Must See Cabin Suite Jiminy Sleeps 4- Mountainview
1 1
apartment , Hancock
This Hancock flat offers direct ski-in/ski-out access to Jiminy Peak Mountain, boasting stunning mountain views and keypad entry for convenient, keyless access. This well-appointed one-bedroom property accommodates up to four guests, featuring a kitchenette, air conditioning, and access to Jiminy Peak and Country Inn amenities including a year-round heated outdoor pool, hot tubs, and a fitness centre, all just 100 meters from the Adventure Park.
9.6 18 reviews
Pittsfield, MA
13/10 – 25/10
SG$388/nighttotal: SG$4656 (12 )
Lovely Ranch Home Getaway In The Berkshires- Just 6 Miles To Tanglewood
2 2
apartment , Richmond
This charming farmhouse is located just 10 kilometres from popular Berkshire attractions like Tanglewood, Kripalu, Shakespeare & Company, and the Norman Rockwell Museum, offering a peaceful escape in a rural setting. The property has received excellent reviews from previous guests, highlighting its comfort and amenities. This home has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a private deck with views, a large yard, a fire pit, a tree swing, a gas grill for outdoor dining, and a fully equipped kitchen.
This Hancock apartment building, situated near Jiminy Peak Mountain Resort (within 3.2km), offers ski-in/ski-out access and proximity to the Alpine Super Slide and Mountain Coaster (both within 3.2km), as well as Pittsfield State Forest and Taconic Ridge State Forest (both within 9.6km). This 46-square-metre self-catering flat features two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, indoor pool, fitness centre, hot tub, and parking.
9.5 4 reviews
Pittsfield, MA
30/06 – 31/10
SG$206/nighttotal: SG$25338 (123 )
Centrally Located, Charming 1bed
1 1
apartment , Pittsfield
This South Pittsfield apartment, a short drive (approx. 8km) from Lenox, 9.6km from Tanglewood, and 4km from Pittsfield city centre, offers easy access to Berkshire attractions. The self-catering property comprises a one-bedroom, one-bathroom unit sleeping two guests, featuring a dedicated workspace, extensive library, garden, fire pit, high-speed Wi-Fi, and smart TV.
10 2 reviews
Pittsfield, MA
13/10 – 18/10
SG$345/nighttotal: SG$1725 (5 )
Lake House Onota Lake
1 3
apartment , Pittsfield
This three-bedroom, two-bathroom lakeside house in Pittsfield, Massachusetts, is situated on Lake Onota, minutes from several ski areas and 24km from Tanglewood. The property sleeps eight guests and boasts direct lake access for swimming and boating, plus a kitchen, parking, and internet access; enjoy the peaceful lakeside setting and explore the Berkshires.
9.9 72 reviews
Pittsfield, MA
06/09 – 13/09
SG$449/nighttotal: SG$3143 (7 )
Spacious 4 Br+ House In The Heart Of Berkshires
5 2
apartment , Pittsfield
This five-bedroom, two-bathroom house in Pittsfield offers excellent wheelchair access via a wide wooden ramp and is conveniently located near hiking and skiing trails, and within easy driving distance of Tanglewood. Sleeping up to nine guests, the property boasts a well-equipped kitchen, a spacious garden, parking for four cars, and individual climate control in each of its rooms, including two with work areas and a separate office.
Pittsfield, MA
12/07 – 18/07
SG$255/nighttotal: SG$1530 (6 )
Mountain Lodge Getaway | Berkshires Charm
1 2
apartment , Pittsfield
This one-bedroom flat in Pittsfield is located in the scenic Berkshires, offering a mountain lodge retreat ideal for exploring the region's ski resorts, fall foliage, and summer outdoor activities. This apartment accommodates up to four guests and features internet, air conditioning, a kitchen, a swimming pool, a Jacuzzi, a fitness centre, and parking.
9.9 35 reviews
Pittsfield, MA
06/09 – 13/09
SG$613/nighttotal: SG$4291 (7 )
The Guest House At Cottage Farm
1 2
apartment , Pittsfield
This three-bedroom, three-bathroom holiday home, located on 12 private acres in Pittsfield, Massachusetts, is minutes from Tanglewood, Barrington Stage Company, Berkshire Theatre Group, Jacob's Pillow, MassMoCA, and the Norman Rockwell Museum. The 213-square-metre property boasts a fully remodelled kitchen, open-plan living space with exposed beams, and accommodates up to six guests, offering a private garden, parking, air conditioning, and internet access; a $20 insurance fee covers accidental damage.
9.7 46 reviews
Pittsfield, MA
06/09 – 13/09
SG$200/nighttotal: SG$1400 (7 )
Spacious Green 2 Bedroom Downtown
1 2
apartment , Pittsfield
This centrally located Pittsfield flat is a 0.8 km walk from local cafes, restaurants, and a cinema. The two-bedroom apartment, sleeping up to five guests, offers in-unit laundry, designated off-street parking, and a well-equipped kitchen including a fridge, microwave, and dishwasher.
10 12 reviews
Pittsfield, MA
03/07 – 06/07
SG$495/nighttotal: SG$1485 (3 )
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-ski On/off Country Inn Redone
1 2
apartment , Hancock
This Hancock slopeside apartment building is situated in the mountains, within 3km of Jiminy Peak Mountain Resort, offering ski-in/ski-out access and proximity to Pittsfield State Forest and Mount Greylock State Reservation (within 10km). This 46 square metre apartment features two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, indoor pool, fitness centre, hot tub, garden, and parking; enjoy nearby attractions such as the Alpine Super Slide and Mountain Coaster (within 3km).
Pittsfield, MA
30/06 – 31/10
SG$472/nighttotal: SG$58056 (123 )
Lenox/berkshire Charm
2 1
apartment , Lenox
This charming apartment is located on Main Street in Lenox, just a short walk from the town centre and a 5-kilometre drive from Tanglewood, offering easy access to restaurants, shops, and cultural attractions. The apartment has a private patio area and is suitable for up to four guests. Amenities include a full kitchen, laundry facilities, and a shared swimming pool, plus guests can enjoy nearby walking trails, kayaking, and skiing in the surrounding area.
9.6 34 reviews
Pittsfield, MA
03/07 – 06/07
SG$633/nighttotal: SG$1899 (3 )
Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous
2 2
apartment , Hancock
This apartment is located in Hancock, just a short walk from Jiminy Peak Mountain Resort and within easy reach of other attractions such as Zema's Nursery and Pittsfield State Forest. It has consistently received excellent reviews from previous guests. This two-bedroom, one-bathroom property spans 84 square metres and can comfortably accommodate up to eight guests. It features a fully equipped kitchen, a fireplace, a DVD player, and access to a swimming pool, jacuzzi, and fitness centre.
Best family friendly Pittsfield, MA Holiday Apartments and Self Catering Accommodations
Among the 130 accommodations in Pittsfield, MA, here are the 4 best family friendly holiday apartments
9.8 45 reviews
Pittsfield, MA
13/10 – 18/10
SG$392/nighttotal: SG$1960 (5 )
Berkshire Lakehouse - 3 Bedrooms - Sleeps 5
3 3
apartment , Pittsfield
This three-bedroom Pittsfield lakeside house, boasting excellent guest reviews, offers direct access to Onota Lake with a private dock and is conveniently located near Pittsfield's ski slopes and hiking trails, the precise distance unspecified. Sleeping up to five guests, this self-catering property features a fully equipped kitchen, a large deck with mountain views, a fenced yard, on-site laundry, and access to kayaks and paddleboards; a BBQ area is also available in the shared backyard.
9.7 40 reviews
Pittsfield, MA
06/09 – 13/09
SG$253/nighttotal: SG$1771 (7 )
Attractive Condo In The Berkshires.
1 2
apartment , Pittsfield
This apartment is located in a great neighbourhood in Pittsfield, just a short distance from the river and a canoe launch. It has consistently received excellent ratings for cleanliness, location and user experience. This charming three-bedroom property can accommodate up to six guests and offers a fully equipped kitchen, washer and dryer, a garage and storage space. Enjoy the convenience of a garden, air conditioning and internet access, as well as the unique charm of colonial lighting and tasteful design.
8.0 21 reviews
Pittsfield, MA
30/06 – 31/10
SG$207/nighttotal: SG$25461 (123 )
Wow-new Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk
1 1
apartment , Hancock
This Hancock apartment offers ski-in/ski-out access to Jiminy Peak, with Tanglewood and Cranwell Spa & Golf Club approximately 32 kilometres away. The 46-square-metre self-catering flat sleeps four, boasting a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, jacuzzi, and fitness centre.
10 3 reviews
Pittsfield, MA
13/10 – 25/10
SG$449/nighttotal: SG$5388 (12 )
Friendly Hills | Passive Home Ev Charger
3 2
apartment , Hancock
This Pittsfield holiday home, a short drive (under 5km) from Hancock Shaker Village and 3 minutes from Balderdash Cellars, offers convenient access to local attractions. The three-bedroom, two-bathroom apartment includes an attached garage, in-unit laundry, Wi-Fi, a fully equipped kitchen with oven, stovetop, refrigerator, microwave, coffee maker and toaster, and air conditioning; sleeps up to six guests comfortably.
Best Pittsfield, MA holiday apartments with a kitchen
10 33 reviews
Pittsfield, MA
13/10 – 25/10
SG$338/nighttotal: SG$4056 (12 )
Lenox Retreat Near Tanglewood W/ Rescued Donkeys
1 2
apartment , Lenox
This Lenox apartment, a renovated 1770s stagecoach stop, is situated near Tanglewood and various Berkshire attractions. The two-bedroom property sleeps five, offering a kitchenette, garden access, parking, and the unique opportunity to visit mini donkeys (booking required), within a spacious, family-friendly setting.
10 5 reviews
Pittsfield, MA
06/09 – 13/09
SG$254/nighttotal: SG$1778 (7 )
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!
2 2
apartment , Pittsfield
This charming bungalow is situated in the city centre of Pittsfield, just 5km from Bousquet Ski Resort, 20km from Jiminy Peak and 15km from Tanglewood in Lenox, offering easy access to the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests. The home sleeps up to 5 guests and spans 93 square metres. It features a fully equipped kitchen, a spa, air conditioning and a private deck with a grill, perfect for enjoying the outdoors.
9.8 7 reviews
Pittsfield, MA
03/07 – 06/07
SG$377/nighttotal: SG$1131 (3 )
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
1 2
apartment , Hancock
This Hancock apartment is conveniently located just 0.1 miles from Jiminy Peak Mountain Resort and within 9 miles of several attractions including Zema's Nursery, Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, and Brodie Mountain. The property has received excellent user ratings. The apartment has one bedroom and one bathroom, comfortably accommodating up to five guests. It offers a fully equipped kitchen, a terrace, a garden, a swimming pool, a fitness centre and parking, along with amenities like internet access, air conditioning, and a TV.
Pittsfield, MA
21/08 – 24/08
SG$929/nighttotal: SG$2787 (3 )
New Built - Split Level House In The Berkshires
1 6
apartment , Lanesborough
This newly built Lanesborough residence is situated on a quiet street, a mere 300 metres from Pontoosuc Lake, and a short drive to Jiminy Peak for skiing, the Ashuwillticook Rail Trail for cycling, and Pittsfield State Park for its natural beauty. This spacious three-bedroom, three-bathroom house accommodates up to eight guests and includes amenities such as air conditioning, Wi-Fi, a kitchen, and parking for four vehicles, with outdoor EV charging available.
Frequently asked questions about apartment rentals in Pittsfield, MA
What are the must-see attractions for a 2 days stay in Pittsfield, MA?
For a two-day trip, you should definitely visit the Berkshire Museum, which has exhibits on art, science and natural history. Also, don't miss the Clark Art Institute, which has a collection of Impressionist and Post-Impressionist paintings. And if you're interested in theatre, the Barrington Stage Company puts on a great season of plays.
Which neighborhoods in Pittsfield, MA are best for renting an apartment?
The best neighbourhoods for renting an apartment are the ones near the downtown area. They're within walking distance of shops, restaurants and the Berkshire Museum. The area around the Berkshire Mall is also good, as it has a lot of amenities. If you're looking for something quieter, the area around the Clark Art Institute is a good option.
What are the best apartments with a pool in Pittsfield, MA?
What are the top cultural and historical sites in Pittsfield, MA?
Pittsfield is known for its cultural and historical sites. The Berkshire Museum is a great place to learn about the area's history and art. The Clark Art Institute is another must-see, and its collection of Impressionist and Post-Impressionist paintings is world-renowned. The Colonial Theatre is a beautiful historic theatre that hosts a variety of performances.
What are the best apartments with a jacuzzi in Pittsfield, MA?
Pittsfield is known for its beautiful scenery and its vibrant arts and culture scene. It's also home to the Clark Art Institute, which has a world-renowned collection of Impressionist and Post-Impressionist paintings. And the city has a rich history, with many historic buildings and landmarks.
What are the best apartments for families and kids in Pittsfield, MA?
Where can you find the best local markets and street food in Pittsfield, MA?
Pittsfield has a great farmers' market on Saturdays in the summer, where you can find fresh produce, baked goods and local crafts. The city also has a few food trucks that park in different locations throughout the week. And if you're looking for a quick bite, there are plenty of cafes and restaurants in the downtown area.
What are the best pet friendly apartments in Pittsfield, MA?
How is the public transportation system in Pittsfield, MA?
Pittsfield has a public transportation system that includes buses. The system is not as extensive as in larger cities, but it can get you around the city and to nearby towns. The Berkshire Regional Transit Authority operates the buses.
What are the best apartments with parking in Pittsfield, MA?
Which seasonal events or festivals should apartment renters look forward to in Pittsfield, MA?
Pittsfield has a lot of great seasonal events, including the Pittsfield Farmers Market, the Berkshire Arts & Crafts Fair, and the First Night Pittsfield celebration. The city also hosts a number of music festivals throughout the year.
What amenities are typically included in apartments in Pittsfield, MA?
Apartments in Pittsfield typically include basic amenities like central heating and air conditioning, a refrigerator, stove and oven. Some apartments may also have a dishwasher, washer and dryer, and a balcony or patio. You can find apartments with a range of features, from basic to luxurious, depending on your budget.
Destinations nearby
Best Pittsfield, MA holiday apartments with air conditioning
10 6 reviews
Pittsfield, MA
06/09 – 13/09
SG$252/nighttotal: SG$1764 (7 )
Quiet Studio In Desirable Neighborhood
1 2
apartment , Pittsfield
This Pittsfield studio apartment is centrally located in the city's Historic District, a short 4.8-kilometre drive from Berkshire Medical Center and 5.6 kilometres from General Dynamics Mission Systems. The self-contained apartment, sleeping up to two guests, offers a kitchen with dishwasher, air conditioning, a shared laundry, and access to a swimming pool and garden; plus it's within walking distance of restaurants, theatres, shops and museums.
9.9 114 reviews
Pittsfield, MA
13/10 – 18/10
SG$342/nighttotal: SG$1710 (5 )
Marie's Place, Unit 1
3 3
apartment , Pittsfield
This apartment is conveniently located in downtown Pittsfield, just 7km from the Bosquet ski area and 28km from Jiminy Peak, making it ideal for exploring the town and enjoying winter sports. The property has received excellent ratings for cleanliness, location, and user experience. The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and a wet towel basket in each bedroom, ensuring a comfortable stay.
Pittsfield, MA
13/10 – 18/10
SG$382/nighttotal: SG$1910 (5 )
Cozy Cottage In The Berkshires
1 3
apartment , Pittsfield
This one-bedroom flat in Pittsfield is conveniently situated, a mere 3-minute drive from both the Colonial Theatre and the Berkshire Museum, placing you in prime position to explore the town and the wider Berkshire region. This comfortable flat accommodates up to four guests and includes essential amenities such as air conditioning, on-site laundry facilities with a washing machine and dryer, and provided linens and towels for a convenient stay.
9.8 21 reviews
Pittsfield, MA
03/07 – 06/07
SG$496/nighttotal: SG$1488 (3 )
Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
1 2
apartment , Hancock
This apartment is situated in Hancock, just 0.16km from Jiminy Peak Mountain Resort and within 14.5km of Zema's Nursery, Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, and Brodie Mountain. This property has received excellent user ratings, making it a popular choice for travellers. This one-bedroom apartment is 46 square metres in size and can comfortably accommodate up to four guests. The apartment offers a range of amenities and features, including a fully equipped kitchen, a fireplace, a DVD player and TV, a sofa bed, a swimming pool, a jacuzzi, and parking.
Best pet-friendly Pittsfield, MA holiday apartments
Among the 130 accommodations in Pittsfield, MA, here are the 4 best pet friendly holiday apartments
9.8 101 reviews
Pittsfield, MA
13/10 – 18/10
SG$507/nighttotal: SG$2535 (5 )
Berkshire Getaway Ranch 3 Acres + Saltwater Pool
2 3
apartment , Pittsfield
This two-bedroom apartment is situated in the Berkshires, just a short drive (under 8km) from Pittsfield, with easy access to Onota and Pontoosuc lakes, as well as popular ski resorts. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment offers a spacious layout, accommodating up to 7 guests, with multiple living areas, including a sun room and a secondary living room with a wet bar. Guests can enjoy a range of amenities, including a private saltwater pool, a well-equipped kitchen, a fitness centre, and a two-car garage.
9.9 67 reviews
Pittsfield, MA
13/10 – 18/10
SG$305/nighttotal: SG$1525 (5 )
Modern Gem In The Heart Of Berkshires
1 3
apartment , Pittsfield
This two-bedroom apartment is conveniently located in Pittsfield, just 10 kilometres from Bousquet Ski Resort and 15 kilometres from Jiminy Peak. The apartment has received excellent ratings for location, cleanliness, and overall user experience. The apartment is suitable for up to four guests and features a spacious living and dining area, a well-equipped kitchen, a screened-in porch, and a shared backyard. Guests can enjoy amenities such as air conditioning, internet access, a washing machine and dryer, and a modern bathroom with a double vanity.
9.7 21 reviews
Pittsfield, MA
13/10 – 18/10
SG$573/nighttotal: SG$2865 (5 )
Spacious Historic Home In The Berkshires!
5 3
apartment , Pittsfield
This five-bedroom holiday home is situated just a short distance from Pittsfield town centre, offering easy access to restaurants, shops and cultural attractions, and is only 11 kilometres from Tanglewood. The pet-friendly property features a fully equipped kitchen, a fireplace, a soaker tub, a covered porch, a barbecue and a garden, making it ideal for families or groups of up to nine people.
Pittsfield, MA
30/06 – 31/10
SG$406/nighttotal: SG$49938 (123 )
Beautiful Renovated Home, Close To Multiple Ski Mountains.
3 1
apartment , Hinsdale
This Hinsdale holiday home is conveniently located within 14.5 kilometres of Bas Ridge Golf Course, the Kushi Institute, and Canoe Meadows Wildlife Sanctuary. The three-bedroom, three-bathroom property sleeps up to ten guests and includes in-house laundry facilities, ensuring a comfortable stay with easy access to local amenities and attractions.
