Search for Cheap Deals on
4 Star Hotels in Pittsfield

Check Last Minute Pittsfield Hotel Deals

Tonight Sep 27 - Sep 28This weekend Sep 27 - Sep 29

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking, and you save up to 60%!


Featured 4 Star Pittsfield Hotels

The Williams Inn
4 out of 5
Fully refundableReserve now, pay when you stay
  • 49 min drive from Bousquet Ski Area
The price is $334 per night from Sep 30 to Oct 1
$334
includes taxes & fees
Sep 30 - Oct 1
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
The Williams Inn
Lakehouse Inn
4 out of 5
  • 15 min drive from Bousquet Ski Area
Stay at this 4-star beach B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Lakehouse Inn
The Central Downtown Inn & Suites
4 out of 5
  • 5 min drive from Bousquet Ski Area
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
The Central Downtown Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Devonfield Inn B&B
4 out of 5
  • 19 min drive from Bousquet Ski Area
The price is $390 per night from Oct 27 to Oct 28
$390
includes taxes & fees
Oct 27 - Oct 28
Stay at this 4-star golf B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Greenock Country Club ...
Devonfield Inn B&B
Seven Hills Inn
4 out of 5
  • 13 min drive from Bousquet Ski Area
Stay at this 4-star hotel in Lenox. Enjoy free breakfast, free parking, and a garden. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Seven Hills Inn
33 Main
4 out of 5
  • 10 min drive from Bousquet Ski Area
The price is $535 per night from Oct 9 to Oct 10
$535
includes taxes & fees
Oct 9 - Oct 10
Stay at this 4-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Lenox Library are located ...
33 Main
The Inn at Stockbridge
4 out of 5
  • 20 min drive from Bousquet Ski Area
Stay at this 4-star B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and National Shrine of the Divine ...
The Inn at Stockbridge
The Barrington
4 out of 5
  • 37 min drive from Bousquet Ski Area
The price is $363 per night from Oct 2 to Oct 3
$363
includes taxes & fees
Oct 2 - Oct 3
Stay at this 4-star business-friendly B&B in Great Barrington. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mahaiwe Performing ...
The Barrington
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The price is $555 per night from Sep 30 to Oct 1
$555
includes taxes & fees
Sep 30 - Oct 1
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hampton Terrace Inn
4 out of 5
  • 10 min drive from Bousquet Ski Area
Stay at this 4-star hotel in Lenox. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tanglewood Music Center and Ventfort Hall Mansion ...
Hampton Terrace Inn
Garden Gables Inn
4 out of 5
  • 9 min drive from Bousquet Ski Area
Stay at this 4-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and The Bookstore are located ...
Garden Gables Inn
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

4-star hotels in Pittsfield

When you want to live it up, but not bust your bank account, then there’s nothing better than a 4-star hotel in Pittsfield for your next trip. You’ll get all the amenities you can think of (and then some) at a rate within your means.

No fault in our stars

So what’s with the star rating anyway? Good question. The star rating has little to do with the price, and more to do with the amenities. 4-Star hotels in Pittsfield as well as everywhere else, usually have all those thoughtful touches that make you go “Ooh,” “Ahh,” and ”YES!” Think amenities like luxury bedding, high-end electronics, concierge service, and restaurants that make eating in a gourmet experience.

Stars that shine

You know there are as many underground spots, inviting lounges, memory-making music venues as there are stars in the sky. But you’ll need the funds to check them all off. That’s why we give you the chance to take us up on the Hotwire Hot Rate. You can snag Pittsfield 4-star hotels and still have plenty of leftover cash to paint the town whatever color you want. Filter hotels by:

  • Hotwire Hot Rate: We’ll snag you a crazy deal on a room by finding your hotel name after you book.
  • Price: You know that paying full price is for suckers? You can get a cheap 4-star hotel in Pittsfield starting at $334 per night.
  • Amenities: What makes you flip for your trip? Full-service spa? Heated pool? 24-hour room service? Get a hotel that’ll send you over the moon.

Do you deserve a swanky hotel with a ton of amenities? Yes, yes you do. And you also deserve a sweet deal on it. Book with Hotwire today and get that star-studded Pittsfield 4-star hotel and have plenty of cash left over to spend at that secret super star joint in the city.