Pittsfield, MA
06/30 – 10/31
$161/nighttotal: $19803 (123 )
Must See Cabin Suite Jiminy Sleeps 4- Mountainview
1 1apartment , Hancock
This Hancock, Massachusetts condo is located directly on Jiminy Peak Mountain, providing ski-in/ski-out access in winter and immediate access to hiking trails in summer, plus proximity to Jiminy Peak Mountain Resort's Adventure Park.
The fully renovated one-bedroom suite sleeps four with a king bed, queen sofa bed, kitchenette (including a Keurig), two TVs, and access to Jiminy Peak's year-round heated pool, hot tubs, and fitness center.
The fully renovated one-bedroom suite sleeps four with a king bed, queen sofa bed, kitchenette (including a Keurig), two TVs, and access to Jiminy Peak's year-round heated pool, hot tubs, and fitness center.
Pittsfield, MA
07/03 – 07/06
$595/nighttotal: $1785 (3 )
Home In The Berkshires
4 2apartment , Hancock
This 4-bedroom, 3-bathroom apartment in Williamstown, Berkshire County, is located 5 minutes from Jiminy Peak Mountain Resort and 10 minutes from the Ashuwillticook rail trail, offering a secluded 3-acre property with hiking opportunities.
This 2000 square foot vacation home comfortably sleeps 8 guests, featuring two master suites, a kitchen with a fridge and dishwasher, a TV/playroom, and outdoor space with a terrace/balcony and garden, while being conveniently close to various Berkshires attractions.
This 2000 square foot vacation home comfortably sleeps 8 guests, featuring two master suites, a kitchen with a fridge and dishwasher, a TV/playroom, and outdoor space with a terrace/balcony and garden, while being conveniently close to various Berkshires attractions.
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
06/30 – 10/31
$171/nighttotal: $21033 (123 )
Deluxe Mountain View Nautical Suite Jiminy Ski On/
1 1apartment , Hancock
This Hancock, Massachusetts apartment rental, located at the Country Inn and High Seas directly on Jiminy Peak Mountain, offers ski-in/ski-out access in winter and easy access to the Jiminy Peak Mountain Resort's summer activities.
The newly renovated one-bedroom unit sleeps four with a king bed, queen sofa bed, fully equipped kitchenette including an air fryer, and in-suite amenities such as smart TVs and board games; guests enjoy resort amenities like a heated pool, hot tubs, and a fitness center.
The newly renovated one-bedroom unit sleeps four with a king bed, queen sofa bed, fully equipped kitchenette including an air fryer, and in-suite amenities such as smart TVs and board games; guests enjoy resort amenities like a heated pool, hot tubs, and a fitness center.
Pittsfield, MA
06/30 – 10/31
$129/nighttotal: $15867 (123 )
Entire Home In Dalton, Massachusetts, United States
1 1cottage , Dalton
This Dalton, Massachusetts cottage is located 0.9 miles from the Crane Museum of Papermaking and within 6 miles of Wahconah Falls State Park, Bas Ridge Golf Course, and the Barrington Stage Company.
This one-bedroom, one-bathroom house sleeps four and includes a washer, hairdryer, iron, and ironing board; nearby activities include golfing and exploring the Crane Museum.
This one-bedroom, one-bathroom house sleeps four and includes a washer, hairdryer, iron, and ironing board; nearby activities include golfing and exploring the Crane Museum.
Pittsfield, MA
06/30 – 10/31
$422/nighttotal: $51906 (123 )
Grandparents Cottage 250 Steps To The Lake
4 1cottage , Stockbridge
This West Stockbridge rental is ideally situated near Tanglewood (6 minutes), the Berkshire Botanical Garden (7 minutes), and the Housatonic River (8 minutes), offering easy access to Stockbridge's cultural and natural attractions.
This four-bedroom, two-bathroom house sleeps seven and includes Wi-Fi, a dryer, and essential amenities; nearby attractions include Guido's Marketplace and Lee Premium Outlets.
This four-bedroom, two-bathroom house sleeps seven and includes Wi-Fi, a dryer, and essential amenities; nearby attractions include Guido's Marketplace and Lee Premium Outlets.
Pittsfield, MA
10/13 – 10/18
$379/nighttotal: $1895 (5 )
Berkshire Getaway Ranch 3 Acres + Saltwater Pool
2 3apartment , 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.
Pittsfield, MA
07/03 – 07/06
$804/nighttotal: $2412 (3 )
Ski's The Day: Winsome 3-bedroom Mountain Townhome With Ac In Jiminy Peak
3 2apartment , Hancock
This 3-bedroom townhome at Jiminy Peak resort in Hancock offers prime walking access to ski slopes, tennis courts, dining, and three swimming pools, with Mount Lebanon Shaker Village and the Colonial Theater nearby.
This accommodation provides a well-appointed kitchen, a king-size pit-sofa with a fireplace, a furnished deck, and infant amenities, accommodating up to 8 guests with on-site attractions like the Mountain Coaster and Alpine Super Slide.
This accommodation provides a well-appointed kitchen, a king-size pit-sofa with a fireplace, a furnished deck, and infant amenities, accommodating up to 8 guests with on-site attractions like the Mountain Coaster and Alpine Super Slide.
Pittsfield, MA
06/30 – 10/31
$181/nighttotal: $22263 (123 )
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-ski On/off Country Inn Redone
1 1apartment , Hancock
This Hancock slopeside condo is located within two miles of Jiminy Peak Mountain Resort, offering convenient access to skiing, the Alpine Super Slide, and the Mountain Coaster.
This 500-square-foot unit features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, an indoor pool, hot tub, and fitness center.
This 500-square-foot unit features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, an indoor pool, hot tub, and fitness center.
Pittsfield, MA
10/13 – 10/18
$370/nighttotal: $1850 (5 )
Lake/mountain View Getaway
1 3apartment , Pittsfield
This Pittsfield home, ideally located near Pontoosuc Lake, offers stunning views of the lake and Mount Greylock, with easy walking access to a public beach and boat rentals.
The two-bedroom, two-bathroom house sleeps seven guests comfortably, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a spacious living room, and a variety of sleeping arrangements including a king bed, twin-over-full bunk bed, and queen sofa bed, perfect for families or groups visiting the Berkshires.
The two-bedroom, two-bathroom house sleeps seven guests comfortably, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a spacious living room, and a variety of sleeping arrangements including a king bed, twin-over-full bunk bed, and queen sofa bed, perfect for families or groups visiting the Berkshires.
Pittsfield, MA
07/03 – 07/06
$835/nighttotal: $2505 (3 )
Comfortable Berkshires Retreat On Mtn Resort, Siso
4 2resort , Hancock
The Comfortable Berkshires Retreat On Mtn Resort, Siso in Hancock, Massachusetts is located 0.6 miles from Jiminy Peak Mountain Resort and within 3 miles of the Alpine Super Slide and Mountain Coaster.
This 12-bedroom, 3-bathroom vacation home offers guests a fitness center, sauna, hot tub, and a fully equipped kitchen, accommodating up to 12 people and featuring family-friendly amenities like an arcade/game room and a garden.
This 12-bedroom, 3-bathroom vacation home offers guests a fitness center, sauna, hot tub, and a fully equipped kitchen, accommodating up to 12 people and featuring family-friendly amenities like an arcade/game room and a garden.
Pittsfield, MA
07/12 – 07/18
$691/nighttotal: $4146 (6 )
Berkshires Chalet Mins To Tanglewood/lenox
4 2apartment , Richmond
This Richmond rental is located approximately 4 miles from Tanglewood and offers convenient access to Berkshire attractions, including skiing, swimming, boating, hiking, summer theater, and dining. This 4-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a new kitchen with stainless steel appliances, a screened porch, central air conditioning, and a covered outdoor hot tub.
