A historic building with classical architecture, a traffic light, and a yellow taxi.

Compare and book 4 Star hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield 4 Star Hotels

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Pittsfield 4-star hotels

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious living area with a fireplace, wooden beams, and a large window.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

1. The Williams Inn

The Williams Inn
Williamstown
United States
Pete
£170
includes taxes & fees
9 Nov - 10 Nov
The Williams Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A compact living space with a kitchenette, a dining area, and a sofa.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Debra
£83
includes taxes & fees
22 Oct - 23 Oct
The Central Downtown Inn & Suites
Front of property
A stone fountain surrounded by trees in a park setting.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A living room with a fireplace, leather sofas, and a dog.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
£320
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

4. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
£339
includes taxes & fees
12 Nov - 13 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
An indoor dining area with a central table and chairs, surrounded by a decorative archway and greenery.
A large, white, multi-story house with a symmetrical design, surrounded by lush greenery and trees.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.
A room with a large bay window, a wooden bench with cushions, and a chandelier.

5. Seven Hills Inn

Seven Hills Inn
Lenox
United States
Christopher
Seven Hills Inn
A large, two-story house with a well-maintained lawn and a fence.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

6. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
£308
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
£183
includes taxes & fees
17 Nov - 18 Nov
Hampton Terrace Inn
A modern bathroom with a glass shower, white marble walls, and a large window.
A neatly arranged bedroom with a large bed, a chair, and a window with a view of trees.
A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.
A room with a large bed, a chair, and a decorative hanging light fixture.

8. 33 Main

33 Main
Lenox
United States
Tatyana
33 Main
A wooden deck with wicker furniture and a view of a lake.
A two-story house with a balcony, a front porch, and a well-maintained lawn.
A view of a lakeside property with a deck and a white building.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

9. Lakehouse Inn

Lakehouse Inn
Lee
United States
Kathleen
Lakehouse Inn
A deck with outdoor furniture, a hot tub, and a grill.
A spacious living area with a brown leather sectional sofa, a wooden coffee table, and a dining area with wooden chairs and a bar.
A bedroom with a large bed, a nightstand, a painting, and a view of the outside.
A kitchen with wooden cabinets, a stainless steel refrigerator, a window with a view of greenery, and a countertop with various items.

10. Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!
Hancock
Family-friendly Hancock Home: Walk to Slopes!
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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield
A historic building with a clock, a flag, and a street lamp.

Top Pittsfield Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Fantastic hotel! Would definitely stay again."
Pete 1-night trip
Posted 17 hours ago
The Williams Inn
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"I liked the location and the restaurant was good"
Miguel 1-night trip
Posted 2 days ago
The Central Downtown Inn & Suites

Find out more about Pittsfield

Frequently asked questions

What are the best 4-star hotels in Pittsfield?
Garden Gables Inn is a 4-star hotel in Pittsfield that's popular among Expedia customers. Concierge services and designer toiletries are a couple of its amenities. Travellers also love staying at Hampton Terrace Inn. From a swimming pool to premium bedding, it offers conveniences that cater to all aspects of your relaxation and entertainment.
How much does it cost to stay in a 4-star hotel in Pittsfield?
With Expedia's handy search filters, locking in a top deal on a 4-star hotel in Pittsfield just got easier. Start by keying in your chosen arrival date and length of your getaway. Then sort the results by price and pick a hotel that best matches your style and budget.
  • Search for the lowest price from £83
What's the difference between 5-star and 4-star hotels in Pittsfield?
If you decide to stay at a 4-star hotel in Pittsfield, you'll usually find lots of amenities to ensure you're comfortable, such as a pool, restaurant and gym. You can enjoy high-quality service and upscale surroundings. Opt for a 5-star hotel and you'll have access to a few extra bells and whistles — think on-site spas, concierge assistance and nightly turndown services. You're likely to get additional amenities and exclusive services at a 5-star stay, though both are superb options for luxury travellers.

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