Pittsfield, MA
10/13 – 10/18
$407/nighttotal: $2035 (5 )
Spacious 4 Br+ House In The Heart Of Berkshires
5 3apartment , Pittsfield
This five-bedroom, two-bathroom Pittsfield home offers easy access to hiking and skiing trails, and a short drive to Tanglewood.
The spacious residence, perfect for families or groups up to nine, boasts a fully equipped kitchen, ample parking, a well-maintained yard, and wheelchair accessibility via a ramp; nearby activities include exploring the Berkshires.
The spacious residence, perfect for families or groups up to nine, boasts a fully equipped kitchen, ample parking, a well-maintained yard, and wheelchair accessibility via a ramp; nearby activities include exploring the Berkshires.
Pittsfield, MA
09/06 – 09/13
$450/nighttotal: $3150 (7 )
Spacious Historic Home In The Berkshires!
5 2apartment , Pittsfield
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 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.
Pittsfield, MA
09/06 – 09/13
$279/nighttotal: $1953 (7 )
Beautiful & Serene Getaway
1 2apartment , Pittsfield
This three-bedroom, one-bathroom Pittsfield apartment rental is located in a quiet neighborhood minutes from downtown, offering easy access to shops, restaurants, and a short drive to Tanglewood and Mass MoCA.
The 3-bedroom unit features a spacious kitchen, large living area, in-unit laundry, enclosed backyard with porch and grill, accommodating up to 7 guests and providing a tranquil escape near numerous parks and walking trails.
The 3-bedroom unit features a spacious kitchen, large living area, in-unit laundry, enclosed backyard with porch and grill, accommodating up to 7 guests and providing a tranquil escape near numerous parks and walking trails.
Pittsfield, MA
07/03 – 07/06
$492/nighttotal: $1476 (3 )
Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous
2 2apartment , Hancock
This Hancock apartment offers ski-in/ski-out access and is 0.1 miles from Jiminy Peak Mountain Resort. It's within 9 miles of Zema's Nursery, Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, and Brodie Mountain. It has an excellent user rating.
The apartment has two bedrooms, one bathroom, and a sofa bed. It can accommodate up to 8 guests and has a floor area of 900 square feet. It features a kitchen with a refrigerator and oven, a fireplace, a DVD player, and air conditioning. Guests have access to a fitness center, a swimming pool, a Jacuzzi, and parking.
The apartment has two bedrooms, one bathroom, and a sofa bed. It can accommodate up to 8 guests and has a floor area of 900 square feet. It features a kitchen with a refrigerator and oven, a fireplace, a DVD player, and air conditioning. Guests have access to a fitness center, a swimming pool, a Jacuzzi, and parking.
Pittsfield, MA
07/01 – 07/31
$460/nighttotal: $13800 (30 )
Mountainside: Large 3-level Jiminy Peak Home
1 1apartment , Hancock
This spacious three-level Hancock condo, near Jiminy Peak Mountain Resort and a short drive from Williamstown and Pittsfield, offers easy access to skiing, hiking, and area attractions.
The 1850-square-foot property boasts four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, swimming pool, jacuzzi, fitness center, and dedicated parking, plus family-friendly features like a game nook and play area.
The 1850-square-foot property boasts four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, swimming pool, jacuzzi, fitness center, and dedicated parking, plus family-friendly features like a game nook and play area.
Pittsfield, MA
09/06 – 09/13
$277/nighttotal: $1939 (7 )
Cantabile Life In The Berkshires
1 2apartment , Pittsfield
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.
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.
Pittsfield, MA
09/06 – 09/13
$393/nighttotal: $2751 (7 )
Berkshire's Sweet Spot 2-pool And Spa
3 2apartment , Pittsfield
This Pittsfield duplex is conveniently located in central Berkshire County, within walking distance of downtown Pittsfield, Tanglewood, and the Mahaiwe Performing Arts Center. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The home features three bedrooms and a queen-sized sofa bed, comfortably sleeping up to eight guests. Enjoy a private backyard with a seasonal pool, a year-round hot tub, a fully equipped kitchen, and modern amenities like smart TVs.
The home features three bedrooms and a queen-sized sofa bed, comfortably sleeping up to eight guests. Enjoy a private backyard with a seasonal pool, a year-round hot tub, a fully equipped kitchen, and modern amenities like smart TVs.
Pittsfield, MA
10/13 – 10/18
$243/nighttotal: $1215 (5 )
Cozy Bungalow In Se Pittsfield
1 3apartment , Pittsfield
This Pittsfield apartment is located just 5 minutes from Bousquet Ski Mountain and 20 minutes from Jiminy Peak, offering easy access to outdoor activities in the Berkshires. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The rental is a single-floor home with space for 5 guests. It features a fully equipped kitchen, a private garden, a deck and an enclosed porch, and a grill for cookouts, making it ideal for entertaining friends and family.
The rental is a single-floor home with space for 5 guests. It features a fully equipped kitchen, a private garden, a deck and an enclosed porch, and a grill for cookouts, making it ideal for entertaining friends and family.
Pittsfield, MA
07/03 – 07/06
$373/nighttotal: $1119 (3 )
Escape To The Heart Of Jiminy Peak: Country Inn Condo With Full Kitchen, 2 Bths
1 2apartment , Hancock
This ski-in/ski-out condo at Jiminy Peak Resort in Hancock, Massachusetts offers direct access to 45 slopes.
The spacious one-bedroom unit features two bathrooms, a fully equipped kitchen with microwave and dishwasher, and accommodates up to four guests, boasting resort amenities including a pool, jacuzzi, and fitness center.
The spacious one-bedroom unit features two bathrooms, a fully equipped kitchen with microwave and dishwasher, and accommodates up to four guests, boasting resort amenities including a pool, jacuzzi, and fitness center.
Pittsfield, MA
07/03 – 07/06
$488/nighttotal: $1464 (3 )
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
1 2apartment , Hancock
This Hancock condo is located in the Village Center of Jiminy Peak Mountain Resort, directly across from the main ski lift, providing ski-in/ski-out access.
The 650-square-foot unit sleeps four, features a fully equipped kitchen with a Keurig and air fryer, and offers access to a year-round heated pool, hot tubs, and a fitness center.
The 650-square-foot unit sleeps four, features a fully equipped kitchen with a Keurig and air fryer, and offers access to a year-round heated pool, hot tubs, and a fitness center.
Pittsfield, MA
07/01 – 07/31
$51/nighttotal: $1530 (30 )
Your Glamping Getaway
1 1glamping , East Nassau
This refurbished RV glamping site is located on a 75-acre property in East Nassau, offering a rural retreat with access to local natural beauty.
Accommodating up to 4 guests, this glamping experience features a full gas range oven, refrigerator, toilet with shower, a cold spring-fed pool, and a gas grill, all set within expansive grounds perfect for nature observation.
Accommodating up to 4 guests, this glamping experience features a full gas range oven, refrigerator, toilet with shower, a cold spring-fed pool, and a gas grill, all set within expansive grounds perfect for nature observation.
Pittsfield, MA
09/06 – 09/13
$277/nighttotal: $1939 (7 )
Bb's Central Berkshire Home
1 2apartment , Pittsfield
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.
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.
