Find All Inclusive Resorts and Hotels in The Berkshires, MA

  • 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 All Inclusive Resorts and Hotels

No exact matches found, but these alternatives could be just right

Recommended hotels in The Berkshires

Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (833 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is CA $152
CA $197 total
includes taxes & fees
Mar 11 - Mar 12
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is CA $126
CA $140 total
includes taxes & fees
Feb 23 - Feb 24
The Yankee, Trademark Collection by Wyndham
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (855 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is CA $120
CA $134 total
includes taxes & fees
Mar 8 - Mar 9
Berkshires Untold
Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,235 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is CA $141
CA $172 total
includes taxes & fees
Feb 12 - Feb 13
Vacation Village in the Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (600 reviews)
"Our stay was great! "
United States
Gianna
The price is CA $176
CA $197 total
includes taxes & fees
Mar 8 - Mar 9
Courtyard by Marriott Lenox Berkshires
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (823 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is CA $202
CA $226 total
includes taxes & fees
Feb 19 - Feb 20
Hotel On North
Restaurant

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, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is CA $138
CA $155 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lake

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, (1,000 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is CA $132
CA $148 total
includes taxes & fees
Mar 3 - Mar 4
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
The price is CA $226
CA $253 total
includes taxes & fees
Mar 11 - Mar 12
Hideaway Inn Lenox
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (838 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is CA $134
CA $180 total
includes taxes & fees
Feb 12 - Feb 13
Berkshire Mountain Lodge
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

Choose what matters most at all-inclusive hotels in The Berkshires

5 stars
4 stars

Top The Berkshires Hotel Reviews

Explore a world of travel with Expedia