Photo by Photo courtesy of Berkshire Visitors Bureau

Hotels with shuttle in The Berkshires, Massachusetts

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Check prices for these dates

Our top choices for The Berkshires hotels with transportation

1. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
"Lovely place!"
United States
Eyee
The price is P8,229
P13,766 total
includes taxes & fees
Dec 8 - Dec 9
Garden Gables

2. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The location was good for our trip."
United States
Basil
The price is P8,007
P8,944 total
includes taxes & fees
Nov 20 - Nov 21
The Yankee Inn

3. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is P7,320
P8,176 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is P6,748
P7,537 total
includes taxes & fees
Dec 3 - Dec 4
The Black Swan Lee - Lenox, an Ascend Collection Hotel

5. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,067 reviews)
"Very nice place beautiful view"
United States
Brian
The price is P6,630
P7,405 total
includes taxes & fees
Nov 17 - Nov 18
Berkshires Untold

6. 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, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is P5,229
P5,841 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Express Hotel & Suites Great Barrington by IHG

7. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (688 reviews)
"Great stay!"
United States
Vandhana
The price is P7,919
P8,846 total
includes taxes & fees
Nov 15 - Nov 16
Courtyard by Marriott Lenox Berkshires

8. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is P6,489
P7,248 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

9. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,002 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is P10,711
P12,286 total
includes taxes & fees
Nov 10 - Nov 11
The Cornell Inn, Lenox & The Berkshires

10. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is P4,766
P5,324 total
includes taxes & fees
Dec 3 - Dec 4
Quality Inn Great Barrington
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.