Hotels with Restaurants in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Restaurants

Tonight
Jul 6 - Jul 7
Tomorrow
Jul 7 - Jul 8
Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20

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, (1001)
"I had excellent stay at the Red Lion Inn "
The price is P12,357
P16,324 total
includes taxes & fees
Aug 4 - Aug 5
The Red Lion Inn
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (625)
"Great place stay after an evening at Tanglewood!"
The price is P22,294
P24,902 total
includes taxes & fees
Jul 11 - Jul 12
Berkshires Untold
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (460)
"Wonderful stay. Helpful, professional staff. "
The price is P13,949
P15,580 total
includes taxes & fees
Jul 9 - Jul 10
The Williams Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (813)
"Clean rooms Staff was very friendly and helpful "
The price is P6,940
P7,752 total
includes taxes & fees
Jul 13 - Jul 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1004)
"Friendly staff, easy parking"
The price is P6,667
P7,447 total
includes taxes & fees
Jul 21 - Jul 22
Quality Inn
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, (1002)
"Great place"
The price is P10,024
P11,197 total
includes taxes & fees
Jul 13 - Jul 14
The Black Swan Lee - Lenox, Ascend Hotel Collection
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (559)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is P11,962
P13,362 total
includes taxes & fees
Jul 13 - Jul 14
Courtyard by Marriott Lenox Berkshires
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, (1001)
"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 P8,468
P11,665 total
includes taxes & fees
Jul 21 - Jul 22
The Cornell Inn, Lenox & The Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (946)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
The price is P10,100
P11,282 total
includes taxes & fees
Jul 7 - Jul 8
Jiminy Peak Mountain Resort
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (636)
"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 P12,677
P14,160 total
includes taxes & fees
Jul 13 - Jul 14
Hilton Garden Inn Lenox Pittsfield
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.

Frequently asked questions

How much do hotels with dining in The Berkshires cost?
You can expect to pay between P6,667 and P22,294 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 8.8, 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 P6,667 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.