Berkshire Getaway Ranch 3 Acres + Saltwater Pool
apartment, Pittsfield
This Pittsfield apartment is located in a peaceful rural setting in the Berkshires, just minutes from lakes, ski resorts, and charming towns like Lenox, Williamstown, and North Adams. The apartment has excellent user, location, and cleanliness ratings. The 2-bedroom, 2-bathroom home offers spacious living areas for up to 7 guests. Enjoy amenities including a saltwater pool, fitness center, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful Berkshire scenery.
Beautiful Blue Studio Downtown 5 Mins To Downtown
apartment, Pittsfield
This Pittsfield studio apartment boasts a convenient downtown location, a 5-minute walk from numerous amenities including cafes, shops, restaurants, and a movie theater.
The self-contained unit sleeps two guests and features a kitchen, air conditioning, parking, and excellent internet access; explore Pittsfield's attractions from this ideal base.
The self-contained unit sleeps two guests and features a kitchen, air conditioning, parking, and excellent internet access; explore Pittsfield's attractions from this ideal base.
2 Bed Berkshire Apt Minutes To Jiminy Peak Ski
apartment, East Nassau
This Hancock apartment rental is located near Jiminy Peak Ski Resort, approximately 21 miles from Tanglewood and other Berkshire attractions.
The 1000-square-foot unit features two bedrooms, one bathroom, and accommodates up to six guests, offering a fully equipped kitchen, free Wi-Fi, private parking, air conditioning, an outdoor fireplace, garden, and outdoor play equipment.
The 1000-square-foot unit features two bedrooms, one bathroom, and accommodates up to six guests, offering a fully equipped kitchen, free Wi-Fi, private parking, air conditioning, an outdoor fireplace, garden, and outdoor play equipment.
Pine & Paddle | Pond Access Kayaks
cottage, Richmond
This 2-bedroom, 1-bathroom apartment in Richmond provides a country cottage experience with a private community beach on Richmond Pond, a short walk away, and is near Tanglewood and Bousquet.
This pet-friendly unit accommodates up to 4 guests and features a newly renovated kitchen with a convection oven and induction cooktop, a wood-burning fireplace, a balcony for dining, and access to local attractions like apple picking and hiking trails.
This pet-friendly unit accommodates up to 4 guests and features a newly renovated kitchen with a convection oven and induction cooktop, a wood-burning fireplace, a balcony for dining, and access to local attractions like apple picking and hiking trails.
Condo ∙ 2 Bedrooms ∙ 6 Guests
apartment, Lenox
This Lenox, Massachusetts condo rental is conveniently located in the Berkshires, a short drive from The Mount (2.9 miles), Norman Rockwell Museum (7.2 miles), and Tanglewood (4.3 miles).
This two-bedroom, three-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, private deck with scenic pond views, access to resort amenities including indoor/outdoor pools, a fitness center, and a sauna.
This two-bedroom, three-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, private deck with scenic pond views, access to resort amenities including indoor/outdoor pools, a fitness center, and a sauna.
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4
apartment, Hancock
This Hancock apartment, the "Game Night Suite at Jiminy Peak," is conveniently located near Jiminy Peak Ski Resort and 34 miles from Albany International Airport.
The 500-square-foot unit features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, and fitness center.
The 500-square-foot unit features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, and fitness center.
Cozy Pittsfield Gem W/ Deck, Gazebo & Fireplace!
apartment, Pittsfield
This 3-bedroom, 3-bathroom Pittsfield apartment offers convenient access to outdoor recreation, located 8 miles from Bousquet Mountain Ski Area and 12 miles from Jiminy Peak Mountain Resort, with Ashuwillticook Rail Trail just 1 mile away and Pittsfield State Forest 8 miles distant.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
Modern Gem In The Heart Of Berkshires
apartment, Pittsfield
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.
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.
Lakeside Estate 2 Homes For Family Gatherings
house, Lenox
This Lenox vacation home is located 1.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewood Musical Center, offering convenient access to local attractions.
This air-conditioned rental accommodates up to 18 guests with 1 bedroom and 5 bathrooms, featuring complimentary WiFi, a full kitchen, a garden, and private parking.
This air-conditioned rental accommodates up to 18 guests with 1 bedroom and 5 bathrooms, featuring complimentary WiFi, a full kitchen, a garden, and private parking.
Lake House Onota Lake
apartment, Pittsfield
This three-bedroom, two-bathroom lakeside house on Lake Onota in Pittsfield, Massachusetts, is minutes from several ski areas and a 15-minute drive from Tanglewood.
The 8-guest home offers direct lake access for swimming and boating, a fully equipped kitchen, parking, internet, and proximity to numerous outdoor recreational opportunities.
The 8-guest home offers direct lake access for swimming and boating, a fully equipped kitchen, parking, internet, and proximity to numerous outdoor recreational opportunities.
Comfortable Charming Home In The Town Of Dalton
apartment, Dalton
This recently renovated 2-bedroom, 1-bathroom apartment in Dalton offers accessible features, a south-facing living room, and a semi-private backyard, providing a comfortable and convenient stay for up to four guests. Enjoy the ease of an open-concept layout, in-unit laundry, and ample parking for three vehicles, all within a peaceful residential area of Dalton.
The Reel Retreat | Theatre & Firepit Game Room
apartment, Pittsfield
This four-bedroom, two-bathroom Pittsfield vacation rental is located in southern Pittsfield, minutes from downtown Pittsfield and Lenox, providing easy access to Tanglewood and Barrington Stage Company.
The 4-bedroom home boasts a private backyard, a fully equipped kitchen, a dedicated movie theater, a game room, and a deck with a grill, comfortably accommodating up to 7 guests and offering proximity to Bousquet Ski Area, Canoe Meadows, and Kennedy Park.
The 4-bedroom home boasts a private backyard, a fully equipped kitchen, a dedicated movie theater, a game room, and a deck with a grill, comfortably accommodating up to 7 guests and offering proximity to Bousquet Ski Area, Canoe Meadows, and Kennedy Park.
