Places to stay in Pittsfield, MA

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.

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.

This Berkshire County colonial-style house, situated atop a hill overlooking October Mountain, is 11km from Pittsfield and 11km from Lenox, offering easy access to Bousquet Mountain Ski Area.
This 334 square metre property sleeps ten guests in five bedrooms and three bathrooms, boasting a well-equipped kitchen, jacuzzi, fitness centre, and extensive outdoor space including a hot tub, fire pit, and stone patio; additional amenities include a games room with pool table and ping pong table.

This pet-friendly apartment is located in Pittsfield, just 8km from Pittsfield State Forest and 5km from the Crane Museum of Papermaking, offering easy access to outdoor activities and local attractions. The apartment is suitable for families and groups, accommodating up to 6 guests in 3 bedrooms and 2 bathrooms.
The apartment comes fully equipped with a kitchen, a washer and dryer, a private patio, a fireplace and a barbecue, providing everything you need for a comfortable and enjoyable stay. You can also enjoy Wi-Fi, a Smart TV, air conditioning, and a work desk.

Berkshire Mountain Lodge is conveniently located in Pittsfield, just a short drive from popular attractions like Berkshire Museum, Barrington Stage Company, and Tanglewood. This property has received very good user ratings and excellent location ratings, making it a popular choice for travellers.
This lodge offers a comfortable one-bedroom, one-bathroom accommodation with a full kitchen, a sofa bed for extra guests, and a private bathroom with hairdryer and free toiletries. Enjoy a range of amenities including an indoor swimming pool, a fitness centre, a hot tub, a games room, free Wi-Fi, and a restaurant and bar on-site.

This charming colonial home is situated in a central location in the Berkshires, just 16 kilometres from Tanglewood and 48 kilometres from Jiminy Peak, offering easy access to Pittsfield's attractions. The property has consistently received excellent ratings for its cleanliness, location, and user experience.
The apartment spans 362 square metres and comfortably accommodates up to 12 guests across its four bedrooms. A modern kitchen, a private garden, and a fitness centre are just some of the amenities that guarantee a comfortable and enjoyable stay.

This three-bedroom flat offers a prime location on the Pittsfield/Lenox border, providing convenient access within a 5 to 10-minute drive to shops, ski resorts, restaurants, and art venues in the Berkshires.
This property accommodates up to five guests and features two porches with scenic views of the Berkshire Hills, alongside amenities such as internet, a kitchen, air conditioning, and parking.

This family-friendly apartment in Pittsfield is located just 1.6 kilometres from the Ashuwillticook Rail Trail and 12.8 kilometres from Pittsfield State Forest, offering convenient access to outdoor pursuits and winter sports at Bousquet Mountain Ski Area (12.8 km) and Jiminy Peak Mountain Resort (19.2 km), with Park Square and the Berkshire Museum approximately 6.4 kilometres away.
This spacious accommodation sleeps up to 10 guests across 3 bedrooms and 3 bathrooms, featuring a full kitchen with two ovens and a Crockpot, air conditioning, a fireplace, a deck, balcony, gazebo, and a main-level bedroom and bathroom for accessibility, alongside family amenities like a high chair and Pack 'n Play for a comfortable stay.

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.

This Richmond flat offers a peaceful retreat on Richmond Pond, situated approximately 24 kilometres from downtown Lenox and in close proximity to Balderdash winery.
This two-bedroom flat accommodates up to four guests and features a kitchen, air conditioning, parking, and a fireplace, with opportunities for dining, shopping, hiking, and biking nearby.

This one-bedroom apartment is situated in the centre of Pittsfield, within walking distance of the city's main attractions and restaurants.
The newly renovated apartment features a fully equipped kitchen, a jacuzzi, and a private parking space in the backyard, making it perfect for a couple seeking a comfortable and stylish stay.

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.

This seven-bedroom Pittsfield holiday home is conveniently located within a 1.6km walk of the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, and under 1.6km from the Housatonic River and Barrington Stage Company.
This spacious 307 square metre property sleeps nine guests and boasts a fully equipped kitchen, two bathrooms, laundry facilities, a fireplace, terrace, garden, and parking, all within easy reach of Pittsfield's cultural attractions and transport links.