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Check availability on Pittsfield Luxury Hotels

Check prices for these dates

Tonight
Jul 15 - Jul 16
Tomorrow
Jul 16 - Jul 17
This weekend
Jul 18 - Jul 20
Next weekend
Jul 25 - Jul 27

Top Pittsfield Luxury Hotels

Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
$189 nightly
The price is $211
Jul 21 - Jul 22
Total includes taxes and fees
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (821)
"Very convenient location, downtown, short drive to local attractions "
$129 nightly
The price is $144
Jul 27 - Jul 28
Total includes taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (297)
"Friendly staff, clean and perfect for a trip with the pups! "
$119 nightly
The price is $133
Jul 16 - Jul 17
Total includes taxes and fees
The Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"Very nice stay"
$127 nightly
The price is $141
Jul 27 - Jul 28
Total includes taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (741)
"Close to our target event a plus"
$71 nightly
The price is $80
Jul 31 - Aug 1
Total includes taxes and fees
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.

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfieldand its attractions for luxury travelers

Pittsfield, Massachusetts, offers a sophisticated blend of culture and natural beauty, perfect for luxury travelers seeking an upscale experience. Begin your journey at the Berkshire Museum, where you can admire a diverse collection of art, science exhibits, and local history, all housed in a beautifully restored building. Just a short drive away, Tanglewood, the summer home of the Boston Symphony Orchestra, beckons with its stunning outdoor amphitheater, where you can enjoy world-class performances amidst the picturesque backdrop of the Berkshires. For art enthusiasts, the Norman Rockwell Museum is a must-visit, showcasing the iconic works of one of America's greatest illustrators in a serene, wooded setting. If relaxation is your goal, indulge in a spa day at one of the area's luxurious hotels, where you can enjoy personalized treatments and top amenities. For a taste of local flavor, savor exquisite dining experiences at upscale restaurants featuring farm-to-table cuisine. Staying in downtown Pittsfield positions you near these attractions, allowing for leisurely strolls to boutique shops and vibrant cultural venues, ensuring you feel pampered and well taken care of throughout your stay.

Find the best luxury hotels and resorts in Pittsfield

For travelers seeking a luxurious escape in Pittsfield, Massachusetts, these top hotels offer exquisite experiences and upscale amenities that define sophistication.

The Central Downtown Inn & Suites

  • Why it's great for a luxury retreat: The Central Downtown Inn & Suites is an exceptional choice for luxury travelers looking for comfort and style, an impressive guest review rating of 8.8. This hotel stands out with its elegant air-conditioned rooms and a range of in-room amenities that elevate the guest experience, ensuring a restful stay with all the comforts of home.
  • Other amenities: Guests can enjoy a delightful terrace perfect for relaxation, and spacious rooms equipped with a kitchen, oven, and dishwasher for those who prefer to dine in. Additional conveniences include daily housekeeping, free toiletries, and self-parking. For those seeking adventure, nearby skiing locations provide the perfect opportunity for winter sports enthusiasts.
  • Nearby attractions: Colonial Theater - 0.43 miles, Berkshire Athenaeum - 0.39 miles, Berkshire Museum - 0.21 miles

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.
What's the best luxury accommodation in Pittsfield?
Yankee Suites Extended Stay is a 4-star guesthouse with a terrace, and a popular choice for Expedia travelers looking for a luxurious stay.
How many luxury hotels should I expect to find in Pittsfield?
Lie in the lap of luxury during your getaway to Pittsfield in one of Expedia's 8 luxury hotels.
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 Barrington Stage Company. If you have spare time during your trip, you might want to make a stop at Herman Melville's Arrowhead and Bousquet Ski Area.
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.