The Berkshires Hotels with Restaurant, Massachusetts: The Berkshires Hotel Guide

A person snowboarding down a snowy slope.

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 Restaurant

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for The Berkshires hotels with a restaurant

1. Berkshires Untold

Lenox

Ivana

€127

includes taxes & fees

10 Sept - 11 Sept

2. The Red Lion Inn

Stockbridge

Merideth

€196

includes taxes & fees

9 Sept - 10 Sept

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

James

€130

includes taxes & fees

7 Sept - 8 Sept

4. Quality Inn Lee - Lenox South

Lee

Christine

€104

includes taxes & fees

31 Aug - 1 Sept

5. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

€177

includes taxes & fees

25 Aug - 26 Aug

6. Cozy Corner Motel

Williamstown

Jeremy

€90

includes taxes & fees

9 Sept - 10 Sept

7. Courtyard by Marriott Lenox Berkshires

Lenox

Laura

€180

includes taxes & fees

19 Aug - 20 Aug

8. the Alander

Copake

Jerry

€136

includes taxes & fees

12 Aug - 13 Aug

View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

8/10 Good

"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."

The Red Lion Inn

10/10 Excellent

"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."

The Yankee Inn

8/10 Good

"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."

Jiminy Peak Mountain Resort

10/10 Excellent

"Quiet and serene. Great weekend escape!"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Room was very small and room rate was big!"

The Little Lion

10/10 Excellent

"Great location. Functional and affordable. Pet friendly."

Howard Johnson by Wyndham Lenox

10/10 Excellent

"Parking"

FairBridge Inn Express

10/10 Excellent

"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."

Frequently asked questions

How much do hotels with dining in The Berkshires cost?

You can expect to pay between €90 and €205 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 traveller favourite here is Hilton Garden Inn Lenox Pittsfield. This 3-star stay has a terrace and a swimming pool.

How many hotels with restaurants are there in The Berkshires?

Take a look at our 97 hotels with restaurants in The Berkshires and then select your favourite. Whether you're off on a holiday 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 €90 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 travelling 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 travelling 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 Holidays 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 restaurants 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 restaurants in The Berkshires?

Expedia can help you track down cheap hotels with restaurants 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 restaurants?

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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on The Berkshires Hotels with Restaurant

Our top choices for The Berkshires hotels with a restaurant

1. Berkshires Untold

2. The Red Lion Inn

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

4. Quality Inn Lee - Lenox South

5. The Cornell Inn, Lenox & The Berkshires

6. Cozy Corner Motel

7. Courtyard by Marriott Lenox Berkshires

8. the Alander

9. Hilton Garden Inn Lenox Pittsfield

10. Element by Marriott Lenox Berkshires

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

The Red Lion Inn

The Yankee Inn

Jiminy Peak Mountain Resort

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Cornell Inn, Lenox & The Berkshires

The Little Lion

Howard Johnson by Wyndham Lenox

FairBridge Inn Express

Frequently asked questions

Explore a world of travel with Expedia

The Berkshires Hotel Guide - Hotels with Restaurant in The Berkshires, Massachusetts

Change your mind

Treat yourself

Be picky

Check availability on The Berkshires Hotels with Restaurant

Our top choices for The Berkshires hotels with a restaurant

1. Berkshires Untold

2. The Red Lion Inn

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

4. Quality Inn Lee - Lenox South

5. The Cornell Inn, Lenox & The Berkshires

6. Cozy Corner Motel

7. Courtyard by Marriott Lenox Berkshires

8. the Alander

9. Hilton Garden Inn Lenox Pittsfield

10. Element by Marriott Lenox Berkshires

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

The Red Lion Inn

The Yankee Inn

Jiminy Peak Mountain Resort

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Cornell Inn, Lenox & The Berkshires

The Little Lion

Howard Johnson by Wyndham Lenox

FairBridge Inn Express

Frequently asked questions

Explore a world of travel with Expedia