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Browse for Pittsfield Luxury Hotels from $69

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Travelers Enjoyed These Luxury Hotels

Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
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4.7/5Exceptional! (266 reviews)

"Loved the unique decor of each room and nice touches not found elsewhere"…"

Reviewed on Feb 17, 2020

Hotel On North
Yankee Suites Extended Stay
4 out of 5
20 W Housatonic St., Pittsfield, MA
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4.4/5Excellent! (147 reviews)
Great choice

"Attractive, convenient, clean and welcoming. Plenty of room to be comfortable. Nice deck to enjoy in better weather. Well run. Hope to stay again on future trips."…"

Reviewed on Feb 22, 2020

Yankee Suites Extended Stay
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free CancellationReserve now, pay when you stay
The price is $96 per night
4.2/5Very Good! (657 reviews)

"Conveniently located and super friendly staff! Would come here again"…"

Reviewed on Mar 2, 2020

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires
3.5 out of 5
One West Street, Pittsfield, MA
Free Cancellation
The price is $103 per night
4/5Very Good! (99 reviews)

"Had a great time"…"

Reviewed on Mar 23, 2020

Holiday Inn & Suites Pittsfield-Berkshires
Econo Lodge
1.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is $69 per night
2.8/5 (314 reviews)
Wonderful staff

"Great stay overall"…"

Reviewed on Feb 21, 2020

Econo Lodge
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Looking for a great accommodation for your luxury trip to Pittsfield? Expedia can help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Pittsfield has to offer. During your visit, you might want to enjoy the entertainment and sporting events which Pittsfield is known for.

When to Visit Pittsfield

Here's what you can expect the weather to be like while you are staying in Pittsfield:

  • Hottest months: July, August, June, and September, with an average temperature of 77°F
  • Coldest months: January, February, December, and March, with an average temperature of 14°F
  • Driest months: February, January, December, and March, with an average rainfall of 2.99 inches
  • Rainiest months: October, June, July, and May, with an average rainfall of 4.40 inches

Exploring Pittsfield

Enjoy all that Pittsfield has to offer and visit Berkshire Museum, Berkshire Athenaeum, and Colonial Theater. If you have extra time while you’re in the area, you might want to see Canoe Meadows Wildlife Sanctuary and Bousquet Ski Area.

A few other things that make Pittsfield special are the:
  • Baseball
  • Entertainment
  • Theater
  • Opera
  • Museums
  • Biking
  • Skiing
  • Historical sites

Getting Around Pittsfield

Take advantage of local transportation options that make it easy to see Pittsfield. To explore the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.

Frequently asked questions

Are you looking for a luxury hotel for your stay in Pittsfield?
Arrange a flight into Albany, NY (ALB-Albany Intl.) Airport or Pittsfield, MA (PSF-Pittsfield Municipal) Airport, and then treat yourself to a stay at one of 6 luxurious hotels. During your visit, you might want to enjoy the entertainment and sporting events which Pittsfield is known for.
What's the best luxury accommodation in Pittsfield?
Yankee Suites Extended Stay is a 4-star guesthouse with in-room kitchens, and a popular choice for Expedia travelers looking for a luxurious stay.
What's the seasonal weather like in Pittsfield?
The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 26°F. Average annual rainfall for Pittsfield is 45 inches.
What's there to see and do in Pittsfield?
Enjoy all that Pittsfield has to offer when you visit Berkshire Museum, Bousquet Ski Area, and Pittsfield State Forest. If you have spare time during your trip, you might want to make a stop at Hancock Shaker Village and Colonial Theater.
What's the best way to get around Pittsfield?
Take advantage of local transportation options that make it easy to see Pittsfield. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.

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