Find Hotels with Restaurants in Pittsfield, MA

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Check availability on Pittsfield Hotels with Restaurants

Tonight
Dec 23 - Dec 24
Tomorrow
Dec 24 - Dec 25
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Pittsfield hotels with a restaurant

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$98 nightly
The price is $109
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
$128 nightly
The price is $143
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
$135 nightly
The price is $151
Jan 4 - Jan 5, 2026
Total with taxes and fees
Element Lenox Berkshires
Exterior
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
$75 nightly
The price is $84
Jan 19 - Jan 20, 2026
Total with taxes and fees
Cozy Corner Motel
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$100 nightly
The price is $112
Jan 13 - Jan 14, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1003)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
$83 nightly
The price is $92
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Lee - Lenox South
Pool
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (899)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
$83 nightly
The price is $93
Dec 25 - Dec 26
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (996)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
$85 nightly
The price is $95
Dec 25 - Dec 26
Total with taxes and fees
Willows Motel Williamstown
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
$178 nightly
The price is $199
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Red Lion Inn
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
$139 nightly
The price is $155
Jan 6 - Jan 7, 2026
Total with taxes and fees
Courtyard 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 Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
Brandon 3-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

How much do hotels with dining in Pittsfield cost?
The rate for hotels in Pittsfield ranges from $84 to $199 per night. Expedia has tempting deals on properties with restaurants or close to top food areas that'll please both your taste buds and wallet. 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 Pittsfield?
We recommend Hotel On North. Cozy up at this 3.5-star stay which features mountain views and front desk services. Hilton Garden Inn Lenox Pittsfield is another popular hotel with dining worth considering. Book into this 3-star option and make the most of conveniences such as an electric car charging station and a terrace. You'll have your pick of multiple hotels with dining in Pittsfield with a total average guest review rating of 8.6.
How many hotels with dining are there in Pittsfield?
Pack your bags and choose from 9 hotels with dining in Pittsfield. For a business trip, a solo adventure and everything in between, Expedia is here to help you find a stay to satisfy your inner foodie in a few quick clicks.
What are the best cheap hotels with dining in Pittsfield?
Use Hampton Inn & Suites Berkshires-Lenox as a base to eat your way around the food scene of Pittsfield. This affordable getaway comes with amenities such as a swimming pool and pool sun loungers. Another excellent choice that'll satisfy both your budget and appetite is The Yankee, Trademark Collection by Wyndham. Conveniences here include pool sun loungers and mountain views. Hotels with dining in Pittsfield start from just $84 per night. If you're exploring Pittsfield and want to save money, there are loads of free and popular attractions to add to your to-do list. Wahconah Falls State Park and Canoe Meadows Wildlife Sanctuary are always favorites. 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 Pittsfield?
Take the crew to Hotel On North, a 3.5-star option just a short drive from town. Conveniences here include WiFi and room service. Another family-friendly hotel with dining in Pittsfield is The Black Swan Lee - Lenox, Ascend Hotel Collection. Complimentary breakfast and a picnic area help make this 3-star escape a favorite. Pittsfield boasts plenty of family-friendly attractions to explore when you need to keep the kids busy. Hancock Shaker Village and Berkshire Museum promise a fun day out for everyone.
Are there any 5-star hotels with dining in Pittsfield?
While 5-star options are in short supply, there are 4-star hotels that offer access to terrific dining experiences in Pittsfield. Consider booking Garden Gables Inn, about 6 miles from downtown. Pillow top mattresses and a terrace are just a couple of the conveniences you'll enjoy here. Hampton Terrace Inn is another upscale option that foodies will enjoy. This property is located around 7 miles from the center of Pittsfield and offers top amenities like a tennis court and a swimming pool.
Why book your hotel with dining in Pittsfield with Expedia?
With Expedia, it's easy to find your dream hotel with dining in Pittsfield. Make your way to the filters to search for stays with an on-site restaurant. If you need to stick to a budget, select how much you'd like to spend and the preferred star rating of your hotel. We'll help you find the right stay whatever your bank balance or tastes.
How can I find cheap hotels with dining in Pittsfield?
Expedia can help you easily source cheap hotels with dining in Pittsfield. Simply use our handy filter tools to lock in stays with restaurants or tasty 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 cut costs.
What is there to do in Pittsfield near my hotel with dining?
No matter your tastes or interests, Pittsfield has plenty of things to keep you going. Bousquet Ski Area, Pittsfield State Forest and Barrington Stage Company are on many visitors' itineraries. You shouldn't miss Berkshire Museum, Colonial Theater and Arrowhead Museum either. With Expedia's hotel deals in Pittsfield, you'll be able to see even more terrific attractions like these with the money you save.

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