Compare Vacation Rentals & Airbnb in Pittsfield, MA
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157 Rentals and Airbnb in Pittsfield, MA
9.8 45 reviews
Pittsfield, MA
13/10 – 18/10
$426/nighttotal: $2130 (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.
10 47 reviews
Pittsfield, MA
01/07 – 31/07
$550/nighttotal: $16500 (30 )
Converted Barn W/pond On 120 Acres
1 1
apartment , East Nassau
This Berkshires farmhouse, situated in East Nassau, is centrally located, approximately 48km from Lenox and Tanglewood, and Williamstown, with North Adams (MASS MoCA) a further 16km away. The property boasts a converted barn offering five bedrooms sleeping up to ten guests, a well-equipped kitchen, a private 120-acre estate with a pond, trout stream, hiking trails, and access to nearby attractions including Cherry Plain State Park and Jiminy Peak.
8.8 8 reviews
Pittsfield, MA
01/07 – 31/07
$319/nighttotal: $9570 (30 )
1st Floor Mountain View Suite Ski On/off At Jiminy- Fully Redone Decor
1 1
apartment , Hancock
This Hancock apartment, near Jiminy Peak Mountain Resort (under 3.2km) and Pittsfield State Forest (under 9.7km), offers ski-in/ski-out access and proximity to the Alpine Super Slide and Mountain Coaster. The 46-square-metre property features two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, indoor pool access, fitness centre, and jacuzzi.
9.5 9 reviews
Pittsfield, MA
03/07 – 06/07
$454/nighttotal: $1362 (3 )
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4
1 2
apartment , Hancock
This Hancock apartment is situated near Jiminy Peak Ski Resort, approximately 55 kilometres from Albany International Airport. The 46-square-metre flat offers one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, free Wi-Fi, a washing machine, and access to an on-site swimming pool, jacuzzi, and fitness centre.
9.8 43 reviews
Pittsfield, MA
21/08 – 24/08
$559/nighttotal: $1677 (3 )
3 Bedroom , 2 Bath, Beautifully Appointed Home
1 6
apartment , Pittsfield
This comfortable home is located in a central Pittsfield neighbourhood, just a short distance from attractions such as Tanglewood, the Norman Rockwell Museum, and Mass MOCA. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It is equipped with a fully equipped kitchen, air conditioning, a garden, and a fitness centre, providing everything you need for a relaxing and enjoyable stay.
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.
9.9 26 reviews
Pittsfield, MA
01/07 – 31/07
$423/nighttotal: $12690 (30 )
Condo On The Mountain
1 1
apartment , Hancock
This three-bedroom Hancock apartment, situated directly on Jiminy Peak resort, offers ski-in/ski-out access and is within walking distance of the Jiminy Peak ski slopes. The three-level condo sleeps six, features a fully equipped kitchen with dishwasher, washer/dryer, two bathrooms, a smart TV, and complimentary refreshments, plus a gift certificate for a local store.
10 16 reviews
Pittsfield, MA
06/09 – 13/09
$462/nighttotal: $3234 (7 )
The Reel Retreat | Theatre & Firepit • Game Room
4 2
apartment , Pittsfield
This three-bedroom Pittsfield apartment, ideal for families or groups of up to seven, is situated a short distance from both Pittsfield and Lenox town centres, offering easy access to the Berkshires' attractions. The property boasts a fully equipped kitchen, a private cinema room, games room, spacious backyard with deck and barbecue, and parking; all within a comfortable dwelling.
9.6 37 reviews
Pittsfield, MA
13/10 – 18/10
$307/nighttotal: $1535 (5 )
Petite Paris
1 3
apartment , Pittsfield
This three-bedroom Pittsfield apartment, ideal for families, offers excellent cleanliness and is located in a quiet neighbourhood, its precise location within Pittsfield unspecified but proximate to local landmarks. Sleeping six guests comfortably, this self-catering flat boasts a fully equipped kitchen including dishwasher, air conditioning, a garden, parking, and excellent user reviews; it is perfect for a relaxing family vacation.
10 3 reviews
Pittsfield, MA
13/10 – 18/10
$282/nighttotal: $1410 (5 )
Cozy Escape To The Berkshires
1 3
apartment , Pittsfield
This two-bedroom flat in Southeast Pittsfield provides a quiet base, conveniently located for accessing Berkshire attractions such as the Clark Art Institute and Tanglewood, as well as skiing and hiking opportunities within a 30 kilometre radius. The accommodation offers a fully equipped kitchen, a king-sized bed and a queen-sized bed, a large bathroom with a walk-in shower, a separate half-bathroom with a washer and dryer, and Smart TVs throughout, comfortably accommodating up to four guests with keyless entry.
9.5 37 reviews
Pittsfield, MA
13/10 – 18/10
$260/nighttotal: $1300 (5 )
Spacious 2 Bedroom Downtown Very Nice Area!
1 3
apartment , Pittsfield
This two-bedroom Pittsfield flat is conveniently located within an 0.8km radius of Pittsfield's main street, offering easy access to numerous amenities, cafes, restaurants, and a cinema. The self-catering property sleeps four guests and features a kitchen, air conditioning, parking, and internet access; enjoy easy walking access to local entertainment and attractions.
9.9 100 reviews
Pittsfield, MA
13/10 – 18/10
$250/nighttotal: $1250 (5 )
Downtown Apartment A
1 3
apartment , Pittsfield
This two-bedroom flat is located in a quiet neighbourhood in Pittsfield, just 5km from Bousquet Ski Area and a short drive from Jimmy Peak, Tanglewood, Mass MoCA, and a variety of restaurants. This property has consistently received excellent ratings for its cleanliness, location, and overall experience. The flat offers ample space for relaxation and privacy, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, air conditioning, parking, and internet access, as well as the convenience of being close to hiking and biking trails, making it an ideal base for exploring the Berkshires.
Best family friendly Pittsfield, MA vacation rentals
Among the 157 accommodations in Pittsfield, MA, here are the 4 best family friendly rentals
9.9 66 reviews
Pittsfield, MA
01/07 – 31/07
$642/nighttotal: $19260 (30 )
Mountainside: Large 3-level Jiminy Peak Home
1 1
apartment , Hancock
This spacious three-level condo, near Jiminy Peak ski resort in Hancock, Massachusetts, offers easy access to Bloom Meadows (under 8 km), Williamstown, Pittsfield, and New Lebanon (all within 24 km), and Mass MoCA (48 km). The 172 square metre property sleeps eight guests in four bedrooms and three bathrooms, boasting a fully equipped kitchen, swimming pool, jacuzzi, garden, fitness centre, and parking, plus resort amenities including an outdoor pool, hot tubs, gym and Mountain Adventure Park.
9.8 12 reviews
Pittsfield, MA
01/07 – 31/07
$254/nighttotal: $7620 (30 )
Mountain View Jiminy Peak Ski On Off Sleeps 4
1 1
apartment , Hancock
This one-bedroom flat is located at the base of Jiminy Peak Mountain in Hancock, providing direct access to resort attractions and situated within 100 meters of Jiminy Peak's Adventure Park. This family-friendly suite accommodates up to four guests and features a king bed, a pull-out queen sofa, a kitchen with a fridge, freezer, microwave oven, and dishwasher, air conditioning, a swimming pool, hot tubs, a fitness centre, and parking.
9.8 21 reviews
Pittsfield, MA
03/07 – 06/07
$672/nighttotal: $2016 (3 )
Cozy Cabin In Berkshires Resort. Ski In And Out. Pet Friendly.
2 2
resort , Hancock
This two-bedroom cabin, part of the 'Cozy Cabin On Resort Property In Cultural Berkshires. Labor Day Sale!' offer, is situated on the Jiminy Peak Ski Resort property in Hancock, Massachusetts, just 30km from MassMoCA and 35km from Tanglewood. The property enjoys excellent user ratings and is perfect for families or groups of up to five people. The 83 square metre cabin is spread across a single floor and includes a living room with a pull-out double bed, two bedrooms with queen-size beds, and two bathrooms. Guests can enjoy a range of amenities including a swimming pool, hot tub, tennis court, fitness centre, and access to mountain biking and skiing activities.
9.9 92 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.
Best Pittsfield, MA vacation rentals with parking
9.8 22 reviews
Pittsfield, MA
03/07 – 06/07
$539/nighttotal: $1617 (3 )
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
1 2
apartment , Hancock
This apartment is located in Hancock, just 0.16 kilometres from Jiminy Peak Mountain Resort, offering easy access to the slopes and nearby attractions like Zema's Nursery and Pittsfield State Forest. It has received excellent user ratings, making it a popular choice for travellers. The apartment has one bedroom and one bathroom, covering 46 square metres and comfortably accommodating up to four guests. It includes a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, parking, and a fireplace, providing all the amenities you need for a relaxing and enjoyable stay.
9.9 83 reviews
Pittsfield, MA
06/09 – 13/09
$597/nighttotal: $4179 (7 )
Berkshire’s Sweet Spot- Pool And Spa
3 2
apartment , Pittsfield
This three-bedroom apartment is located in the heart of Berkshire County, just a short walk from Pittsfield's downtown area and within easy reach of both North and South County attractions. The apartment has been highly rated by previous guests for its cleanliness, location, and overall experience. The apartment spans two floors and comfortably accommodates up to eight guests. Enjoy the private backyard with a seasonal pool, year-round spa, and a shared outdoor space with the other side of the duplex, ideal for larger groups.
Pittsfield, MA
06/09 – 13/09
$654/nighttotal: $4578 (7 )
Dharma Grove - Bask In The Light
3 2
apartment , Richmond
This Richmond flat offers a secluded Berkshire escape on 2.5 acres, located a short drive from Balderdash Cellars (1.6 kilometres), Hancock Shaker Village (6.4 kilometres), Bousquet Mountain Ski Area (14.5 kilometres), Tanglewood (22.5 kilometres), and the Norman Rockwell Museum (27.4 kilometres). This 191 square metre residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, an outdoor grill, high-speed Wi-Fi, and a garden, with pets welcome for a one-time fee.
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.
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
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.
Pittsfield, MA
06/09 – 13/09
$316/nighttotal: $2212 (7 )
Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield
1 2
apartment , Pittsfield
This one-bedroom flat in Pittsfield is conveniently located for exploring local culture and history, with Tanglewood Music Center and Colonial Theater just a short distance away, and Herman Melville's Arrowhead and Hancock Shaker Village also nearby. This apartment offers accommodation for up to four guests, featuring a king-size bed, a sofa bed in the living room, air conditioning, and complimentary Wi-Fi, and is within easy reach of the Berkshire Museum and Bousquet Ski Area.
Pittsfield, MA
06/09 – 13/09
$666/nighttotal: $4662 (7 )
Spacious Historic Home In The Berkshires!
1 2
cottage , Pittsfield
This cottage is located in Pittsfield, within a 10-minute walk of the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, and within 2km of the Housatonic River and Barrington Stage Company. The self-catering property features a fireplace, a fully equipped kitchen with a dishwasher, a balcony, free Wi-Fi, and parking.
8.4 10 reviews
Pittsfield, MA
03/07 – 06/07
$1167/nighttotal: $3501 (3 )
Comfortable Berkshires Retreat On Mtn Resort, Siso
4 2
resort , Hancock
The Comfortable Berkshires Retreat On Mtn Resort, Siso in Hancock, Massachusetts is situated less than 1 kilometre from Jiminy Peak Mountain Resort and within 5 kilometres of family attractions such as the Alpine Super Slide and Mountain Coaster. This four-bedroom holiday home sleeps up to 12 guests and boasts a fully equipped kitchen, fireplace, private fitness centre, sauna, hot tub, and free Wi-Fi, alongside on-site games and a swimming pool.
Best pet friendly Pittsfield, MA vacation rentals
Among the 157 accommodations in Pittsfield, MA, here are the 4 best pet friendly rentals
10 3 reviews
Pittsfield, MA
13/10 – 18/10
$1062/nighttotal: $5310 (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.
9.5 32 reviews
Pittsfield, MA
01/07 – 31/07
$495/nighttotal: $14850 (30 )
3 Br+ 4level Winter Ski Rental\n Looking 4 Seasonal Renter\n 1 Mile Off Of Jiminey
4 1
apartment , Lanesborough
This Lanesborough apartment is situated in a mountain setting, less than 5 kilometres from Jiminy Peak Mountain Resort and Mount Greylock State Reservation. This 163-square-metre property offers four bedrooms, two bathrooms, sleeps ten guests, and boasts a private jacuzzi, terrace, swimming pool, fitness centre, and tennis court, alongside free Wi-Fi.
9.6 21 reviews
Pittsfield, MA
01/07 – 31/07
$702/nighttotal: $21060 (30 )
Home In The Berkshires
4 1
apartment , Hancock
This spacious four-bedroom holiday home is situated on a secluded 1.2-hectare property in Williamstown, Massachusetts, offering convenient access to Jiminy Peak Mountain Resort (800 metres) and the Ashuwillticook Rail Trail (1.6 kilometres). This 186-square-metre residence accommodates up to eight guests, featuring two master suites, a kitchen with a fridge and dishwasher, and a terrace or balcony, with the surrounding Berkshires providing ample opportunities for outdoor pursuits such as hiking, fishing, and kayaking.
9.0 1 review
Pittsfield, MA
06/09 – 13/09
$641/nighttotal: $4487 (7 )
Spacious Historic Home In The Berkshires!
5 2
house , Pittsfield
This spacious five-bedroom house is situated in Pittsfield, Massachusetts, just 12.2 kilometres from Tanglewood and 12.6 kilometres from Cranwell Spa & Golf Club. The 307 square metre property offers ample space for up to 17 guests, with modern amenities such as air conditioning, Wi-Fi, a fully equipped kitchen, and a balcony.
