Search vacation rental in Monterey, MA from 100+ sites!

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

Services and facilities include a fridge, a kitchen and a freeze. This accommodation in Monterey also has a gym!

About: Vacation rental for 2 guests with an excellent rating of 100% based on 25 reviews. You will be based in Sheffield.

Services and facilities include air conditioning, a fridge and a coffee place. This apartment in Sheffield also has a garden!

About: This apartment is located in Monterey, between Great Barrington, Stockbridge, and Lenox, minutes from the Appalachian Trail and Butternut for skiing.

This apartment has excellent user, location, and cleanliness ratings.

It has 2 bedrooms, 1 bathroom, and can accommodate up to 5 guests.

This apartment offers a fully stocked kitchen with high-quality appliances, super fast fiber wireless internet connection, a converted garage into a full gym with yoga/stretching area, custom-made furnishings and decor, and two bikes available for guest use.

About: Cottage for up to 4 guests with an excellent rating of 97% based on 27 reviews. You will stay in New Marlborough.

Facilities and services: a fridge, free parking and a freeze. This accommodation in New Marlborough also has a garden!

About: Charmingly situated in the heart of Otis, this family-friendly cottage offers a peaceful retreat just steps away from the city center and its many attractions.

With excellent ratings for location, cleanliness, and user experience, this one-bathroom cottage comfortably accommodates up to eight guests, providing ample space for families or groups of friends.

Fully equipped with modern amenities including air conditioning, a Jacuzzi, and a well-stocked kitchen, this cottage ensures a comfortable and memorable stay. Guests can enjoy the tranquility of the private garden and take advantage of nearby activities such as hiking, biking, and exploring the town's rich history.

About: House with an excellent rating of 99% based on 61 reviews. You will be located in New Marlborough.

Facilities and services include a kitchen, free parking and a fridge. Take advantage of the terrace in this house in New Marlborough.

About: Cabin for 10 people with an excellent rating of 93% based on 25 reviews. You will stay in Great Barrington.

Services and facilities include a fridge, a freeze and a dish washer. Take advantage of the garden in this accommodation!

About: Secluded yet close to everything, this mountain cabin is a short drive from Lake Buel, Ski Butternut and Les Trois Emme Winery.

Excellently rated, it's a spacious 4-bedroom cabin with 2 bathrooms and a guest capacity of 10.

Enjoy a cozy fireplace, a fully equipped kitchen, a serene garden with barbecue grills, a balcony and air conditioning.

About: Vacation rental with an excellent rating of 100% based on 10 reviews. You will be located in Lee.

Services and facilities include free parking, a terrace and a fridge. This apartment in Lee also has air conditioning!

About: House rental for 10 people with an excellent rating of 85% based on 12 reviews. This accommodation is located in Sheffield.

Facilities and services include a dish washer, a foosball and a garden. Take advantage of the Free Parking with this accommodation in Sheffield!

About: This apartment is located in Becket, a town in the Berkshires, 5 minutes from Jacob's Pillow and 25 minutes from Tanglewood.

It has an excellent user rating, location rating and cleanliness rating.

The apartment has 6 bedrooms and 4 bathrooms, a vaulted ceiling, a full kitchen, a relaxing hot tub, a cozy fire pit, a spacious yard for outdoor activities, a dedicated study with a twin bed in the atrium, a spacious basement with a ping pong table and wildlife sightings in the surrounding rural area.

About: House listing for 4 people with an excellent rating of 90% based on 1 reviews. Your accommodation will be based in Sandisfield.

Services and facilities: a child space, a dish washer and a terrace. You can bring your favorite pets this house!

About: This apartment is in the heart of Monterey, surrounded by beautiful gardens and just steps away from the beach. It has excellent user, location, and cleanliness ratings.

The apartment has 3 bathrooms and can accommodate up to 6 guests. It features a fully equipped kitchen, a garden, and parking. It is pet-friendly and family-friendly, and it has internet access.

Guests can enjoy the nearby Cannery Row, Fisherman's Wharf, and the Monterey Bay Aquarium.

About: Mill rental from 298 dollars for 6 guests with an excellent rating of 100% based on 1 reviews. You will be located in Great Barrington.

Services and facilities include air conditioning, a garden and a barbecue. Take advantage of the Spa in this accommodation!

About: Cabin rental for up to 6 people with a good rating of 80% based on 2 reviews. You will stay in Otis.

Services and facilities include a fridge, a kitchen and free parking. Pets are welcome in this accommodation.

About: Located in the heart of the Berkshires, this secluded cabin is just 15 miles from the Norman Rockwell Museum and 16 miles from Tanglewood. The location offers a peaceful retreat surrounded by nature, while still being close to cultural attractions.

With an excellent user and location rating, this cabin is a popular choice for travelers.

The cabin has three bedrooms, two bathrooms, and a floor area of 1450 square feet, comfortably accommodating up to six guests.

The fully equipped kitchen, free Wi-Fi, and proximity to hiking trails and other outdoor activities make this cabin an ideal choice for a relaxing and enjoyable getaway.

About: This cabin is located in Otis, a town in the Berkshires of Western Massachusetts, near Otis Ridge and Butternut Ski Resort (10-mile drive), and Lee Premium Outlets (10-mile drive). It has an excellent user rating.

The cabin has a floor area of 1450 square feet and can accommodate up to 6 guests. It has 3 bedrooms and 2 bathrooms.

The cabin is located on a secluded 25-acre property with panoramic views. It has direct access to hiking trails and a private pond. The cabin has a cozy interior with a wilderness theme. It has a fully equipped kitchen and multiple dining areas. The spacious living room has streaming services. The cabin also has a private washer/dryer and high-speed internet. Outside, there are Adirondack chairs for relaxation overlooking Royal Pond.

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About: This chalet is situated in New Marlborough, surrounded by protected woods and wetlands, a peaceful natural setting. Close to Sheffield and Great Barrington for amenities and attractions.

This 4-bedroom, 2-bathroom chalet can accommodate up to 8 guests, making it ideal for families or groups.

Amenities include a fully equipped kitchen, stunning full wall of windows overlooking nature, enclosed screened porch with fireplace, cozy living room with wood stove, thoughtful kitchen design with breakfast bar, spacious dining room with repurposed bowling lane table, four bedrooms, including a primary suite with balcony, recreation room with exercise equipment and ping pong table, home office setup in one bedroom, and more.

About: Cottage from 149 dollars for 5 guests. Your accommodation will be located in Lee.

Facilities and services include a kitchen, free parking and air conditioning. This is a pet-friendly accommodation!

About: Vacation rental listing at 383 dollars for 6 people. You will stay in Becket.

Services and facilities: a fridge, a terrace and a washing machine.