Holiday Rentals in The Berkshires

This charming guesthouse is situated in Southfield, a small village just 10km from Great Barrington, offering a peaceful retreat in the heart of the Berkshire countryside. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The guesthouse has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a king-size bed, a claw-foot bath, and a loft-style bedroom, making it ideal for a relaxing getaway. Guests can enjoy a range of nearby attractions, including Ski Butternut, hiking trails, and local restaurants, all within easy reach.

This family-friendly holiday home is situated near Monterey, within a 3km radius of Beartown State Forest and Bidwell House Museum, and within 10km of Ashintully Gardens and McLennan Reservation. The property has received excellent ratings for its cleanliness, location and user experience.
The accommodation has four bedrooms and a floor area of 288 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a fireplace, a patio with a barbecue grill, a fitness centre, and a garden.

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.

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.

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.

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.

This five-bedroom Becket lakeside property, near Pyramid Lake (0.6km) and Jacob's Pillow Dance Festival (2.9km), offers stunning waterfront views and easy access to Iroquois Waterfront and Becket Quarry (within 9.6km).
The 223 square metre house boasts a fully equipped kitchen, two bathrooms, a jacuzzi, private balcony, and parking, comfortably accommodating up to ten guests.

This renovated barn, a short drive (less than 2km) from Monterey Town Beach in Monterey, Massachusetts, provides easy access to Tanglewood, Butternut Ski Area, and the Appalachian Trail.
The 167 square metre property features two bedrooms, one bathroom, sleeping up to six guests, and includes a kitchen with microwave, air conditioning, a terrace, garden, parking, and Wi-Fi.

This chalet is located just 20km from Tanglewood, nestled in the tranquil forest setting of Otis, Berkshire County, Massachusetts. The property has received excellent ratings for its cleanliness, location, and user experience.
The chalet has five bedrooms, a cosy loft, and can accommodate up to ten guests. It offers a range of amenities, including a fully equipped kitchen, a home office with high-speed WiFi, a Tesla-compatible charger, and a unique Nordic experience with an exterior barrel sauna.

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.

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).

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.

This rustic modern apartment is located in Otis, Massachusetts, just 5 kilometres from Otis Ridge Ski Area and within a 15-kilometre radius of Butternut and Catamount ski resorts, perfect for a winter getaway. The property has received excellent ratings for its cleanliness, location and overall experience.
The apartment can accommodate up to 6 guests and features a spacious layout with a modern kitchen, a cosy fireplace and a large garden. Guests can enjoy the convenience of a fully equipped kitchen, a washer and dryer, and a wrap-around deck with a gas grill, as well as access to a range of activities in the surrounding area, including skiing, hiking and exploring the Berkshires.

This one-bedroom cabin in New Marlborough is situated beside the Umpachene River, a short distance from the Appalachian Trail and the town centre.
The cabin is equipped with a well-equipped kitchen, a private sauna, and an outdoor shower, comfortably accommodating up to four guests.

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.

This five-bedroom chalet is situated in Otis, Massachusetts, approximately 30 kilometres from Cranwell Spa & Golf Club and 34 kilometres from Tanglewood.
The 242 square metre property features a fully equipped kitchen, three bathrooms, a sauna and a patio, comfortably accommodating up to 14 guests.