Photo by Photo courtesy of Berkshire Visitors Bureau

The Berkshires Hotel Guide - Business Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Business Hotels

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

Our top choices for The Berkshires business-friendly hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is €88
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
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
The price is €93
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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
The price is €132
includes taxes & fees
20 Jan - 21 Jan 2026
Courtyard by Marriott Lenox Berkshires
Front of property – evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (808)
"Clean room and staff was super friendly"
United States
Yuen
The price is €141
includes taxes & fees
1 Jan - 2 Jan 2026
Hotel On North
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is €112
includes taxes & fees
13 Jan - 14 Jan 2026
Berkshire Mountain Lodge
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is €116
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is €128
includes taxes & fees
19 Jan - 20 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Outdoor pool, pool 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
The price is €180
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is €72
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (710)
"Great hospitality "
United States
regina maria
The price is €102
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

How much do business-friendly hotels in The Berkshires cost?
Expect to pay between €72 and €180 per night for business-friendly hotels in The Berkshires. Epic deals on stays that cater to corporate travellers are only a click away on 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 business-friendly hotels in The Berkshires?
There are multiple business-friendly hotels in The Berkshires with a total average guest review rating of 8.8, so you're sure to discover a place that suits your needs. On your way to Lenox? Hotel On North is highly rated by corporate travellers. This 3.5-stars option offers conveniences like mountain views and a restaurant. Courtyard by Marriott Lenox Berkshires also gets top marks from business guests. Take advantage of an electric car charging station and a cafe at this 3-stars escape in Lenox.
How many business-friendly hotels are there in The Berkshires?
When work takes you travelling throughout The Berkshires, you'll have 59 business-friendly hotels to select from.
What are the best cheap business-friendly hotels in The Berkshires?
When you're on the road for work in The Berkshires, Expedia will help you find the right business-friendly hotel. Hampton Inn & Suites Berkshires-Lenox is a top budget option in Lenox. Pool sun loungers and a swimming pool are some of its many amenities. Seeking affordable stays in Williamstown? Fairfield Inn & Suites by Marriott Williamstown is rated highly with corporate guests. It has conveniences that make it easy to both work and play, including mountain views and a swimming pool. Business-friendly hotels in The Berkshires start at only €72 a night. Want to explore The Berkshires without blowing your budget? Take a break from your work events to visit awesome free attractions such as Canoe Meadows Wildlife Sanctuary in Lenox. Williamstown also has plenty of things to do that don't cost anything, including Mount Greylock. 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.
What are the top business-friendly motels in The Berkshires?
If your The Berkshires trip includes Williamstown, consider Cosy Corner Motel. Approximately 3 kilometres north of the downtown area and offering a lazy river and a garden, it's popular with corporate guests. Alternatively, work comfortably from Northside Motel. A garden and a barbecue grill are among the conveniences at this stay, which is located around 0.64 kilometres northwest of central Williamstown.There are all kinds of things to keep you entertained when you've got some free time in Lenox. Norman Rockwell Museum and Bousquet Ski Area are worth adding to your itinerary.
Are there any family-friendly hotels in The Berkshires that are also business friendly?
Certainly. You'll find some excellent family-friendly hotels that are also business friendly in The Berkshires. If you're on your way to Lenox, check out Holiday Inn Club Holidays Oak n' Spruce Resort in the Berkshires, an IHG Hotel. It comes with useful amenities like a playground and miniature golf and has a 3.5-stars rating. Alternatively, consider The Black Swan Lee - Lenox, Ascend Hotel Collection. This 3-stars stay in Lenox is perfect for both business and leisure travellers and offers complimentary breakfast, laundry facilities and more. Once you've gotten work out of the way, get out and discover Lenox with the kids. Popular family-friendly attractions include Hancock Shaker Village and Berkshire Museum.
Why book your business-friendly hotel in The Berkshires with Expedia?
With handy amenities like meeting rooms, housekeeping and free parking, our business-friendly accommodation come with all you'll need to get the job done — and then relax in the comfort of your room. Enter your travel destination and preferred dates and Expedia will help you organise the rest.
How can I find cheap business-friendly hotels in The Berkshires?
Expedia can help you search for cheap business-friendly hotels in The Berkshires. Simply head to our "traveller experience" filter and click on "business friendly." This will show you stays with amenities designed to help you work and rest comfortably, like free WiFi and included breakfast. You can also choose your budget and preferred star rating to keep costs down.
What is there to do in The Berkshires near my business-friendly hotel?
The most important travel accessory for your The Berkshires business journey is a fabulous itinerary for when you're not in meetings! Shakespeare and Company, Pleasant Valley Wilderness Sanctuary and Tanglewood Music Centre are some of the well-known sights if you're headed to Lenox. Williamstown also has plenty of famous attractions, such as Sterling and Francine Clark Art Institute, Williams College Museum of Art and Williamstown Historical Museum.

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