Places to stay in Pittsfield, MA

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Pittsfield, MA place to stay
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195 Best places to stay in Pittsfield, MA

Best family friendly Pittsfield, MA lodging

Among the 195 accommodations in Pittsfield, MA, here are the 4 best for families

Huge Designer House On 2 Acres Property, Minutes To Restaurants, Museums - Pittsfield, MA
10 6 reviews
Pittsfield, MA
06/09 – 13/09
SG$1444/nighttotal: SG$10108 (7 )

Huge Designer House On 2 Acres Property, Minutes To Restaurants, Museums

1 2
apartment , Lenox
This Lenox designer retreat, a three-bedroom, two-bathroom apartment, is situated in a secluded wooded setting with immediate access to hiking trails, just 3.2 kilometres from Lenox town centre and 3.2 kilometres from a ski resort.
The 232-square-metre property boasts a fully equipped kitchen, spacious sunroom, large-screen movie system, high-speed internet, a saltwater pool, Finnish sauna, and parking, comfortably accommodating six guests and offering easy access to local attractions, festivals, and museums.
Berkshire Mountain Lodge - Pittsfield, MA
8.8 1678 reviews
Pittsfield, MA
13/10 – 18/10
SG$217/nighttotal: SG$1085 (5 )

Berkshire Mountain Lodge

1 3
house , Pittsfield
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.
Converted Barn W/pond On 120 Acres - Pittsfield, MA
10 47 reviews
Pittsfield, MA
01/07 – 31/07
SG$506/nighttotal: SG$15180 (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.
Comfy Quaint Tavern - Pittsfield, MA
10 65 reviews
Pittsfield, MA
13/10 – 18/10
SG$257/nighttotal: SG$1285 (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.

Best Pittsfield, MA lodgings with a pool

Among the 195 accommodations in Pittsfield, MA, here are the 4 best ones with a pool

1st Floor Mountain View Suite Ski On/off At Jiminy- Fully Redone Decor - Pittsfield, MA
8.8 8 reviews
Pittsfield, MA
01/07 – 31/07
SG$293/nighttotal: SG$8790 (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.
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4 - Pittsfield, MA
9.4 10 reviews
Pittsfield, MA
01/07 – 31/07
SG$233/nighttotal: SG$6990 (30 )

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.
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn - Pittsfield, MA
9.8 22 reviews
Pittsfield, MA
03/07 – 06/07
SG$495/nighttotal: SG$1485 (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.
Gorgeous Mountain View Suite Ski On/off At Jiminy - Pittsfield, MA
9.2 5 reviews
Pittsfield, MA
01/07 – 31/07
SG$236/nighttotal: SG$7080 (30 )

Gorgeous Mountain View Suite Ski On/off At Jiminy

1 1
apartment , Hancock
This one-bedroom flat offers direct access to Jiminy Peak Mountain, situated within the Country Inn and boasting exceptional mountain views and proximity to the mountain's base.
This family-friendly accommodation comfortably sleeps four, featuring a kitchenette, a full bathroom, and access to the Country Inn's amenities, including a heated outdoor swimming pool, hot tubs, and fitness centre, ideal for both summer and winter activities.

Frequently asked questions about accommodations in Pittsfield, MA

  • What are the top attractions and must-see sites in Pittsfield, MA?

    Pittsfield is home to the iconic Berkshire Museum, which houses a diverse collection of art, science, and natural history exhibits. You can also visit the historic Colonial Theatre, a beautiful 1903 building that hosts a variety of performances. For art lovers, the Clark Art Institute is a must-see, showcasing an impressive collection of European paintings and sculptures.
  • What are the best accommodations in Pittsfield, MA?

    Among the accommodations in Pittsfield, MA, Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?

    The Pittsfield Summer Festival is a popular event, with live music, food stalls, and family activities. If you're around in September, the Berkshire International Film Festival is a great opportunity to catch independent films and meet filmmakers. For a festive atmosphere, visit the Christmas in the City event in December.
  • What are the best accommodations with a pool in Pittsfield, MA?

  • What are the most convenient modes of transportation within Pittsfield, MA?

    Pittsfield has a decent public transport system, with the Berkshire Regional Transit Authority (BRTA) operating buses throughout the city. However, if you want to explore the surrounding areas, renting a car is the most convenient option. There are several car rental companies available at the Pittsfield Municipal Airport.
  • What are the best accommodations with a jacuzzi in Pittsfield, MA?

  • What outdoor activities and adventures are popular in and around Pittsfield, MA?

    The area around Pittsfield is perfect for outdoor enthusiasts. You can hike in the Mount Greylock State Reservation, the highest point in Massachusetts. For a more relaxed experience, visit the Pontoosuc Lake, where you can go swimming, boating, or fishing. In the winter, you can go skiing or snowboarding at Jiminy Peak Mountain Resort.
  • What are the best accommodations for families and kids in Pittsfield, MA?

    The best accommodations for families and kids in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • What types of accommodations are available in Pittsfield, MA?

    Pittsfield offers a variety of accommodation options, from budget-friendly motels to upscale hotels. There are also several bed and breakfasts and vacation rentals available, especially in the historic districts. You can find accommodation options to suit every budget and preference.
  • What are the best pet friendly accommodations in Pittsfield, MA?

    The best pet friendly accommodations in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • When is the best time to visit Pittsfield, MA?

    The best time to visit Pittsfield is during the summer months, from June to August, when the weather is warm and sunny. However, if you're looking for a more peaceful experience, you can visit in the shoulder seasons, spring or autumn, when the crowds are smaller, and the scenery is stunning.
  • What are the best accommodations with parking in Pittsfield, MA?

    Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the best accommodations with parking in Pittsfield, MA.

  • What local dishes and culinary experiences are a must-try in Pittsfield, MA?

    Pittsfield has a vibrant culinary scene, with several restaurants serving local, seasonal dishes. Try the Berkshire pork at The Red Lion, or the New England clam chowder at The Colonial Restaurant. For a sweet treat, visit The Chocolate Truffle Company and indulge in their delicious handmade chocolates.
  • In which part of Pittsfield, MA should you consider renting accommodation?

    The downtown area is a good choice for those who want to be close to the main attractions, restaurants, and shops. If you prefer a quieter setting, consider staying in the West Side, which has a more residential feel and is close to the Berkshire Museum.

Destinations nearby

Best Pittsfield, MA accommodations with a garden

Ski's The Day: Winsome 3-bedroom Mountain Townhome With Ac In Jiminy Peak - Pittsfield, MA
Pittsfield, MA
03/07 – 06/07
SG$1033/nighttotal: SG$3099 (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.
Condo On The Mountain - Pittsfield, MA
9.9 26 reviews
Pittsfield, MA
01/07 – 31/07
SG$389/nighttotal: SG$11670 (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.
Pondside Glamping At Wyomanock - Pittsfield, MA
9.8 8 reviews
Pittsfield, MA
01/07 – 31/07
SG$116/nighttotal: SG$3480 (30 )

Pondside Glamping At Wyomanock

1 1
glamping , East Nassau
This safari tent accommodation is located at Wyomanock Farm in East Nassau, offering a private 75-acre natural setting with wildlife observation opportunities, just a short walk from essential facilities and parking.
This pet-friendly canvas cabin provides comfortable accommodation for two guests, featuring a queen-sized organic mattress, outdoor cooking amenities like a propane grill, and the option for interactive nature experiences such as wildflower picking.
Pine & Paddle | Pond Access • Kayaks - Pittsfield, MA
9.9 15 reviews
Pittsfield, MA
06/09 – 13/09
SG$488/nighttotal: SG$3416 (7 )

Pine & Paddle | Pond Access • Kayaks

2 2
apartment , Richmond
This two-bedroom flat in Richmond offers a country cottage ambiance with a private community beach on Richmond Pond, situated a short walk from Tanglewood and Bousquet ski area.
This pet-friendly accommodation for four features a wood-burning fireplace, a back balcony with woodland views, and a newly renovated kitchen, with access to a tandem kayak for use on Richmond Pond.

Best Pittsfield, MA accommodations with a kitchen

Jiminy Peak Ski Resort 3 Bd Condo - Pittsfield, MA
Pittsfield, MA
01/07 – 31/07
SG$390/nighttotal: SG$11700 (30 )

Jiminy Peak Ski Resort 3 Bd Condo

1 1
apartment , Hancock
This Jiminy Peak condo is located in Hancock, offering direct access to the resort's amenities and ski slopes, with a private entrance and furnished deck.
This family-friendly three-bedroom, two-bathroom apartment sleeps six and includes a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, fitness centre, and parking, plus a lockable ski closet.
Renovated Jiminy Peak Mountainside Condo\ndesigner Interiors  Walk To Slopes - Pittsfield, MA
Pittsfield, MA
03/07 – 06/07
SG$1256/nighttotal: SG$3768 (3 )

Renovated Jiminy Peak Mountainside Condo\ndesigner Interiors Walk To Slopes

3 2
apartment , Hancock
This three-level condominium in Jiminy Peak's Mountainside district offers convenient walking access to the ski lifts and village, situated within Hancock.
This designer-appointed apartment sleeps eight, featuring three bedrooms including two king suites, four bathrooms, a well-equipped kitchen with a microwave and dishwasher, and parking, with the Jiminy Peak adventure park and Mount Greylock State Reservation nearby.
Home In The Berkshires - Pittsfield, MA
9.6 21 reviews
Pittsfield, MA
03/07 – 06/07
SG$765/nighttotal: SG$2295 (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.
Cozy Berkshire 2br - Pittsfield, MA
Pittsfield, MA
01/07 – 31/07
SG$280/nighttotal: SG$8400 (30 )

Cozy Berkshire 2br

1 1
apartment , Cheshire
This Cheshire studio apartment offers convenient access to the Ashuwillticook Rail Trail and Berkshire County attractions.
The self-contained apartment, sleeping up to two guests, features a full kitchen, handicap-accessible bathroom, private parking, and internet access.
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