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.
Pittsfield, MA
06/09 – 13/09
1481 €/nightTotal: 10367 € (7 )
Elegant 6-br Berkshires Estate 10 Min To Bousquet
6 2
apartment , Pittsfield
This spacious six-bedroom flat in Pittsfield is situated in the mountains, a mere 644 metres by car from the Colonial Theatre and the Berkshire Museum. This property offers 725 square metres of living space for up to 14 guests, featuring a full kitchen, Wi-Fi, air conditioning, a private garden, and access to shared swimming pool and hot tub facilities.
10 3 reviews
Pittsfield, MA
13/10 – 18/10
175 €/nightTotal: 875 € (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.
10 18 reviews
Pittsfield, MA
13/10 – 18/10
261 €/nightTotal: 1305 € (5 )
Beautiful & Serene Getaway
1 3
apartment , Pittsfield
This three-bedroom apartment in Pittsfield, Massachusetts, is situated in a peaceful neighbourhood a few minutes' drive from the city centre and within easy reach of cultural attractions such as Tanglewood and Mass MoCA. The self-catering property sleeps seven guests and features a spacious living area, a fully equipped kitchen with a fridge, private enclosed backyard with porch and grill, plus free on-site parking and internet access.
10 66 reviews
Pittsfield, MA
06/09 – 13/09
141 €/nightTotal: 987 € (7 )
Comfy Quaint Tavern
1 2
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.
9.8 7 reviews
Pittsfield, MA
30/06 – 31/10
166 €/nightTotal: 20418 € (123 )
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4
1 1
apartment , Hancock
This Hancock, Massachusetts apartment is located at the base of Jiminy Peak Mountain Resort, offering easy access to Lanesboro, Pittsfield, and North Adams, all within a short driving distance. This 46 square metre (approximately 495 square feet) self-catering flat features a unique gamer-themed design, sleeps four guests, and includes a fully equipped kitchenette, a PlayStation 4, and access to Jiminy Peak's amenities such as a heated swimming pool and hot tub.
Pittsfield, MA
12/07 – 18/07
259 €/nightTotal: 1554 € (6 )
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.
9.5 4 reviews
Pittsfield, MA
03/07 – 06/07
199 €/nightTotal: 597 € (3 )
Huttopia Berkshires
1 2
tent , 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.
9.9 83 reviews
Pittsfield, MA
13/10 – 18/10
316 €/nightTotal: 1580 € (5 )
Berkshire’s Sweet Spot- Pool And Spa
3 3
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.
8.4 10 reviews
Pittsfield, MA
03/07 – 06/07
722 €/nightTotal: 2166 € (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.
9.5 37 reviews
Pittsfield, MA
13/10 – 18/10
161 €/nightTotal: 805 € (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.
9.6 37 reviews
Pittsfield, MA
13/10 – 18/10
183 €/nightTotal: 915 € (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.
Best family friendly Pittsfield, MA holiday rentals
Among the 157 accommodations in Pittsfield, MA, here are the 4 best family friendly rentals
9.4 10 reviews
Pittsfield, MA
30/06 – 31/10
138 €/nightTotal: 16974 € (123 )
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4
1 1
apartment , Hancock
This family-friendly apartment, situated at the base of Jiminy Peak Mountain in Hancock, Massachusetts, offers direct access to the Country Inn and its amenities, including a heated pool and fitness centre. The 50 sq m self-catering suite sleeps four, featuring a King bed, a queen sofa bed, a well-equipped kitchenette with appliances including an air fryer and dishwasher, and unique gamer-themed décor including a PS4 and arcade game.
9.6 18 reviews
Pittsfield, MA
13/10 – 18/10
295 €/nightTotal: 1475 € (5 )
Lovely Ranch Home Getaway In The Berkshires- Just 6 Miles To Tanglewood
2 3
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.
10 4 reviews
Pittsfield, MA
30/06 – 31/10
148 €/nightTotal: 18204 € (123 )
Deluxe Mountain View Nautical Suite Jiminy Ski On/
1 1
apartment , Hancock
This one-bedroom flat offers direct ski-in/ski-out access to Jiminy Peak Mountain in Hancock, providing unparalleled convenience for winter sports enthusiasts and immediate proximity to the resort's adventure park attractions. This Pirate luxury-themed apartment comfortably sleeps up to four guests, featuring a fully equipped kitchenette with a Keurig coffee maker and air fryer, along with access to resort amenities including a year-round heated outdoor swimming pool, hot tubs, and a fitness centre.
9.8 21 reviews
Pittsfield, MA
03/07 – 06/07
334 €/nightTotal: 1002 € (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 Pittsfield, MA holiday rentals with parking
10 2 reviews
Pittsfield, MA
12/07 – 18/07
662 €/nightTotal: 3972 € (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.
9.8 22 reviews
Pittsfield, MA
30/06 – 31/10
166 €/nightTotal: 20418 € (123 )
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
1 1
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.
Pittsfield, MA
30/06 – 31/10
580 €/nightTotal: 71340 € (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.
8.8 8 reviews
Pittsfield, MA
03/07 – 06/07
333 €/nightTotal: 999 € (3 )
1st Floor Mountain View Suite Ski On/off At Jiminy- Fully Redone Decor
1 2
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.
Frequently asked questions about holiday rentals in Pittsfield, MA
Which neighborhood in Pittsfield, MA should you consider for a vacation rental?
The area around the Berkshire Museum and the downtown area is a good choice for a vacation rental. It's within walking distance of lots of shops, restaurants and attractions. Plus, it's a bit quieter than some of the busier areas.
What are the best Airbnb and holiday rentals in Pittsfield, MA?
What are the top family-friendly attractions in Pittsfield, MA?
The Hancock Shaker Village is a great day out for all ages. You can explore the historic buildings, learn about Shaker life and even try some traditional crafts. The Berkshire Botanical Garden is another good option. It's a beautiful space with lots of different gardens to explore, plus there are often events and activities for kids.
What are the most popular Airbnbs in Pittsfield, MA?
When is the best time to book a vacation rental in Pittsfield, MA?
The best time to book a vacation rental is during the shoulder seasons, in the spring or autumn. The weather is still pleasant, but the crowds are smaller and prices tend to be lower. If you're looking for something specific, like a particular event, you might want to book earlier.
What are the best holiday rentals with a pool in Pittsfield, MA?
What are the best budget-friendly activities in Pittsfield, MA?
The Berkshire Scenic Railway is a great way to see the area without breaking the bank. You can take a scenic train ride through the beautiful Berkshire Mountains. The Pittsfield Public Library is another free option. It's a beautiful building with a great selection of books and other resources.
What are the best rentals for families and kids in Pittsfield, MA?
What are the best restaurants with local dishes in Pittsfield, MA?
For a taste of local cuisine, head to The Red Lion Inn. It's a historic inn with a menu featuring classic New England dishes. The Colonial Theatre is another good option, with a menu featuring fresh, seasonal ingredients.
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 Berkshire Scenic Railway Trail is a great option for both walking and cycling. It's a paved trail that runs for 10 miles through the beautiful Berkshire Mountains. The Pittsfield Greenway is another good choice, with a network of trails that connect different parts of the city.
Are there pet-friendly attractions in Pittsfield, MA?
The Berkshire Botanical Garden is pet-friendly, so you can bring your furry friend along for a walk through the beautiful gardens. The Pittsfield Public Library also welcomes well-behaved dogs.
What are the benefits of choosing a vacation rental in Pittsfield, MA?
Vacation rentals often offer more space and privacy than hotels. They can also be a more affordable option, especially if you're travelling with a group. And, you'll often have access to amenities like a kitchen and laundry facilities, which can be very convenient.
What are the top sports attractions and facilities in Pittsfield, MA?
The Berkshire County Athletic League is a great option for those interested in sports. It offers a variety of sports leagues and tournaments. The Pittsfield YMCA is another good option, with a range of fitness classes and activities.
Destinations nearby
Best Pittsfield, MA holiday rentals with a balcony
Pittsfield, MA
06/09 – 13/09
360 €/nightTotal: 2520 € (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.
9.6 21 reviews
Pittsfield, MA
03/07 – 06/07
515 €/nightTotal: 1545 € (3 )
Home In The Berkshires
4 2
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.
Pittsfield, MA
06/09 – 13/09
405 €/nightTotal: 2835 € (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.
10 109 reviews
Pittsfield, MA
13/10 – 18/10
728 €/nightTotal: 3640 € (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.
Best pet friendly Pittsfield, MA holiday rentals
Among the 157 accommodations in Pittsfield, MA, here are the 4 best pet friendly rentals
8.2 6 reviews
Pittsfield, MA
03/07 – 06/07
391 €/nightTotal: 1173 € (3 )
Cozy Ski In Out Cabin In 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.
10 45 reviews
Pittsfield, MA
13/10 – 18/10
596 €/nightTotal: 2980 € (5 )
Lenox Grand Colonial With Pool By Evergreen Home
4 3
apartment , Lenox
This spacious Lenox house, situated on a quiet cul-de-sac, is 1.6km from downtown Lenox and Tanglewood, and 0.3km from shops and restaurants, offering easy access to Berkshire attractions including Bousquet Ski Area (5 minutes away). The 279 sq m property boasts four bedrooms sleeping eight, a fully equipped kitchen, a private pool, a large primary bedroom with jacuzzi, plus amenities such as a Weber grill, ping pong, and access to major streaming services; ideal for families or groups.
10 3 reviews
Pittsfield, MA
06/09 – 13/09
336 €/nightTotal: 2352 € (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.
10 3 reviews
Pittsfield, MA
13/10 – 18/10
657 €/nightTotal: 3285 € (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.
