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All Inclusive Resorts in The Berkshires, Massachusetts

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Check availability on The Berkshires All Inclusive Resorts

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Dec 7 - Dec 8
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Top The Berkshires All Inclusive Resorts

Exterior
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3.0 star property
Hancock
9.2 out of 10, Wonderful, (565)
"Good place to take your family."
United States
Maria
Club Wyndham Bentley Brook
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (992)
"Warm welcome. Great location. Best fresh fruit breakfast ever."
United States
Melissa
The price is P4,508
P5,036 total
includes taxes & fees
Dec 8 - Dec 9
Willows Motel Williamstown
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (587)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is P5,834
P6,517 total
includes taxes & fees
Dec 8 - Dec 9
Maple Terrace Motel
Exterior
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!"
United States
Ann
The price is P5,260
P5,875 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is P9,017
P12,705 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Red Lion Inn
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, (982)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is P5,410
P6,043 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
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
The price is P6,082
P6,794 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is P6,082
P6,794 total
includes taxes & fees
Dec 14 - Dec 15
Hilton Garden Inn Lenox Pittsfield
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Front of property - evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (546)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is P11,616
P12,975 total
includes taxes & fees
Dec 14 - Dec 15
The Williams Inn
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 The Berkshires Hotel Reviews

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