A person snowboarding down a snowy slope.

Compare and book 4 Star hotels in The Berkshires, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires 4 Star Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for The Berkshires 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.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
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.

1. The Williams Inn

The Williams Inn
Williamstown
United States
Soleil
5.268.086 ₫
5.884.452 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Williams Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
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.
A compact living space with a kitchenette, a dining area, and a sofa.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
2.567.268 ₫
2.867.561 ₫ total
includes taxes & fees
15 Oct - 16 Oct
The Central Downtown Inn & Suites
Front of property
Exterior
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A stone fountain surrounded by trees in a park setting.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
9.459.475 ₫
11.094.488 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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
9.897.929 ₫
11.973.672 ₫ total
includes taxes & fees
13 Nov - 14 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A white two-story house with a front door, windows, and a chimney.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

5. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
7.515.640 ₫
9.069.045 ₫ total
includes taxes & fees
10 Nov - 11 Nov
The Old Inn On The Green
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 dining room with a large wooden table, blue upholstered chairs, and a chandelier.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.

6. Seven Hills Inn

Seven Hills Inn
Lenox
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 spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

7. Devonfield Inn B&B

Devonfield Inn B&B
Lee
9.563.004 ₫
10.681.798 ₫ total
includes taxes & fees
13 Nov - 14 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 grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A dining room with a large table set for a meal, surrounded by ornate chairs.

8. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
6.560.796 ₫
7.328.383 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Hampton Terrace Inn
A modern bathroom with a glass shower, white marble walls, and a large window.
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.
A neatly arranged bedroom with a large bed, a chair, and a window with a view of trees.

9. 33 Main

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

10. 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 cozy living room with a fireplace, a large window, and a dining area set for six.

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

Family-friendly Hancock Home: Walk to Slopes!
Hancock
Family-friendly Hancock Home: Walk to Slopes!
Save an average of 15% on thousands of hotels when you're signed in

Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires
A large white building with multiple chimneys, surrounded by lush gardens with various flowers.
Photo by Photo courtesy of Berkshire Visitors Bureau

Top The Berkshires Hotel Reviews

Frequently asked questions

What are the best 4-star hotels in The Berkshires?
If your The Berkshires break takes you to Lenox, consider Hampton Terrace Inn. With a wide range of amenities such as a terrace and a swimming pool, it gets great reviews from many Expedia guests. Another favourite here is Garden Gables Inn. It also has 4 stars and features designer toiletries and dining romance packages.
How much does it cost to stay in a 4-star hotel in The Berkshires?
With Expedia's handy filter tool, landing a top deal on a 4-star hotel in The Berkshires just got simpler. Start by entering your chosen travel dates and length of your escape. Then sort the results by price and pick the option that best fits your budget and style.
  • Search for the lowest price from 2.867.561 ₫
What's the difference between 5-star and 4-star hotels in The Berkshires?
Treat yourself to luxury living during your The Berkshires holiday by checking in to a 4-star hotel. As well as featuring upmarket surroundings, these retreats are usually packed with amenities like large beds, complimentary bathrobes and more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and memorable one. Concierge assistance, elegant décor and world-class dining are only the start of the superior services and conveniences you'll likely get access to.

Explore a world of travel with Expedia