Find Luxury Hotels in Pittsfield, MA

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Check availability on Pittsfield Luxury Hotels

Top Pittsfield Luxury Hotels

Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
  • Concierge services
9.6 out of 10, Exceptional, (798)
Sophisticated comfort defines this beautifully decorated Pittsfield retreat. Spacious, elegantly appointed rooms feature plush bedding and premium amenities, while the on-site restaurant serves excellent cuisine. Concierge services anticipate every need, creating a luxurious mountain getaway experience.
The price is NT$4,644
NT$5,187 total
includes taxes & fees
Nov 20 - Nov 21
Hotel On North
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (962)
Sophisticated comfort awaits in the heart of Pittsfield. Steps from the Berkshire Museum and Colonial Theater, this refined retreat offers a heated indoor pool, full-service restaurant with exceptional cuisine, and spacious accommodations with thoughtful touches for discerning travelers.
The price is NT$2,749
NT$3,070 total
includes taxes & fees
Nov 21 - Nov 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
8.6 out of 10, Excellent, (345)
Sophisticated comfort awaits in individually furnished suites featuring separate dining areas and premium bath amenities. Steps from Berkshire Museum and minutes from Shakespeare and Company, this upscale retreat combines elegant accommodations with thoughtful luxuries for discerning travelers.
The price is NT$2,783
NT$3,109 total
includes taxes & fees
Nov 23 - Nov 24
The Central Downtown Inn & Suites
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
8.6 out of 10, Excellent, (1000)
Luxury awaits at this tranquil mountain hideaway. Spacious, individually decorated rooms create perfect relaxation spaces with premium amenities. Guests love the peaceful atmosphere, enhanced by fireplaces and jetted tubs that transform ordinary stays into indulgent escapes.
The price is NT$2,039
NT$2,278 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Plus Berkshire Hills Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
  • Laundry
  • Housekeeping
5.4 out of 10, (810)
Luxurious tranquility awaits at this suburban sanctuary where peaceful rooms create a perfect home base. Thoughtfully appointed accommodations feature refrigerators and flat-screen TVs. Located minutes from cultural attractions like the Crane Museum of Papermaking and Barrington Stage Company.
The price is NT$2,337
NT$2,611 total
includes taxes & fees
Nov 23 - Nov 24
FairBridge Inn Express
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.
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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities "
Teresa 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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Frequently asked questions

Are you looking for a luxury hotel for your stay in Pittsfield?
Use Expedia to arrange your flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) airport, and then select from a variety of places to stay that will deliver the luxury you want. 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. While you're visiting, you might want to think about enjoying the entertainment and sporting events, which Pittsfield is known for.
When can I expect good weather in Pittsfield?
Planning for the weather is an important factor for making your trip to Pittsfield a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Pittsfield?
Enjoy all that Pittsfield has to offer when you visit Berkshire Museum, Colonial Theater, and Bousquet Ski Area. If you have spare time during your trip, you might want to make a stop at Hancock Shaker Village and Housatonic River.
How can I get around Pittsfield?
It's easier to get around town in style when you know your options. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.