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

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys! - Pittsfield, MA
9.6 15 reviews
Pittsfield, MA
06/10 – 13/10
SG$335/nighttotal: SG$2345 (7 )

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

2 3
farm , Lenox
This Lenox farmhouse, a family-friendly self-catering holiday home, is situated on a mountainside within 3km of the Housatonic River, Arrowhead, and Herman Melville's Arrowhead.
Sleeping six guests in two bedrooms and one bathroom, this smoke-free property boasts a garden, parking, air conditioning, Wi-Fi, and a kitchen equipped with a fridge and microwave; nearby attractions include Guido's Marketplace and the Pleasant Valley Wilderness Sanctuary.
Cozy Bungalow In Se Pittsfield - Pittsfield, MA
9.9 28 reviews
Pittsfield, MA
06/10 – 13/10
SG$310/nighttotal: SG$2170 (7 )

Cozy Bungalow In Se Pittsfield

1 3
apartment , Pittsfield
This apartment is located in the Berkshires, a short drive from Pittsfield, just 5 km from Bousquet Ski Mountain and 20 km from Jiminy Peak, making it a great choice for those looking to explore the region's natural beauty and outdoor activities. It has received excellent ratings for location, cleanliness, and overall experience.
This single-storey property can accommodate up to 5 guests and offers a comfortable and private stay. It includes a fully equipped kitchen, a garden, a deck and an enclosed porch, as well as access to a grill and yard games, perfect for relaxing and enjoying the outdoors.
Cheerful 3 Bedroom House Abutting State Forest - Pittsfield, MA
Pittsfield, MA
06/10 – 13/10
SG$472/nighttotal: SG$3304 (7 )

Cheerful 3 Bedroom House Abutting State Forest

3 3
house , Lenox
This three-bedroom split ranch in Lenox is located directly beside October Mountain State Forest, offering immediate access to nature and a short drive to Lenox town centre and its cultural attractions including Tanglewood and the Norman Rockwell Museum.
This family-friendly property sleeps six guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, and internet access, with nearby opportunities for hiking, biking, kayaking, and fishing.
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-in, Ski-out Resort - Pittsfield, MA
Pittsfield, MA
01/07 – 31/07
SG$715/nighttotal: SG$21450 (30 )

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-in, Ski-out Resort

1 1
resort , Hancock
Wyndham Bentley Brook, a resort in Hancock, offers direct ski-in, ski-out access to Jiminy Peak slopes, situated within the Berkshire Mountains, with Mount Greylock State Reservation just 8 kilometres away.
This family-friendly accommodation provides 1 bedroom and sleeps up to 8 guests, featuring a swimming pool, Jacuzzi, fitness centre, and tennis court, all part of the "Unleash Your Alpine Adventure" offer.

Best Pittsfield, MA lodgings with a pool

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

Tranquil Lakeside Escape In The Berkshires - Pittsfield, MA
10 1 review
Pittsfield, MA
20/06 – 27/06
SG$533/nighttotal: SG$3731 (7 )

Tranquil Lakeside Escape In The Berkshires

2 2
apartment , Lenox
This Lenox condo, a short 6.4km drive from The Mount and 9.6km from the Housatonic River, offers convenient access to local attractions.
The two-bedroom, three-bathroom apartment sleeps six, boasting a fully equipped kitchen, in-unit laundry, a swimming pool, sauna, parking, and free Wi-Fi.
Brookside Mountain Retreat By Avantstay - Pittsfield, MA
Pittsfield, MA
20/06 – 27/06
SG$2713/nighttotal: SG$18991 (7 )

Brookside Mountain Retreat By Avantstay

13 2
house , East Nassau
This large house for rent in Hancock, East Nassau, is situated 29 kilometres from Tanglewood and 37 kilometres from Rensselaer Polytechnic Institute.
This extensive property offers accommodation for up to 40 guests across 603 square metres, featuring a heated outdoor swimming pool, hot tub, game room, outdoor fire pit, and includes Wi-Fi and private parking.
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4 - Pittsfield, MA
9.5 9 reviews
Pittsfield, MA
01/07 – 31/07
SG$300/nighttotal: SG$9000 (30 )

Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4

1 1
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.
Huge Designer House On 2 Acres Property, Minutes To Restaurants, Museums - Pittsfield, MA
10 6 reviews
Pittsfield, MA
06/10 – 13/10
SG$1271/nighttotal: SG$8897 (7 )

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

1 3
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.

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

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield - Pittsfield, MA
Pittsfield, MA
06/10 – 13/10
SG$275/nighttotal: SG$1925 (7 )

Extended Stay- Full Kitchen 1br Apartment In Downtown Pittsfield

1 3
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.
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat By Avantstay - Pittsfield, MA
Pittsfield, MA
18/06 – 29/06
SG$2703/nighttotal: SG$29733 (11 )

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat By Avantstay

1 2
cottage , East Nassau
This holiday cottage in Stephentown is situated 1.8 kilometres from Taconic Ridge State Forest and within 10 kilometres of Mountain Coaster, Zema's Nursery, Alpine Super Slide, and New Lebanon Town Hall.
Guests at this property can enjoy an outdoor swimming pool, a video game room, barbecues, and complimentary Wi-Fi in common areas, with a well-equipped kitchen, in-unit washer/dryer, patio, and dishwasher provided.
Cozy Escape To The Berkshires - Pittsfield, MA
10 3 reviews
Pittsfield, MA
06/10 – 13/10
SG$250/nighttotal: SG$1750 (7 )

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.
Berkshire Cabin - Pittsfield, MA
10 17 reviews
Pittsfield, MA
01/07 – 31/07
SG$316/nighttotal: SG$9480 (30 )

Berkshire Cabin

1 1
apartment , East Nassau
This secluded Berkshire cottage is situated 11 kilometres from Jiminy Peak Ski Resort and a short drive from Lenox, Pittsfield, Great Barrington, Mount Greylock, and Tanglewood.
The fully renovated one-bedroom, one-bathroom property sleeps two guests and boasts a gourmet kitchen with Wolf stove and Sub-Zero refrigerator, plus access to hiking, snowshoeing, and seasonal activities like apple picking.

Best Pittsfield, MA accommodations with a kitchen

Berkshires Chalet Mins To Tanglewood/lenox - Pittsfield, MA
Pittsfield, MA
18/06 – 29/06
SG$909/nighttotal: SG$9999 (11 )

Berkshires Chalet Mins To Tanglewood/lenox

1 2
apartment , Richmond
This spacious four-bedroom, three-bathroom flat is located in Richmond, approximately 6.4 kilometres from Tanglewood and close to numerous Berkshire attractions, offering convenient access to outdoor pursuits and summer theatre venues.
This modern, open-concept two-storey residence accommodates up to ten guests and features a new kitchen with soapstone counters and stainless steel appliances, air conditioning, a Jacuzzi, a screened porch, and secluded grounds with a covered outdoor hot tub.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.0 1 review
Pittsfield, MA
06/10 – 13/10
SG$638/nighttotal: SG$4466 (7 )

Spacious Historic Home In The Berkshires!

5 3
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.
Mountain View Suite At Jiminy Peak - Ski On Off - Near Elevator, Pool, And Lobby - Pittsfield, MA
9.6 5 reviews
Pittsfield, MA
01/07 – 31/07
SG$293/nighttotal: SG$8790 (30 )

Mountain View Suite At Jiminy Peak - Ski On Off - Near Elevator, Pool, And Lobby

1 1
apartment , Hancock
This Hancock apartment, situated at the base of Jiminy Peak Mountain Resort, offers easy access to Lanesboro, Pittsfield, and North Adams, all within a short driving distance.
The 46-square-metre (495 sq ft) self-catering property sleeps four comfortably, boasting two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher and microwave, plus access to a swimming pool, jacuzzi, and on-site parking; guests can also enjoy the resort's year-round amenities and nearby activities such as skiing and hiking.
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.
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