offers 1650 square feet of space and comfortably accommodates up to 7 guests. The home features a fully equipped kitchen, a relaxing Jacuzzi, a private garden with barbecue grills, and stunning mountain views, providing everything you need for a comfortable and enjoyable stay.
Scribe`s Stable | A/c  Screened In Porch  Sleeps 6 - The Berkshires, MA
10 4 reviews

Scribe`s Stable | A/c Screened In Porch Sleeps 6

manor house, Monterey
This renovated barn, a short drive from Monterey Town Beach and near Tanglewood, Butternut Ski Area, and Great Barrington, offers a peaceful retreat in Monterey, Massachusetts.
This 1800-square-foot farmhouse features two bedrooms, one bathroom, and can accommodate six guests, boasting a rustic-modern design with vaulted ceilings, exposed beams, a kitchen with a microwave, air conditioning, a terrace, and ample parking.
Garfield Grounds | Lakeside  Guest Cottage  Dock - The Berkshires, MA
10 1 review

Garfield Grounds | Lakeside Guest Cottage Dock

apartment, Monterey
This lakeside Monterey, Massachusetts vacation home, near Lake Garfield, offers easy access to Otis Ridge, Les Trois Emme Winery, McLennan Reservation, and Dry Hill.
This 4,040-square-foot property features four bedrooms, three bathrooms, a private dock on Lake Garfield, a spacious main house with a fireplace, a separate guest house with a wood stove, a basement TV room, and can accommodate up to ten guests.

Search Family Vacation Rentals in The Berkshires, MA

Enjoy the fresh air and nearby hiking trails when you stay at these family-friendly vacation rentals in The Berkshires, MA.

Berkshires Cabin 2 Mi To Appalachian Trail! - The Berkshires, MA
9.6 45 reviews

Berkshires Cabin 2 Mi To Appalachian Trail!

cabin, Otis
Berkshires Cabin is an excellent cabin rental in Otis, located just 2 miles from the Appalachian Trail. It has received excellent ratings for its location, cleanliness, and user experience.
The cabin features 3 bedrooms, 2 bathrooms, a fully equipped kitchen, and a cozy living area. It can accommodate up to 7 guests and offers amenities such as free Wi-Fi, a flat-screen TV, a dishwasher, a microwave, a fridge, and a spa. Guests can also enjoy the outdoor space with a deck or patio area.
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
This 3-bedroom apartment is located in Otis, Massachusetts, just a short walk from the Otis Ridge Ski Area and a 20-minute drive from the town of Great Barrington. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment features a spacious living area with a fireplace and a pull-out couch, accommodating up to 7 guests. It comes equipped with a private hot tub, a large deck, a fully equipped kitchen, and access to a variety of outdoor activities, including hiking trails and lakes.
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 located in New Marlborough, just a short drive from Great Barrington and Ski Butternut, making it the perfect base for exploring the Berkshires. The house has received excellent ratings for its location, cleanliness, and overall experience.
This contemporary home features 5 bedrooms and 4 bathrooms, comfortably accommodating up to 12 guests. Casa Mia offers a variety of amenities for relaxation and recreation, including a swimming pool, hot tub, sauna, and a spacious garden with a fire pit and bocce court.
Iconic Lodge In The Berkshires - The Berkshires, MA
9.7 64 reviews

Iconic Lodge In The Berkshires

cabin, Sandisfield
This Sandisfield cabin is located in the Berkshires, a scenic region of western Massachusetts, just a short drive from popular destinations like Stockbridge, Great Barrington, and Tanglewood. The cabin has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travelers seeking a comfortable and enjoyable stay.
This charming home features four bedrooms, two lofts, and a spacious layout, accommodating up to 12 guests. Amenities include a massive stone fireplace, a modern kitchen, a billiards lounge, an indoor swimming pool, a yoga room, and a private setting with ample parking.

Frequently Asked Questions about vacation 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. Their collection of Impressionist and Post-Impressionist art is world-class, and the grounds are beautiful. You should also check out the Tanglewood Music Center in Lenox, which is home to the Boston Symphony Orchestra in the summer. It's a great place to enjoy a concert under the stars.
  • What are the best Airbnb and vacation rentals in The Berkshires, MA?

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

    Stockbridge is a charming town with lots of shops, restaurants, and art galleries. It's also close to many of the Berkshires' most popular attractions. If you're looking for something a little more secluded, you could consider a rental in the town of Great Barrington, which is known for its beautiful scenery and relaxed atmosphere.
  • What are the most popular Airbnbs in The Berkshires, MA?

    Among the Airbnbs in The Berkshires, MA, Peace And Quiet On The Lake, Victorian Manor 5 Bathrooms and Ski Berkshire Get Away In Gb are the most popular ones.

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

    The Berkshire Museum in Pittsfield has a great dinosaur exhibit that kids love. The Hancock Shaker Village in Pittsfield is also a popular spot for families, with its historic buildings and working farm. And for a fun day out, you can't beat the Berkshire Scenic Railway in Lenox, which offers scenic train rides through the countryside.
  • What are the best vacation rentals with a pool in The Berkshires, MA?

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

    If you're looking for the best deals, you should book your rental in the off-season, which is typically from November to April. However, if you want to experience the Berkshires in all its glory, you should book during the peak season, which is from May to October. Keep in mind that prices will be higher during the peak season.
  • 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 Jacob's Pillow Dance Festival in Becket is a must-see for dance enthusiasts. The Berkshire Botanical Garden in Stockbridge hosts a variety of events throughout the year, including its annual Plant Sale in the spring. And for a taste of local culture, check out the Great Barrington Farmers Market, which runs from June to October.
  • What are the best rentals or Airbnbs with a jacuzzi in The Berkshires, MA?

    The best vacation rentals or Airbnb with a jacuzzi in The Berkshires, MA are The Meadows House @ Otis Ridge W/ 7-person Hot Tub, The Freckled Hen's Berkshire Nest and Sweet Dreams Retreat.

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

    Take a scenic drive along the Mohawk Trail, which winds its way through the Berkshires, offering stunning views of the mountains and forests. Hike or bike the Appalachian Trail, which passes through the Berkshires. Visit the free exhibits at the Norman Rockwell Museum in Stockbridge, which showcases the iconic American artist's work.
  • What are the best restaurants with local dishes in Monts Berkshire?

    The Red Lion Inn in Stockbridge is a historic restaurant with a menu of classic New England dishes. For a more casual dining experience, try the The Wheatberry in Great Barrington, which serves up delicious farm-to-table fare. If you're looking for something a little more upscale, you can't go wrong with the Allium in Lenox, which offers a modern American menu with a focus on local ingredients.
  • What are the best walking or cycling routes in Monts Berkshire?

    The Ashuwillticook Rail Trail is a 10-mile paved path that follows the former Ashuwillticook Railroad line. It's a great place for walking, biking, or rollerblading. The Taconic Crest Trail is a 36-mile hiking trail that runs along the Taconic Range, offering stunning views of the surrounding countryside. For a more challenging ride, try the 100-mile Berkshire Scenic Byway, which winds its way through the Berkshires, offering views of the mountains, forests, and lakes.
  • Are there pet-friendly attractions in Monts Berkshire?

    The Berkshires are a very dog-friendly area. Many of the hiking trails and parks are open to dogs, and there are also a number of pet-friendly restaurants and hotels. The Hopkins Memorial Forest in Williamstown is a great place to take your dog for a walk. The Mount, Edith Wharton's former estate in Lenox, is also pet-friendly, and you can enjoy a walk around the grounds 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 they are often located in more desirable locations, such as near hiking trails or lakes. They also tend to be more affordable than hotels, especially for families or groups of friends. You can often find vacation rentals that are pet-friendly, which is a big plus for travelers with furry companions.
  • What are the top sports attractions and facilities in Monts Berkshire?

    The Berkshires are a great place for outdoor sports enthusiasts. The area has many hiking trails, biking paths, and ski resorts. The Butternut Ski Area in Great Barrington is a popular spot for skiing and snowboarding. The Jiminy Peak Mountain Resort in Hancock is another popular option, offering skiing, snowboarding, and snow tubing. The Berkshires are also home to a number of golf courses, including the Wyantenuck Country Club in Great Barrington and the Cranwell Resort & Golf Club in Lenox.

Popular destinations

Best The Berkshires, MA vacation rentals with a fireplace

Light-filled Cottage - The Berkshires, MA
10 4 reviews

Light-filled Cottage

apartment, New Marlborough
This New Marlborough woodland cottage, situated on a scenic dirt road near numerous lakes and waterfalls, offers a secluded escape for nature lovers.
The 4-bedroom, 1-bathroom house sleeps 5, features a fully equipped kitchen with dishwasher, high-speed internet, a wood-burning stove, and ample outdoor space including a deck and lawn suitable for tent pitching; nearby cafes and restaurants provide convenient dining options.
Cozy Escape In The Trees Of The Berkshires - The Berkshires, MA
9.5 23 reviews

Cozy Escape In The Trees Of The Berkshires

apartment, New Marlborough
This 5-bedroom apartment is located in New Marlborough, a short distance from scenic hikes, swimming lakes, and winter skiing opportunities. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment features a private and spacious backyard, perfect for entertaining. This home is fully stocked and comes with a fireplace, barbecue grill, trampoline, tire swing, soccer net, and a fully equipped kitchen.
4 Acres | Rustic-modern Berkshires Retreat - The Berkshires, MA
9.8 159 reviews

4 Acres | Rustic-modern Berkshires Retreat

apartment, Otis
Otis apartment is a family-friendly accommodation with excellent ratings for its location, cleanliness, and user experience. It is a 1-bathroom apartment with a guest capacity of 6, and has a kitchen with a fridge, freezer, microwave oven, and dishwasher.
The apartment is air-conditioned and has a garden and parking. It also has internet access.
Exotic Mountain Retreat In The Berkshires. - The Berkshires, MA
9.8 208 reviews

Exotic Mountain Retreat In The Berkshires.

cabin, Otis
This peaceful cabin in the Berkshire Mountains is just 15 minutes from Butternut Ski Mountain and the town of Great Barrington. It has excellent user, location, and cleanliness ratings. This spacious 5-bedroom, 4-bathroom cabin comfortably sleeps 15 guests. You'll enjoy modern amenities like full 5G WiFi, a gas BBQ and blacktop grill, a coffee pot, a latte maker, a Keurig, and AC units in the main living room, master bedroom, and two upstairs bedrooms.

Best The Berkshires, MA vacation rentals with a sauna

Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires, MA
9.9 186 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

cabin, New Marlborough
This one-bedroom cabin is located in New Marlborough, Massachusetts, near the Umpachene River and a short drive from the town center.
The cabin, which sleeps up to four guests, offers a private sauna, a cozy fire pit, and access to hiking trails in the surrounding forest.
Forget-me-not By Avantstay - The Berkshires, MA
No reviews

Forget-me-not By Avantstay

house, Monterey
This Monterey vacation rental is located 14 miles from Cranwell Spa & Golf Club and 15 miles from the Norman Rockwell Museum, offering easy access to area attractions. The home provides a peaceful retreat in a tranquil setting.
The house has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a fireplace, a jacuzzi, and a lakefront location.
Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires, MA
9.8 69 reviews

Forget-me-not By Avantstay | Bold Lakefront Escape

apartment, Monterey
This Monterey apartment is located in the Berkshires, a scenic region in western Massachusetts, with Lake Garfield just steps away. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The home has a modern design with a lofted interior and a large deck overlooking Lake Garfield. This three-story retreat comfortably accommodates up to 12 guests and includes amenities like a hot tub, ping pong table, and cornhole set, as well as a fully equipped kitchen.
Sunset Falls Estate, 167 Private Acres, Berkshires - The Berkshires, MA
10 3 reviews

Sunset Falls Estate, 167 Private Acres, Berkshires

apartment, New Marlborough
Sunset Falls, a luxurious mountain estate in the Berkshires of western Massachusetts, is located 20 minutes from Great Barrington, offering seclusion on 167 private acres with breathtaking mountain views.
This 6-bedroom, 6-bathroom mansion sleeps 14 guests and boasts a chef's kitchen with Sub-Zero and Wolf appliances, a fitness center, jacuzzi, sauna, spa, bar, extensive game room, and concierge services including in-house massage and chef options.

Choose the Right Luxury Vacation Rentals in The Berkshires, MA

Experience luxury at its finest with a vacation rental or Airbnb in The Berkshires, MA selected for its quality and breathtaking surroundings.

Berkshires Retreat W Magic View! 
Beach/swim 1 Mi! - The Berkshires, MA
9.8 149 reviews

Berkshires Retreat W Magic View! Beach/swim 1 Mi!

apartment, Monterey

Guest-Favorite Pet-Friendly Vacation Rentals in The Berkshires, MA

Explore the peaks with your pet from These dog-friendly vacation rentals and Airbnbs in The Berkshires, MA, situated near pet-friendly trails.

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
Cozy Cabin In The Berkshires - The Berkshires, MA
10 20 reviews

Cozy Cabin In The Berkshires

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

Bidwell Landing | Lakefront Spacious

apartment, Monterey

Top-Rated Vacation Rentals with Swimming Pool in The Berkshires, MA

Relax after an active day with a refreshing dip at one of these vacation rentals with a pool 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
Quintessential 6-br Berkshires Lodge - The Berkshires, MA
9.7 134 reviews

Quintessential 6-br Berkshires Lodge

apartment, Becket
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
Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 16 reviews

Berkshires Oasis Retreat: Art Meets Nature

apartment, Otis

Discover Vacation Rentals with Jacuzzi in The Berkshires, MA

Nothing beats coming home to a hot tub after a day of hiking in The Berkshires, MA.

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
Berkshires Waterfront Escape W/ Hot Tub & Kayaks - The Berkshires, MA
10 30 reviews

Berkshires Waterfront Escape W/ Hot Tub & Kayaks

apartment, Otis
Bosworth Tap Room - The Berkshires, MA
9.9 100 reviews

Bosworth Tap Room

apartment, Sandisfield
Lakefront Otis Home W/ Stunning Views & Boats! - The Berkshires, MA
10 16 reviews

Lakefront Otis Home W/ Stunning Views & Boats!

apartment, Otis
©2026 cozycozy.com