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Find Business Hotels in Stockbridge, MA

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Our top choices for Stockbridge business-friendly hotels

Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
$179 nightly
The price is $200
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Red Lion Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$94 nightly
The price is $105
Jan 4 - Jan 5, 2026
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 21 - Dec 22
Total with taxes and fees
Element Lenox Berkshires
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, (1000)
"Great stay there!! Very friendly staff"
United States
Ann
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
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, (707)
"Great hospitality "
United States
regina maria
$107 nightly
The price is $120
Dec 17 - Dec 18
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$93 nightly
The price is $104
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1002)
"Clean room, nice location "
United States
Devron
$76 nightly
The price is $85
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn Great Barrington
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Check-in/check-out kiosk
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (787)
"This place is so peaceful and the staff is always helpful "
United States
Leona
$108 nightly
The price is $120
Jan 11 - Jan 12, 2026
Total with taxes and fees
Berkshire Mountain Lodge
Exterior
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
$135 nightly
The price is $151
Dec 16 - Dec 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington 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.
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Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

How much do business-friendly hotels in Stockbridge cost?
You'll pay between $84 and $200 per night for business-friendly hotels in Stockbridge. Epic deals on stays that cater to work-related travelers are a few clicks 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 Stockbridge?
Stockbridge has multiple business-friendly hotels with a total average guest review rating of 8.8. One of the most popular is Courtyard by Marriott Lenox Berkshires. Put your laptop bag down and relax at this 3-stars option, which includes a cafe and a firepit. Corporate travelers also recommend Hampton Inn & Suites Berkshires-Lenox. It has a 2.5-stars rating and amenities such as pool sun loungers and a swimming pool.
How many business-friendly hotels are there in Stockbridge?
When work takes you to Stockbridge, there are 3 business-friendly hotels to select from. These stays combine a well-suited location with the amenities corporate travelers need.
What are the best cheap business-friendly hotels in Stockbridge?
Cut costs on your next work trip to Stockbridge by choosing one of our business-friendly hotels that start at $84 per night. One low-priced property is Hampton Inn & Suites Berkshires-Lenox, which comes with amenities like pool sun loungers and a swimming pool. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is another popular pick for corporate travelers with a tight budget. It offers a swimming pool and a picnic area. Your Stockbridge visit shouldn't be all work and no play, though. Get out and discover some fun and free attractions, such as Lake Mansfield Park and Furnace Brook Winery at Hilltop Orchards. 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 in Stockbridge that are also business friendly?
Taking a trip with the fam, and staying in contact with colleagues, is a snap at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires. Make use of amenities like complimentary breakfast and a playground at this favorite 2.5-stars retreat in Stockbridge. Another great option is Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires, an IHG Hotel. Get down to business and then enjoy quality time with your loved ones at this 3.5-stars property. A playground and miniature golf are just two of its many conveniences. Once you've gotten work out of the way, there are plenty of family-friendly attractions to visit around Stockbridge. Pleasant Valley Wilderness Sanctuary and Berkshire Scenic Railway Museum promise fun for all ages.
Why book your business-friendly hotel in Stockbridge with Expedia?
With conveniences like conference rooms, housekeeping and free WiFi, our business-friendly hotels come with everything you'll need to close your important deal — and then kick back! Enter your travel destination and preferred dates and we'll help you plan everything else.
How can I find cheap business-friendly hotels in Stockbridge?
When you're traveling for work in Stockbridge, our "business friendly" filter will help you find the perfect hotel. From dependable WiFi to workspaces and meeting rooms, they have the amenities you need to get the job done. Another tip? Narrow your search by your preferred star rating and budget to see the cheapest accommodations.
What is there to do in Stockbridge near my business-friendly hotel?
Whatever you're into, Stockbridge has plenty to keep you on the move. Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area are on many travelers' trip plans. Don't leave without exploring October Mountain State Forest, Mahaiwe Performing Arts Center and Shakespeare and Company either. With Expedia's business-friendly hotel deals, you'll be able to see even more awesome attractions like these with the cash you save.

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