A person snowboarding down a snowy slope.

Hotels with Restaurants in The Berkshires

  • 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

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for The Berkshires hotels with a restaurant

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lakeside dock with kayaks and a covered boat ramp.
A lodge with a large building and a dock by a lake, surrounded by forest.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
S$165
includes taxes & fees
1 Nov - 2 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

2. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
S$180
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a fireplace, and comfortable seating.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
S$188
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
S$225
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
S$157
includes taxes & fees
27 Oct - 28 Oct
Quality Inn Lee - Lenox South
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
S$290
includes taxes & fees
1 Nov - 2 Nov
The Red Lion Inn
A building entrance with a large planter with purple flowers and a small tree.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A library with bookshelves, a television, and two armchairs.

7. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
S$160
includes taxes & fees
1 Nov - 2 Nov
Hotel On North
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
S$183
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
A spacious living area with a fireplace, wooden beams, and a large window.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

9. The Williams Inn

The Williams Inn
Williamstown
United States
Soleil
S$243
includes taxes & fees
2 Nov - 3 Nov
The Williams Inn
Room
A conference room with a whiteboard, tables, and chairs.
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

10. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
S$154
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
View all properties

Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Delightful place with charm and warmth and character. I would love to come back."
Richard 1-night trip
Posted 11 hours ago
Hotel On North
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place great price!"
James 1-night trip
Posted 20 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

8/10 Good
"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"
Theresa 2-night trip
Posted 20 hours ago
The Yankee Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."
Francesca 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 4 days ago
Quality Inn Great Barrington

Frequently asked questions

How much do hotels with dining in The Berkshires cost?
You can expect to pay between S$154 and S$290 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 9.2, 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 S$154 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.

Explore a world of travel with Expedia