Photo by Photo courtesy of Berkshire Visitors Bureau

Hotels with Restaurants in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Restaurants

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for The Berkshires hotels with a restaurant

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1003)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is P5,181
P5,788 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (821)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is P7,440
P8,311 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Berkshires Untold
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is P8,753
P12,402 total
includes taxes & fees
Jan 26 - Jan 27, 2026
The Red Lion Inn
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is P7,513
P8,392 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Lenox Pittsfield
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (594)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is P8,166
P9,121 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Courtyard by Marriott Lenox Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is P7,931
P8,859 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1001)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is P6,100
P6,814 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is P8,416
P9,683 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Cornell Inn, Lenox & The Berkshires
Front of property - evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (555)
"staff was great"
United States
Tim
The price is P12,866
P14,371 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Williams Inn
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (17)
"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
The price is P21,942
P26,478 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Prospect 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.
View all properties

Top The Berkshires Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Staff were very friendly and flexible. The rooms were comfortable, spacious and clean. Easy checking and checking out. Plenty of parking. Would definitely stay there again and again. "
Robert 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

How much do hotels with dining in The Berkshires cost?
You can expect to pay between P5,788 and P26,478 per night for hotels in The Berkshires. A perfect stay with a restaurant, or one with access to a top foodie area, is just 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 The Berkshires?
Get ready to experience the culinary delights of The Berkshires when you stay at one of our multiple hotels with restaurants or in foodie areas. With a total average guest review rating of 9.1, there's an irresistible option for every budget and taste. If your travels include a stop in Lenox, check out Hotel On North, a 3.5-star escape with mountain views and a restaurant. Another traveler favorite here is Hilton Garden Inn Lenox Pittsfield. This 3-star stay has a terrace and a swimming pool.
How many hotels with dining are there in The Berkshires?
Take a look at our 97 hotels with dining in The Berkshires and then select your favorite. Whether you're off on a vacation with the family or kicking it with your pals, your perfect stay is just clicks away.
What are the best cheap hotels with dining in The Berkshires?
With hotels with dining starting at P5,788 per night, you'll have extra money in your pocket for exploring The Berkshires's cuisine. If Lenox is where you want to be, take a look at Hampton Inn & Suites Berkshires-Lenox. Mountain views and a swimming pool help make this stay a top choice. Expedia also has low-cost hotels with dining in Williamstown. Get comfy at Berkshire Valley Inn and make use of amenities such as mountain views and WiFi. There are lots of free and exciting things to do wherever you choose to go in The Berkshires. If you're traveling to Lenox, explore Canoe Meadows Wildlife Sanctuary. You can also sightsee without spending a dime in Williamstown. Mount Greylock is a popular free thing to do here. 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.
Are there any family-friendly hotels with dining in The Berkshires?
You'll discover some excellent family-friendly hotels with dining in The Berkshires. If you're traveling to Lenox, experience the gastronomic delights of the city from Hotel On North. Amenities at this 3.5-star hotel include WiFi and housekeeping services. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires, an IHG Hotel is another top choice for families looking for hotels with restaurants or near foodie areas. This 3.5-star option features miniature golf and a playground and is also in Lenox. Once you've settled into your room and sampled some of the local food and drink, get out and discover Lenox. Enjoy memorable moments together at family-friendly attractions such as Hancock Shaker Village and Berkshire Museum.
Are there any 5-star hotels with dining in The Berkshires?
While there aren't any 5-star hotels with dining in The Berkshires, there are still stylish options to choose from. Lenox on your must-visit list? Garden Gables Inn is a 4-star retreat that will put you close to some top-notch foodie experiences. Designer toiletries and treatment rooms are among the amenities here. Hampton Terrace Inn is another choice with dining in Lenox. Also rated 4 stars and featuring a terrace and a swimming pool, there's plenty to love about this hotel.
Why book your hotel with dining in The Berkshires with Expedia?
Whether you're after a hotel with a restaurant, or one that's near a foodie enclave, Expedia will have a stay that fits your tastes. Use our filters to search for The Berkshires hotels with on-site dining. You can also look up properties in popular locations filled with restaurants, markets or cafés. Whatever suits your style, you'll always get a tasty bargain with Expedia!
How can I find cheap hotels with dining in The Berkshires?
Expedia can help you track down cheap hotels with dining in The Berkshires. Use our filter tools to find properties with restaurants or delightful extras, such as included lunch and dinner. You can also choose how much you want to spend per night and your preferred hotel star rating to save money.
What is there to do in The Berkshires near my hotel with dining?
The best accessory to take on your The Berkshires escape is an awesome itinerary! Sterling and Francine Clark Art Institute, Williams College Museum of Art and Hopkins Observatory are some of the most popular things to do if you're staying in Williamstown. Pittsfield also lures visitors with its big-name attractions, such as Bousquet Ski Area. In the mood to explore more? Drop by Barrington Stage Company and Berkshire Museum too.

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