Find 4 Star Hotels in Sheffield, MA from $218

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Check availability on Sheffield 4 Star Hotels

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Dec 8 - Dec 9
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Dec 9 - Dec 10
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Compare Sheffield 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
$195 nightly
The price is $218
Dec 12 - Dec 13
Total with taxes and fees
Lakehouse Inn
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
$349 nightly
The price is $390
Dec 9 - Dec 10
Total with taxes and fees
Devonfield Inn B&B
Front of property
Seven Hills Inn

Seven Hills Inn

4.0 star property
Lenox
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Business center
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

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi
The White Hart

The White Hart

4.0 star property
Salisbury
9.6 out of 10, Exceptional, (143)
"Great charming place, friendly, helpful staff"
United States
David
$254 nightly
The price is $292
Dec 9 - Dec 10
Total with taxes and fees
The White Hart
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds
9 Academy

9 Academy

4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10)
"Nice room. "
South Korea
JeongHoon
$494 nightly
The price is $568
Dec 15 - Dec 16
Total with taxes and fees
9 Academy
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$441 nightly
The price is $493
Jan 8 - Jan 9, 2026
Total with taxes and fees
33 Main
Exterior
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (111)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
United States
Joanna T.
General Williams Estate House Lenox/Stockbridge
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Terrace Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Inn at Stockbridge
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

The Old Inn On The Green

4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
$336 nightly
The price is $368
Dec 9 - Dec 10
Total with taxes and fees
The Old Inn On The Green
Front of property - evening/night
Garden Gables Inn

Garden Gables Inn

4.0 star property
Lenox
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
United States
john
Garden Gables Inn
Outdoor pool
Rock Hall Luxe Lodging

Rock Hall Luxe Lodging

4.5 star property
Winsted
10.0 out of 10, Exceptional, (4)
"The innkeepers were extememly accomadating. They made dinner reservations for us and offered suggestions of activities. Breakfast was fantastic. Before we left, we picked apples from the onsite orchard. Highly reccomended."
United States
Jessica
Rock Hall Luxe Lodging
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Sheffield.
Troutbeck

Troutbeck

515 Leedsville Rd Amenia NY
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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield
FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

Find out more about Sheffield

Sheffield Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Sheffield, Massachusetts are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Sheffield 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Sheffield. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Sheffield, Massachusetts, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Sheffield hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Sheffield?
Expedia can help you quickly find the ideal 4-star hotel for your vacation in Sheffield. Use our handy filter tool to tailor your search by things like price, amenities and property star rating and get access to awesome deals in a couple of clicks.

  • Search for the lowest price from $218

What's the difference between 5-star and 4-star hotels in Sheffield?
Give yourself the luxury treatment during your Sheffield getaway by staying at a 4-star hotel. As well as featuring upscale surroundings, these properties are usually filled with amenities like bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your trip an even more lavish and unforgettable one. 24-hour concierge assistance, elegant furnishings and gourmet dining are only the start of the exclusive conveniences and services you'll likely have access to.
Does Sheffield have any 4-star all-inclusive resorts?
Enjoy a carefree vacation experience where just about everything is included in the one upfront price by using our "All inclusive" filter. Staying within budget is easy when your room, food and many activities are already taken care of. After more options? Browse the terrific deals on Expedia's standard 4-star options in and around Sheffield.

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