A person snowboarding down a snowy slope.

Hotels with Restaurants 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 Hotels with Restaurants

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for The Berkshires hotels with a restaurant

Lobby lounge

1. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,014 reviews)
"Clean and modern hotel close to the center part of Lenox."
United States
Ivana
The price is P8,908
P9,950 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold
Lobby

2. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,006 reviews)
"great location very clean friendly staff"
United States
Jeanne
The price is P6,206
P6,932 total
includes taxes & fees
Aug 31 - Sep 1
Quality Inn Lee - Lenox South
Property grounds

3. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,009 reviews)
"I always enjoy the Red Lion inn."
United States
Merideth
The price is P10,640
P14,904 total
includes taxes & fees
Aug 23 - Aug 24
The Red Lion Inn
Exterior

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is P10,807
P12,433 total
includes taxes & fees
Aug 26 - Aug 27
The Cornell Inn, Lenox & The Berkshires
Lake

5. 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, (1,003 reviews)
"enjoyable stay"
United States
James
The price is P12,410
P13,863 total
includes taxes & fees
Aug 9 - Aug 10
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,010 reviews)
"Lots of construction going on, but the staff was great. They valet-parked my car and had it waiting for me in the morning. The room was clean and comfortable."
United States
David
The price is P7,717
P8,620 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

7. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.8 out of 10, Exceptional, (116 reviews)
"Absolutely loved our stay. The staff were warm and welcoming, the lodge is so cute & well put together, & the restaurant is delicious. We will definitely be back!"
United States
Jolie
The price is P13,398
P15,006 total
includes taxes & fees
Aug 10 - Aug 11
Little Cat Lodge
Gazebo

8. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (936 reviews)
"Loved this place"
United States
Jeremy
The price is P5,742
P6,738 total
includes taxes & fees
Aug 9 - Aug 10
Cozy Corner Motel
Property amenity

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (644 reviews)
"Helpful staff, clean room and great facilities."
United Kingdom
Laura
The price is P12,950
P14,465 total
includes taxes & fees
Aug 19 - Aug 20
Courtyard by Marriott Lenox Berkshires
Lobby

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (32 reviews)
"Great staff very friendly rooms very clezn"
United States
Lawrence
The price is P12,881
P14,388 total
includes taxes & fees
Aug 23 - Aug 24
Element 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.
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Place is generally good but there were few significant problems. The main problem is absence of any food place, stores or restaurants on the proximity of the property. Another problem is a mediocre soundproof. The rest was good. Convenient bed, full kitchen, balcony."
Inna 3-night trip
Posted 9 hours ago
Vacation Village in the Berkshires

Frequently asked questions

How much do hotels with dining in The Berkshires cost?
You can expect to pay between P6,738 and P15,006 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 P6,738 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.

Explore a world of travel with Expedia