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This Pittsfield apartment is conveniently located near both South and North County attractions, including Mass MoCA, the Clark Institute, and Tanglewood, making it a great base for exploring the Berkshires. The apartment has earned excellent ratings for its cleanliness, location, and user experience.
The apartment features a spacious living and dining area, perfect for relaxing after a day of exploring, and comfortably accommodates up to four guests. Amenities include a screened-in porch, a shared backyard, a well-equipped kitchen, a modern bathroom, driveway parking, and laundry access.

This waterfront vacation home on Onota Lake in Pittsfield offers direct access to water sports and is located within 3 miles of Tanglewood Music Center, Crane Museum of Papermaking, and Colonial Theater, with Bousquet Ski Area just 2 miles away.
This 1800 square foot house features 3 bedrooms, 2 bathrooms, sleeps 10, and includes a modern kitchen with a fridge, microwave, and dishwasher, plus a private dock and a large covered deck for outdoor enjoyment.

This 4-bedroom, 4-bathroom apartment is located in Pittsfield, Massachusetts, within a mile of Bousquet Ski Area and Guido's Marketplace, making it ideal for families or groups of up to 8 people looking for a convenient location near outdoor activities and shopping. The apartment features a fully equipped kitchen, a fireplace, a Smart TV with a DVD player, a fitness center, and a swimming pool, providing a comfortable and enjoyable stay for guests.

This mid-century modern vacation rental in Pittsfield, near Hancock Shaker Village, offers easy access to Pittsfield attractions like Bousquet Ski Area and the Berkshire Museum.
The three-bedroom, two-bathroom home features a fully equipped kitchen with a fridge, microwave, and dishwasher; high-speed Wi-Fi; air conditioning; and parking, all within a unique design inspired by Frank Lloyd Wright on six private acres with hiking trails and ponds.

This Pittsfield vacation home offers convenient access to the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, all within a 10-minute walk, and is less than a mile from the Housatonic River and Barrington Stage Company.
This 3,300-square-foot house features seven bedrooms, two bathrooms, accommodates nine guests, and includes a fully equipped kitchen, fireplace, in-house washer, private garden, balcony, and parking.

This one-bedroom apartment is located just a short distance from Jiminy Peak Mountain Resort, making it a perfect choice for skiers and snowboarders. The apartment is also conveniently close to other attractions like Zema's Nursery and Pittsfield State Forest, offering plenty of opportunities for outdoor exploration. The apartment has received excellent user ratings, indicating a high level of satisfaction among previous guests.
The apartment features a comfortable living space with a sofa bed, accommodating up to 5 guests. Enjoy a range of amenities including a fully equipped kitchen, a private terrace or balcony, a swimming pool, a fitness center, and a garden, ensuring a relaxing and enjoyable stay.

This 2-bedroom, 1-bathroom rental in Richmond, located in The Berkshires, offers private community beach access on Richmond Pond and is a short walk from the water.
This apartment features a wood-burning fireplace, a newly renovated kitchen with a refrigerator and microwave, and includes a tandem kayak for guest use, with proximity to Tanglewood and Bousquet ski area for entertainment.

This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.

This Pittsfield vacation home offers a central location, within a 10-minute walk of the Berkshire Athenaeum, Colonial Theatre, and Berkshire Museum, and less than a mile from the Barrington Stage Company and the Housatonic River.
This four-bedroom, two-bathroom house sleeps seven and features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and a coffee/tea maker, plus a Smart TV, in-unit laundry, and on-site parking.

This house is located in Lenox, just a short walk from The Bookstore and a short drive from Tanglewood Music Center. This vacation rental has excellent user ratings, making it a popular choice for travelers.
The house has 3 bedrooms and 3 bathrooms, accommodating up to 6 guests. It offers modern conveniences, a private patio, a garden, and a barbecue grill, making it ideal for a relaxing and enjoyable stay.

This 3rd-floor penthouse, located on a quiet street in Pittsfield, offers convenient access to North Street's dining, shopping, and cultural attractions, and is a short drive to Tanglewood.
This 3-bedroom, 1-bathroom condo accommodates up to 6 guests and features original stained-glass windows, a rooftop deck, a stone terrace, and an open-plan living and kitchen area.

This 5-bedroom vacation rental is conveniently located just minutes from downtown Pittsfield, a short drive from the Berkshires' beauty and attractions, and only 7 miles from the renowned Tanglewood music venue.
This spacious home features a fully equipped kitchen, a fireplace, a soaker tub, a covered porch, and a backyard, perfect for families or groups of up to 9 guests.

This charming 2-bedroom apartment is located in a historic district of Pittsfield, just a short walk from downtown, the lake, and local attractions. It consistently receives excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to 5 guests and features a spacious backyard, a fully equipped kitchen, and a finished attic that can be used as an extra sleeping area or a yoga space. Guests can enjoy modern amenities like air conditioning, a washer/dryer, and off-street parking for two cars, all within a beautifully preserved 1840s home.

This Hinsdale vacation home is conveniently located within 9 miles of Bas Ridge Golf Course, the Kushi Institute, and Canoe Meadows Wildlife Sanctuary, offering easy access to area attractions.
This three-bedroom, three-bathroom house sleeps up to 10 guests and includes in-house laundry, air conditioning, internet access, and is pet-friendly.

This Pittsfield house, situated on a quiet cul-de-sac near walking trails and a park with a playground, offers easy access to Lenox and Lee (15 minutes), Great Barrington (30 minutes), Mass MoCA, Mount Greylock State Reservation, The Clark Art Institute, and Jiminy Peak Ski Resort (30-45 minutes).
The remodeled two-story home features three bedrooms, two bathrooms, sleeps up to ten guests, includes a finished basement with a pull-out sofa and kids' play area, and provides a backyard with a BBQ and fire pit.

This Berkshire retreat in Richmond is a 3-bedroom, 2-bathroom apartment set on 2.5 acres, located 1 minute from Balderdash Cellars, 4 minutes from Hancock Shaker Village, and 9 minutes from Bousquet Mountain Ski Area.
This pet-friendly rental accommodates up to 6 guests and features a fully-equipped kitchen, outdoor grill, patio, high-speed Wi-Fi, air conditioning, and a fitness center, with professional housekeeping and daily local support.