Pittsfield, MA
1 1
$425/nighttotal: $11900 (28 )
The Oliver Wendell Holmes Guesthouse @ Holmesdale
apartment - Pittsfield
Historic Holmesdale Cottage is situated on 16 acres of a private estate on the Pittsfield/Lenox border, offering tranquility amidst the Berkshires. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom cottage accommodates up to four guests, featuring a king-size bed and a spiral staircase.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.
Pittsfield, MA
2 5
$269/nighttotal: $1345 (5 )
Spacious Historic Home In The Berkshires!
apartment - Pittsfield
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 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.
Pittsfield, MA
2 2
$246/nighttotal: $1476 (6 )
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.
Pittsfield, MA
2 2
$194/nighttotal: $1164 (6 )
Downtown Apartment A
apartment - Pittsfield
This Pittsfield apartment is conveniently located in a quiet neighborhood, just 5 minutes from Bousquet Ski Area and close to Jimmy Peak, making it ideal for winter sports enthusiasts. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.
Pittsfield, MA
2 3
$256/nighttotal: $1280 (5 )
Bb's Central Berkshire Home
apartment - 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.
Pittsfield, MA
1 1
$139/nighttotal: $834 (6 )
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.
Pittsfield, MA
1 2
$134/nighttotal: $804 (6 )
Hawksnest: Quiet 2br Apt, Heart Of The Berkshires
apartment - Pittsfield
This renovated Pittsfield apartment, conveniently located off Highway 7, provides easy access to Berkshire attractions like Kripalu Center for Yoga & Health, Lenox, and Tanglewood (all within 15 minutes).
The 2-bedroom, 1-bathroom rental offers a private entrance, a screened porch, shared backyard access, and accommodates up to 4 guests with amenities including air conditioning, free internet, and parking.
The 2-bedroom, 1-bathroom rental offers a private entrance, a screened porch, shared backyard access, and accommodates up to 4 guests with amenities including air conditioning, free internet, and parking.
Pittsfield, MA
2 1
$138/nighttotal: $828 (6 )
Mountain Getaway Suite Ski Onoff Jiminy Peak - Fully Redone Decor
apartment - Hancock
This Hancock condo offers ski-on/ski-off access to Jiminy Peak with mountain views, located 19 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center.
This 500 square feet suite accommodates up to 7 guests, featuring a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, a swimming pool, and a fitness center.
This 500 square feet suite accommodates up to 7 guests, featuring a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, a swimming pool, and a fitness center.
Pittsfield, MA
2 1
$138/nighttotal: $828 (6 )
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.
Pittsfield, MA
1 2
$269/nighttotal: $1614 (6 )
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!
apartment - Pittsfield
This centrally located bungalow in Pittsfield is just minutes away from popular attractions such as Bousquet Ski Resort, hiking trails, museums, and Tanglewood in Lenox. It offers easy access to urban amenities, and has been rated as "excellent" by previous guests.
The bungalow has a floor area of 1000 square feet and can accommodate up to 5 guests. It has 2 bedrooms, 1 bathroom, a kitchen with a fridge, microwave oven, and dishwasher, and air conditioning. The bungalow also features a spa, an outdoor deck, a yard with games and a grill, and convenient access to hiking trails and museums.
The bungalow has a floor area of 1000 square feet and can accommodate up to 5 guests. It has 2 bedrooms, 1 bathroom, a kitchen with a fridge, microwave oven, and dishwasher, and air conditioning. The bungalow also features a spa, an outdoor deck, a yard with games and a grill, and convenient access to hiking trails and museums.
Pittsfield, MA
1 5
$450/nighttotal: $2700 (6 )
Spacious 4 Br+ House In The Heart Of Berkshires
apartment - 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
2 3
$209/nighttotal: $1254 (6 )
Dancing Horse Lodge
apartment - Pittsfield
This vacation rental is located in the mountains, just a short drive from Pittsfield's cultural attractions like the Colonial Theater, Berkshire Museum, and Housatonic River. The house has earned excellent ratings for its cleanliness, location, and overall experience.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
