Find Hotels with Restaurants in Sheffield, MA

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Check availability on Sheffield Hotels with Restaurants

Our top choices for Sheffield hotels with a restaurant

Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 16 - Dec 17
Total with taxes and fees
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1006)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$101 nightly
The price is $113
Dec 21 - Dec 22
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1001)
"Staff was very helpful - easy location - clean rooms!"
United States
Karen
$91 nightly
The price is $101
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$183 nightly
The price is $205
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Red Lion Inn
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (811)
"Easiest check in and out. Great food in dining room. "
United States
William
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
Berkshires Untold
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$250 nightly
The price is $280
Dec 10 - Dec 11
Total with taxes and fees
Prospect Berkshires
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (187)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
$140 nightly
The price is $157
Dec 10 - Dec 11
Total with taxes and fees
the Alander
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
$169 nightly
The price is $189
Dec 10 - Dec 11
Total with taxes and fees
Little Cat Lodge
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (589)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
$135 nightly
The price is $151
Dec 14 - Dec 15
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
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.
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Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

How much do hotels with dining in Sheffield cost?
You'll pay between $101 and $280 per night for hotels in Sheffield. The perfect stay with a restaurant, or one that's close to epic foodie experiences, is only a few clicks away with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with dining in Sheffield?
Sheffield has multiple hotels with dining with a total average guest review rating of 9.1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a popular option if you'd like to sink your teeth into the local dining scene. It has a 2.5-star rating and offers amenities such as a swimming pool and blackout curtains. Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel is another guest favorite. This 2.5-star hotel offers access to some delightful food experiences and comes with pillow top mattresses and a nearby river.
How many hotels with dining are there in Sheffield?
Sheffield has 1 hotels within reach of some great dining options. To help you find the ideal digs, use our filters to search for other must-have amenities or perks.
What are the best cheap hotels with dining in Sheffield?
Keep both your budget and taste buds happy at one of our Sheffield hotels with dining that start at just $101 per night. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires will give you easy access to some mouthwatering culinary experiences. Useful amenities here include a swimming pool and a picnic area. Also take a look at Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel, which offers a nearby river and a swimming pool. Use the money you save at either stay to eat your way around Sheffield! Seeing free attractions in Sheffield will stretch your vacation budget even further. Bash Bish Falls State Park and Lake Mansfield Park are tourist favorites. With the money you save, you can check out the local food scene. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the top motels with dining in Sheffield?
The Briarcliff Motel is a sought-after choice, located around 9 mi north of downtown Sheffield. With a garden and free WiFi, this motel with dining is an excellent place to kick back and relax after exploring the local culinary scene.When you're ready to lace up your comfy shoes and go sightseeing, make your way straight to Magnolia Bluffs Casino. Ashley House is another popular attraction in Sheffield.
Are there any family-friendly hotels with dining in Sheffield?
Check in to Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires and eat your way around Sheffield. This family-friendly hotel with dining has a 2.5-star rating and features including complimentary breakfast and a playground. After checking in and chilling in your comfy new digs, it's time to discover some of the local sights. Umpachene Falls Park and Bash Bish Falls State Park are among the family-friendly attractions in Sheffield.
Why book your hotel with dining in Sheffield with Expedia?
Whether you're looking for a hotel with a restaurant, or one that's close to a foodie hub, Expedia will have an escape that's to your tastes. Use our filters to search for Sheffield hotels with on-site dining. You can also search for properties in desired locations filled with restaurants, markets or cafés. Whatever you opt for, you'll always pick up a tasty deal with Expedia!
How can I find cheap hotels with dining in Sheffield?
The simplest way to score cheap hotels with dining in Sheffield is with Expedia's user-friendly filter tool. Reserve stays with restaurants or tasty extra touches, like included breakfast, lunch and dinner. You can also narrow down your search results by amenities, budget and star rating to discover awesome prices in just a few keystrokes.
What is there to do in Sheffield near my hotel with dining?
Once you've unpacked your suitcases, set out and discover the awesome things Sheffield has to offer. Magnolia Bluffs Casino is a great attraction to add to your to-do list.

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