Hotels with Restaurants in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Restaurants

Tonight
Jul 29 - Jul 30
Tomorrow
Jul 30 - Jul 31
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top The Berkshires Hotels with Restaurants

The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1011)
"I had excellent stay at the Red Lion Inn "
The price is P11,035
P14,881 total
includes taxes & fees
Aug 25 - Aug 26
The Red Lion Inn
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is P11,607
P12,965 total
includes taxes & fees
Aug 24 - Aug 25
Courtyard by Marriott Lenox Berkshires
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (650)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is P20,515
P22,916 total
includes taxes & fees
Aug 15 - Aug 16
Berkshires Untold
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is P7,621
P10,748 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (838)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is P7,370
P8,232 total
includes taxes & fees
Jul 31 - Aug 1
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (475)
"Wonderful stay. Helpful, professional staff. "
The price is P14,345
P16,024 total
includes taxes & fees
Aug 11 - Aug 12
The Williams Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1009)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is P7,135
P7,969 total
includes taxes & fees
Aug 26 - Aug 27
Quality Inn
Hilton Garden Inn Lenox Pittsfield
Exterior

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P11,771
P13,148 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Lenox Pittsfield
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1007)
"Beautiful location!"
The price is P11,130
P12,432 total
includes taxes & fees
Aug 6 - Aug 7
The Black Swan Lee - Lenox, Ascend Hotel Collection
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.

Top The Berkshires Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"This hotel was exactly what we needed after a busy day. Highly recommend the king suites for families with multiple kids. Accomdated our crew comfortably. Staff could not have been nicer. "
Elizabeth 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites

Frequently asked questions

How much do hotels with dining in The Berkshires cost?
You can expect to pay between P7,370 and P11,130 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 8.6, 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 P7,370 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.