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A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Find 4 Star Hotels in Sheffield, MA from $209

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Check prices for these dates, December 15 – 16, 2026

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Our top choices for Sheffield 4-star hotels

1. The White Hart

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

Location: Salisbury
Guest rating: 9.8/10 (Exceptional, 156 reviews)
Price: $298 nightly, $343 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: It’s an exceptional place in every aspect. , by William

2. Seven Hills Inn

A room with a purple upholstered sofa, a white round table, and a vase with white flowers.

Location: Lenox
Guest rating: 7.8/10 (Good, 467 reviews)
Review: Great location, nice breakfast and clean rooms, by Christopher

3. Devonfield Inn B&B

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Location: Lee
Guest rating: 10/10 (Exceptional, 141 reviews)
Price: $369 nightly, $412 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: Wonderful location and hosts are amazing. Breakfast was great. Clean., by Sebastien

4. Hampton Terrace Inn

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.

Location: Lenox
Guest rating: 9/10 (Wonderful, 45 reviews)
Price: $230 nightly, $257 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: Comfortable bed. Quiet location. Excellent breakfast. Friendly host., by Kathleen

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

A two-story house with a brick entrance and a white facade.

Location: Stockbridge
Guest rating: 9.4/10 (Exceptional, 121 reviews)
Price: $414 nightly, $462 total, Nov 28 - Nov 29, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood., by Philippe

6. The Old Inn On The Green

A dining area with round tables set for two, a fireplace, and a mural on the wall.

Location: Great Barrington
Guest rating: 9.2/10 (Wonderful, 96 reviews)
Price: $319 nightly, $350 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!, by mary ellen

7. 33 Main

A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.

Location: Lenox
Guest rating: 10/10 (Exceptional, 77 reviews)
Review: Beautiful place. Wonderful owner and staff. Our stay there was a total delight., by James

8. Lakehouse Inn

A neatly made bed in a room with a wooden floor, a bedside table with a lamp, and a wall-mounted thermostat.

Location: Lee
Guest rating: 9.6/10 (Exceptional, 303 reviews)
Review: Staff wonderful, homemade breakfasts, outstanding experience!, by Kathleen

9. The Inn at Stockbridge

Location: Stockbridge
Guest rating: 9.6/10 (Exceptional, 110 reviews)
Price: $229 nightly, $256 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum., by Kimberly

10. 9 Academy

A white building with a number '9' sign, a covered entrance, and six planters with shrubs.

Location: Salisbury
Guest rating: 9.4/10 (Exceptional, 15 reviews)
Price: $534 nightly, $615 total, Dec 16 - Dec 17, Total with taxes and fees, for Our top choices for Sheffield 4-star hotels
Review: Incredible space. I plan on staying again anytime I’m in the area. Wonderful staff, very easy check in and check out. Excellent room and amenities., by Kyle

11. Rock Hall Luxe Lodging

A swimming pool with clear water, surrounded by lush greenery and yellow flowers.

Location: Winsted
Guest rating: 10/10 (Exceptional, 4 reviews)
Review: 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., by Jessica

Top Sheffield Hotel Reviews

The White Hart

Address: 15 Under Mountain Rd, Salisbury, CT, 06068, US
Location: Salisbury
Star rating: 4/5
Guest rating: 9.8/10 (156 reviews)
Review: We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our..., by thomas, August 29, 2021, rated 10/10 Excellent

The Old Inn On The Green

Address: 134 Hartsville-New Marlborough Rd, Great Barrington, MA, 01230, US
Location: Great Barrington
Star rating: 4/5
Guest rating: 9.2/10 (96 reviews)
Review: Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable., by Rishi, October 11, 2022, rated 10/10 Excellent

The Inn at Stockbridge

Address: 30 East Street, Stockbridge, MA, 01262, US
Location: Stockbridge
Star rating: 4/5
Guest rating: 9.6/10 (110 reviews)
Review: Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌, by Kevin, February 19, 2024, rated 10/10 Excellent

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

Address: 26 Glendale Road, RR 183, Stockbridge, MA, 01262, US
Location: Stockbridge
Star rating: 4.5/5
Guest rating: 9.4/10 (121 reviews)
Review: Diane is an absolutely lovely host--and breakfast at their table is a great experience., by Charles, January 2, 2020, rated 10/10 Excellent

Devonfield Inn B&B

Address: 85 Stockbridge Rd., Lee, MA, 01238, US
Location: Lee
Star rating: 4/5
Guest rating: 10/10 (141 reviews)
Review: The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!, by Anonymous traveler, January 20, 2019, rated 10/10 Excellent

9 Academy

Address: 9 Academy St, Salisbury, CT, 06068, US
Location: Salisbury
Star rating: 4/5
Guest rating: 9.4/10 (15 reviews)
Review: Incredible space. I plan on staying again anytime I’m in the area. Wonderful staff, very easy check in and check out. Excellent room and amenities., by Kyle, September 22, 2026, rated 10/10 Excellent

Garden Gables

A modern bedroom with a four-poster bed, a fireplace, and a large floral mural on the wall.

Location: Lenox
Review: Awesome ropes!, by Kyle, November 2, 2026, rated 10/10 Excellent

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 $209

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.

Are there any 4-star casino hotels in Sheffield?

Shuffle between your room and the craps table with ease by using our filters to find 4-star casino hotels in and around Sheffield. Celebrating with somebody special? Refine your search further by choosing amenities with a wow-factor, like a view or pool.