Compare Vacation Rentals & Airbnb in Pittsfield, MA
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157 Rentals and Airbnb in Pittsfield, MA
9.5 4 reviews
Pittsfield, MA
03/07 – 06/07
$321/nighttotal: $963 (3 )
Huttopia Berkshires
1 2
glamping , Hancock
Huttopia Berkshires, in the Berkshires region of Massachusetts, is located 36km from Cranwell Spa & Golf Resort, 41km from Tanglewood Music Center and Tanglewood Park, and 57km from Albany International Airport. This one-bedroom, one-bathroom glamping unit at Huttopia Berkshires offers a kitchenette, terrace, and access to an on-site restaurant, swimming pool, and garden; pets are welcome.
9.5 4 reviews
Pittsfield, MA
30/06 – 31/10
$224/nighttotal: $27552 (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.
9.6 34 reviews
Pittsfield, MA
03/07 – 06/07
$688/nighttotal: $2064 (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.
9.2 78 reviews
Pittsfield, MA
13/10 – 18/10
$235/nighttotal: $1175 (5 )
Charming Beautiful Apartment In Central Pittsfield
1 3
apartment , Pittsfield
This two-bedroom apartment in Pittsfield is located just 2 kilometres from the town centre and 3 kilometres from the lake, offering easy access to both the vibrant town and the tranquil lakeside. The apartment has received excellent ratings for its cleanliness, location, and overall experience. The property offers a spacious living space suitable for up to 5 guests. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a private garden, off-street parking, and a washer and dryer.
9.9 93 reviews
Pittsfield, MA
13/10 – 18/10
$518/nighttotal: $2590 (5 )
Lake/mountain View Getaway
1 3
apartment , Pittsfield
This Pittsfield house, boasting spectacular views of Pontoosuc Lake and Mount Greylock, is a short walk from a public beach and boat rentals. Sleeping up to seven guests, this two-bedroom, two-bathroom property features a fully equipped kitchen with dishwasher, parking, and a spacious living room; nearby attractions include Berkshire ski mountains.
Pittsfield, MA
30/06 – 31/10
$513/nighttotal: $63099 (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.
9.8 8 reviews
Pittsfield, MA
30/06 – 31/10
$239/nighttotal: $29397 (123 )
1st Floor Mountain View Suite Ski On/off At Jiminy
1 1
apartment , Hancock
This ground-floor apartment at Jiminy Peak Mountain Resort in Hancock, Massachusetts offers ski-in/ski-out access in winter and proximity to summer activities. The one-bedroom, one-bathroom flat sleeps four guests, featuring a king bed, queen sofa bed, fully equipped kitchenette with appliances including a dishwasher and air fryer, plus a private coded lock, smart TVs, and access to resort amenities such as a heated pool and fitness centre.
Pittsfield, MA
06/09 – 13/09
$331/nighttotal: $2317 (7 )
Cozy Cottage In The Berkshires
1 2
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.
Pittsfield, MA
30/06 – 31/10
$180/nighttotal: $22140 (123 )
Entire Home In Dalton, Massachusetts, United States
1 1
cottage , Dalton
This Dalton cottage, situated 1.4 kilometres from the Crane Museum of Papermaking and within 10 kilometres of Wahconah Falls State Park and Bas Ridge Golf Course, offers a convenient base for exploring the Berkshires. Sleeping four guests, this one-bedroom, one-bathroom self-catering property includes in-cottage laundry facilities, a hairdryer and iron, and is perfect for exploring the area's attractions, including the Barrington Stage Company.
9.7 21 reviews
Pittsfield, MA
13/10 – 18/10
$623/nighttotal: $3115 (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.
10 66 reviews
Pittsfield, MA
13/10 – 18/10
$279/nighttotal: $1395 (5 )
Comfy Quaint Tavern
1 3
apartment , Pittsfield
This one-bedroom flat is situated in the southeast section of Pittsfield, a residential area with a couple of restaurants and a seasonal ice cream shop within walking distance. The property has excellent user, location, and cleanliness ratings. The flat is suitable for up to three guests and includes a living room with a queen-sized pull-out sofa. It is equipped with modern amenities such as a dishwasher, air conditioning, and off-street parking, as well as a 12-foot bar with stools for relaxation and a small park across the street for outdoor recreation.
Pittsfield, MA
21/08 – 24/08
$1011/nighttotal: $3033 (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.
Best family friendly Pittsfield, MA vacation rentals
Among the 157 accommodations in Pittsfield, MA, here are the 4 best family friendly rentals
9.9 95 reviews
Pittsfield, MA
06/09 – 13/09
$388/nighttotal: $2716 (7 )
Bb's Central Berkshire Home
1 2
apartment , Pittsfield
This Pittsfield house, situated on a quiet cul-de-sac near walking trails and a playground, offers easy access to Lenox and Lee (24km), Great Barrington (48km), Mass MoCA, Mount Greylock, The Clark Art Institute, and Jiminy Peak (48-72km). The three-bedroom, two-bathroom home sleeps up to ten guests, features a finished basement with a kids' play area, a garden with BBQ and fire pit, and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher; air conditioning and parking are also provided.
Pittsfield, MA
06/09 – 13/09
$582/nighttotal: $4074 (7 )
Pine & Paddle | Pond Access Kayaks
2 2
cottage , Richmond
This two-bedroom flat in Richmond offers a secluded country cottage feel, located a short walk from a private community beach on Richmond Pond and within easy reach of Tanglewood and Bousquet. This pet-friendly residence accommodates up to four guests, featuring a newly renovated kitchen with a fridge and microwave, a wood-burning fireplace, a balcony with woodland views, and access to a tandem kayak for use on the pond, with parking also provided.
10 3 reviews
Pittsfield, MA
13/10 – 18/10
$1050/nighttotal: $5250 (5 )
Lenox Grand Colonial With Pool By Evergreen Home
4 3
apartment , Lenox
This Lenox holiday home is situated in a rural setting, less than 3km from the Housatonic River and the historical Arrowhead, home of Herman Melville. This four-bedroom, three-bathroom property boasts 281 square metres of living space, a private pool, barbecue facilities, and sleeps eight guests, offering free Wi-Fi and a fully equipped kitchen.
10 2 reviews
Pittsfield, MA
12/07 – 18/07
$1071/nighttotal: $6426 (6 )
Perfect Location In The Heart Of Downtown Lenox
3 2
apartment , Lenox
This comfortable house is located just 0.5km from The Bookstore and 2.9km from Tanglewood Music Center, making it easy to access both cultural attractions and the peaceful surroundings of Lenox. It has consistently received excellent user ratings, indicating a positive experience for previous guests. The 167 square metre house has three bedrooms and three bathrooms, accommodating up to six guests comfortably. It offers a range of amenities, including a private patio, a shared garden, barbecue facilities, a fully equipped kitchen, and free Wi-Fi, ensuring a pleasant and convenient stay.
Best Pittsfield, MA vacation rentals with parking
10 109 reviews
Pittsfield, MA
13/10 – 18/10
$1176/nighttotal: $5880 (5 )
Lake Front Home In Heart Of The Berkshires Near Jiminy Peak
4 3
apartment , Pittsfield
This lakeside dwelling is situated just a 20-minute drive from Jiminy Peak Ski Resort, Tanglewood, and the Berkshire Museum, offering easy access to the region's attractions. The property has consistently received excellent ratings for location, cleanliness, and overall user experience. The spacious apartment boasts four bedrooms, four bathrooms, and an additional sleeping area, comfortably accommodating up to 10 guests. Enjoy the lakefront location with direct access to the water, a dock, kayaks, a fire pit, multiple decks, a garden, and a jacuzzi.
10 87 reviews
Pittsfield, MA
12/07 – 18/07
$1278/nighttotal: $7668 (6 )
Enjoy Comfortable Elegance In This Secluded Grand Home Located In Town
5 2
apartment , Lenox
This five-bedroom home is situated in Lenox, just a short walk from the town centre and two miles from Tanglewood, offering a peaceful retreat in a vibrant location. The property has consistently received excellent ratings for user experience, location, and cleanliness. The spacious apartment, spanning 242 square metres, comfortably accommodates nine guests. Amenities include a fully equipped kitchen, a jacuzzi, a garden, a spa, parking, and internet access, ensuring a relaxing and enjoyable stay.
Pittsfield, MA
03/07 – 06/07
$1124/nighttotal: $3372 (3 )
Ski's The Day: Winsome 3-bedroom Mountain Townhome With Ac In Jiminy Peak
3 2
apartment , Hancock
This 3-bedroom townhome in Hancock is located within Jiminy Peak resort, offering walking access to ski slopes, tennis courts, dining, and pools, and is situated 8.9 kilometres from Mount Lebanon Shaker Village and 6.4 kilometres from the Colonial Theatre. This spacious accommodation sleeps up to 8 guests and features a well-equipped kitchen, a furnished deck, and complimentary travel cot and bassinet, with nearby attractions including the Mountain Coaster and Alpine Super Slide.
8.7 5436 reviews
Pittsfield, MA
03/07 – 06/07
$335/nighttotal: $1005 (3 )
Vacation Village In The Berkshires
1 2
resort , Hancock
The Vacation Village in the Berkshires is situated in Hancock, Massachusetts, just a short drive from Jiminy Peak Mountain Ski Resort and surrounded by the scenic beauty of the Berkshires. This resort has received very good ratings for its location, cleanliness, and overall experience. The resort offers a range of comfortable rooms and apartments, all equipped with modern amenities. Guests can enjoy a variety of on-site facilities, including a swimming pool, jacuzzi, fitness center, tennis court, and spa, as well as access to nearby hiking trails, fishing spots, and other outdoor activities.
Frequently Asked Questions about vacation rentals in Pittsfield, MA
What are the top family-friendly attractions in Pittsfield, MA?
The Hancock Shaker Village is a great place to visit with kids, they'll love learning about the Shakers and seeing their historic buildings. The Barrington Stage Company also puts on some fantastic shows that are perfect for families.
What are the best Airbnb and vacation rentals in Pittsfield, MA?
When is the best time to book a vacation rental in Pittsfield, MA?
You'll want to book your vacation rental in advance, especially if you're planning to visit during the peak season, which is usually from June to August.
What are the most popular Airbnbs in Pittsfield, MA?
What events or festivals should visitors check out in and around Pittsfield, MA?
The Pittsfield Summer Festival is a great event to check out, it takes place in August and features live music, food, and activities. You can also check out the Tanglewood Music Festival, which is held in nearby Lenox.
What are the best vacation rentals with a pool in Pittsfield, MA?
What are the best budget-friendly activities in Pittsfield, MA?
There's a lovely walking trail along the Housatonic River, it's a great way to get some exercise and enjoy the scenery. You can also visit the Pittsfield Public Library, it's a beautiful building and they have a great selection of books and events.
What are the best rentals for families and kids in Pittsfield, MA?
What are the best restaurants with local dishes in Pittsfield, MA?
The Red Lion Inn is a classic Pittsfield restaurant, they've been serving up delicious New England fare for over 100 years. You can also check out the No. 6 for some modern American cuisine.
What are the best rentals or Airbnbs with a jacuzzi in Pittsfield, MA?
What are the best walking or cycling routes in Pittsfield, MA?
The Bike Path along the Housatonic River is a great option for a leisurely bike ride, and you can also find some nice walking trails in the Berkshire Natural Resources Council properties.
Are there pet-friendly attractions in Pittsfield, MA?
The Berkshire Botanical Garden is a great place to bring your dog, they have a dedicated dog walking area. Many of the local parks are also pet-friendly.
What are the benefits of choosing a vacation rental in Pittsfield, MA?
Vacation rentals offer more space and privacy than a hotel, and you'll often find that they're a better value for your money, especially if you're travelling with a family or a group of friends.
What are the top sports attractions and facilities in Pittsfield, MA?
The Pittsfield High School has a great sports complex with a football field, baseball diamond, and track. You can also check out the Berkshire County Athletic League for information on local sporting events.
Destinations nearby
Best Pittsfield, MA vacation rentals with a balcony
Pittsfield, MA
30/06 – 31/10
$936/nighttotal: $115128 (123 )
Perfect For Winter Skiing!!
4 1
apartment , Pittsfield
This four-bedroom apartment in Pittsfield is located just 1.6 kilometres from Bousquet Ski Area and within walking distance of Guido's Marketplace, a popular local grocery store. The apartment has four bathrooms, a fully equipped kitchen, a washing machine, a fireplace, a Smart TV with a DVD player, a terrace, and access to a fitness centre and swimming pool.
8.2 6 reviews
Pittsfield, MA
03/07 – 06/07
$631/nighttotal: $1893 (3 )
Cozy Cabin In The Berkshire Resort
2 2
cabin , Hancock
This luxurious Hancock, Massachusetts lodge is situated within a resort, approximately 32 kilometres from both Tanglewood and Cranwell Spa & Golf Club. The 850-square-metre property boasts two bedrooms, two bathrooms, a hot tub, and sleeps eight guests, offering a fully equipped kitchen, private terrace with mountain views, plus access to a pool, fitness centre, and on-site mini-market.
Pittsfield, MA
06/09 – 13/09
$590/nighttotal: $4130 (7 )
Timpani Corners | Private Pond Ac
3 2
cabin , Lenox
This rustic cottage in Lenox offers a serene woodland setting beside a brook on a private quarry pond, with Tanglewood and Bousquet Mountain Ski Area a mere 6-9 minute drive away. This 76 square meter property accommodates up to six guests with three bedrooms, a fully-equipped modern kitchen, high-speed Wi-Fi, and a garden with an outdoor grill, making it an ideal Berkshire retreat for families and pet owners.
9.8 7 reviews
Pittsfield, MA
03/07 – 06/07
$410/nighttotal: $1230 (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.
Best pet friendly Pittsfield, MA vacation rentals
Among the 157 accommodations in Pittsfield, MA, here are the 4 best pet friendly rentals
9.6 5 reviews
Pittsfield, MA
21/08 – 24/08
$1095/nighttotal: $3285 (3 )
Luxurious Historic Farmhouse
1 6
house , Lanesborough
This meticulously restored 1750s New England farmhouse, situated in the Berkshires near Lanesborough, Massachusetts, offers 196 acres of private land bordering the Constitution Hill trail. Sleeping up to 14 guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, ample parking, Wi-Fi, pet-friendly accommodation and access to the entire house and grounds, including hardwood forests and meadows ideal for hiking.
10 3 reviews
Pittsfield, MA
06/09 – 13/09
$543/nighttotal: $3801 (7 )
Timpani Corners | Private Pond • Ac
1 2
cabin , Lenox
This secluded three-bedroom lodge, formerly owned by BSO timpanist Vic Firth, is situated beside a brook on a private quarry pond in Lenox, offering convenient access to Tanglewood (1.4 km), The Mount (1.4 km), and Shakespeare & Company (1.6 km). This family-friendly and pet-friendly accommodation for six guests features air conditioning, high-speed Wi-Fi, a modern kitchen with a fridge, microwave oven, and dishwasher, and a spacious garden with an outdoor grill, with Bousquet Mountain Ski Area (1 km) and Kennedy Park (1 km) nearby for outdoor activities.
Pittsfield, MA
30/06 – 31/10
$442/nighttotal: $54366 (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.
8.0 1 review
Pittsfield, MA
30/06 – 31/10
$590/nighttotal: $72570 (123 )
Grandparents Cottage 250 Steps To The Lake
4 1
cottage , Stockbridge
This West Stockbridge holiday home is ideally situated near Tanglewood (9.6km), the Berkshire Botanical Garden (11.2km), and the Housatonic River (12.8km), offering easy access to Stockbridge's cultural and natural attractions. Sleeping seven guests, this four-bedroom, two-bathroom property boasts Wi-Fi, essential amenities, and a peaceful setting, perfect for exploring the area's numerous attractions including the Frelinghuysen Morris House & Studio and Guido's Marketplace.
