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Find All-inclusive Resorts in The Berkshires, MA

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Top The Berkshires All-inclusive Resorts

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

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
$85 nightly
The price is $95
Dec 8 - Dec 9
Total with taxes and fees
Willows Motel Williamstown

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
$99 nightly
The price is $111
Dec 8 - Dec 9
Total with taxes and fees
Maple Terrace Motel

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

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
$190 nightly
The price is $213
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Red Lion Inn

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
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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

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
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

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.
$67 nightly
The price is $74
Dec 8 - Dec 9
Total with taxes and fees
Monument Mountain Motel

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
$186 nightly
The price is $208
Dec 9 - Dec 10
Total with taxes and fees
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.

Find out more about The Berkshires

Discover top The Berkshires attractions

The Berkshires offers an enticing blend of natural beauty and cultural richness, perfect for travelers seeking all-inclusive hotels. Start your day at the renowned Norman Rockwell Museum, where you can immerse yourself in the heartwarming art of America's favorite illustrator. Follow it up with a visit to Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy outdoor concerts in a breathtaking setting. Families will love the Berkshire Museum, which combines art, history, and science, offering interactive exhibits that engage children and adults alike. For outdoor enthusiasts, a hike through the picturesque Mount Greylock State Reservation provides stunning panoramic views, while the nearby Jiminy Peak offers year-round recreational activities, from skiing in winter to mountain biking in summer. When it comes to all-inclusive stays, expect gourmet dining options that showcase local flavors, such as farm-to-table meals featuring fresh produce from the area. Many resorts also include activities like guided hikes, art classes, or spa treatments, ensuring every member of the family is catered for. The Lenox area, in particular, is perfect for an all-inclusive experience, allowing guests to explore charming shops, enjoy fine dining, and take in the artistic vibe of the region while being pampered in luxurious accommodations. With attentive guest service and a range of amenities, your stay will feel both indulgent and rejuvenating.

Top The Berkshires Hotel Reviews

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