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

About: This apartment is located in the heart of Lenox's entertainment district, within easy reach of major attractions. It has very good user ratings and excellent location and cleanliness ratings.

The condo features a fireplace, free WiFi, a fully equipped kitchen, and cable TV. Guests have access to a fitness center, spa services, indoor and outdoor pools, an outdoor tennis court, and a sauna.

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About: Chalet listing for 8 guests with an excellent rating of 100% based on 10 reviews. You will be based in Monterey.

Services and facilities include a fridge, air conditioning and a kitchen. Take advantage of the Free Parking with this accommodation in Monterey!

About: Holiday Inn Club Vacations Oak N’ Spruce Resort In The Berkshires, An Ihg Hotel is located in the heart of the Berkshires. It is a 4-star resort with a very good user rating and excellent location and cleanliness ratings. The resort is close to Beartown State Forest, Housatonic River, Berkshire Theatre Festival and Schantz Galleries. It offers amenities such as 2 indoor pools, 2 outdoor pools, a fitness center, a tennis court, a sauna, a concierge, a restaurant, a bar, and free parking.

About: Vacation rental for 13 people with an excellent rating of 98% based on 85 reviews. You will be in Stockbridge.

Facilities and services include an iron, a dish washer and a barbecue. Take advantage of the Free Parking with this accommodation in Stockbridge!

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About: This 4-bedroom, 2-bathroom apartment is located in the peaceful town of Otis, surrounded by verdant woods and offers convenient access to popular Berkshire attractions. With excellent user, location, and cleanliness ratings, this family-friendly apartment provides a tranquil escape for up to 8 guests.

The apartment boasts an open living and dining area, a private master suite with an en-suite bathroom, a fully equipped kitchen, and a versatile loft that can be used as additional sleeping or playroom space. Guests can enjoy the outdoors in the garden, prepare meals on the gas grill, or observe local wildlife from the comfort of the property. The apartment also includes Wi-Fi, a washer and dryer, and an office area for remote work or study.

About: This cabin is located in a peaceful and serene area of Sandisfield, within a short distance of Otis Ridge, Ashintully Gardens, and McLennan Reservation. It has excellent user, location, and cleanliness ratings.

The cabin has a floor area of 1980 square feet and can accommodate up to 10 guests in its 4 bedrooms. It features a spacious garden, a barbecue grill, a cozy fireplace, a fully equipped kitchen, a comfortable sofa bed, a DVD player, a spa, a tennis court, and parking.

About: Apartment rental for up to 16 people with an excellent rating of 95% based on 60 reviews. This accommodation is based in Lee.

Services and facilities: an iron, a garden and a sauna. This apartment also has air conditioning!

About: This cottage is situated in the historic district of New Marlborough, within walking distance of the Inn on The Green and New Marlborough Grange. It has an excellent user rating.

The cottage has 1 bedroom, 1 bathroom, a sleeping loft for two, and a queen-size sleeper sofa for additional guests. It has a floor area of 1190 square feet and can accommodate up to 4 guests. It has a full kitchen and bath, a 1,000 sq ft cedar deck on three sides, a Goshen stone patio, a grilling area, and a 140' rock wall that accentuates the property. It also features air conditioning, internet, a fridge, a garden, and parking. Pets are allowed, and it is family-friendly.

About: Apartment rental listing for 4 guests with an excellent rating of 95% based on 182 reviews. You will be in Otis.

Facilities and services: a washing machine, a fridge and a dish washer. Take advantage of the Free Parking with this accommodation in Otis!

About: Accommodation for up to 6 guests with an excellent rating of 95% based on 97 reviews. You will be in Becket.

Facilities and services: a garden, free parking and a dish washer.

About: Book this vacation rental for up to 2 people with an excellent rating of 98% based on 122 reviews. Your accommodation will be based in Sandisfield.

Facilities and services include a barbecue, a child space and a coffee place. You can also relax in the jacuzzi!

About: This 3-bedroom apartment rental in Sandisfield, Massachusetts provides a secluded setting surrounded by 8 acres of pristine nature and the Buck River. It's conveniently located near ski resorts, cultural venues, and natural attractions.

The apartment has an excellent user, location, and cleanliness ratings. It features a spacious open floor plan with a fireplace, baby grand piano, and multiple dining areas. The master bedroom has a private deck and luxurious bathroom. It can accommodate up to 6 guests and has an in-ground pool, screened porch, and proximity to hiking, horseback riding, canoeing, and skiing.

About: Cabin for 12 guests with an excellent rating of 97% based on 41 reviews. You will be located in Sandisfield.

Services and facilities include a swimming pool, a barbecue and a washing machine. This accommodation is ideal for families.

About: This Monterey cabin is a peaceful retreat on a private 2-acre lot with beautiful woods and a babbling brook, just minutes from Ski Butternut, Catamount, Tanglewood, Lenox, and Great Barrington. With excellent user, location, and cleanliness ratings, this spacious and comfortable cabin offers four upstairs bedrooms, a modern kitchen, a screened porch, and a floor area of 2500 square feet.

Guests can enjoy a relaxing soak in the outdoor hot tub, roast marshmallows by the fire pit, or grill on the oversized gas grill. The cabin also features a well-stocked kitchen, a selection of DVDs, games, and books, and even kayaks for exploring Lake Garfield.

About: Apartment listing for up to 7 guests with an excellent rating of 97% based on 154 reviews. You will be based in Otis.

Facilities and services include a dish washer, a jacuzzi and a fridge. This apartment in Otis also has air conditioning!

About: Accommodation for up to 4 guests with an excellent rating of 97% based on 395 reviews. You will stay in Otis.

Services and facilities include a fridge, free parking and a washing machine. Take advantage of the garden in this accommodation in Otis.

About: Cabin for up to 15 people with an excellent rating of 99% based on 176 reviews. You will be located in Otis.

Services and facilities: a dish washer, a washing machine and free parking.

About: This Otis apartment offers a unique secluded location on 60 acres of private woodland with hiking trails, only 3 miles away from Otis Town Beach. The apartment has excellent user, location, and cleanliness ratings.

This 2-bedroom, 2-bathroom apartment can accommodate up to 5 guests. It features a newly renovated kitchen, a screened-in porch with dining and seating areas, air conditioning, a garden, and parking. Guests can also enjoy amenities such as a fridge, microwave oven, and dishwasher.

About: Book this vacation rental for up to 6 people with an excellent rating of 99% based on 38 reviews. This accommodation is located in Otis.

Facilities and services: an access for persons with reduced mobility, a washing machine and air conditioning. This is a family-friendly apartment!

About: Secluded Retreat is a family-friendly accommodation just a short drive from Monterey's attractions. It's surrounded by 8 secluded woodland acres, close to Lake Garfield, Beartown State Forest, and Cantina. The house has excellent ratings for location, cleanliness, and user experience.

The accommodation has a modern loft design with 3 bedrooms, 2 bathrooms, and a guest capacity of 8. It features a fully equipped kitchen, a TV with a DVD player, reliable Wi-Fi, a wood stove, and a deck with tranquil woodland views. Guests can also enjoy hiking trails from the house to Dry Hill and Steeple Top trails, and indulge in local delicacies from nearby farms.

About: This Otis cottage is a family-friendly accommodation with an excellent user rating and location. It has a garden, parking, and air conditioning.

The cottage has one bathroom and can accommodate up to 8 guests. It features a kitchen with a fridge, freezer, microwave oven, and dishwasher. It also has a Jacuzzi.

About: Apartment rental for 6 guests with an excellent rating of 99% based on 42 reviews. This accommodation is located in New Marlborough.

Services and facilities: a kitchen, air conditioning and a washing machine. Enjoy free parking with this accommodation in New Marlborough!

About: Apartment listing for 10 people with an excellent rating of 93% based on 18 reviews. You will be in New Marlborough.

Facilities and services include a dish washer, a kitchen and free parking. Take advantage of the garden in this apartment in New Marlborough.

About: This 1754 historic house is nestled in the southeast corner of the Berkshires in Sandisfield, MA, about a half hour drive from shopping. The home has excellent user ratings for location, cleanliness, and overall experience.

The house has 4 bedrooms, 1 bathroom, and a guest capacity of 6. It features wide plank floors, historic details, eclectic antique furniture, updated mechanicals, insulation, and foundation; original floor restoration. Guests can immerse themselves in American history and enjoy the charm of a historic colonial house.

About: Apartment rental for 5 guests with an excellent rating of 94% based on 20 reviews. This accommodation is located in Monterey.

Facilities and services: an iron, a garden and a fitness center. Pets are welcome in this apartment.

About: Apartment rental for 4 people with an excellent rating of 97% based on 20 reviews. Your accommodation will be based in Monterey.

Facilities and services include free parking, a fridge and a barbecue.

About: Cabin rental for 5 people with an excellent rating of 98% based on 82 reviews. This accommodation is located in New Marlborough.

Facilities and services: a coffee place, a fridge and a kitchen. You can bring your favorite pets this accommodation!

About: This spacious farmhouse in Otis is located in a peaceful rural setting, yet close to cultural attractions and amenities. It has received excellent user ratings for its location, cleanliness, and overall experience.

The farmhouse features four bedrooms (two king, two queen) and 2.5 bathrooms, accommodating up to eight guests. The well-equipped kitchen has high-quality appliances and cookware for cooking enthusiasts. Amenities include air conditioning, a garden, and pet-friendliness. Guests have access to hiking trails, swimming spots, and cross-country skiing within 10-30 minutes.

About: This charming cottage in the hills of Monterey offers a secluded and peaceful retreat, just minutes from Lake Garfield and the town center. With excellent user, location, and cleanliness ratings, this cottage is a great choice for travelers seeking a cozy and comfortable stay.

The cottage features three spacious bedrooms, including a master suite with access to the main bathroom, and a cozy sitting room with ample windows overlooking the scenic mountain landscape. It also boasts a traditional wood great room with a fireplace, a newly renovated kitchen, and a garden. Guests can enjoy the surrounding nature, encounter wildlife, and relax in the rustic ambiance of an old hunting lodge.