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Showing 16-30 of 66 Resorts and Lodges

Lanesboro Country Inn

Lanesborough, Massachusetts, United States
$69

The Lanesboro Country Inn is a wonderfully intimate, centrally located cozy retreat in the heart of the Berkshires. Featuring brand new , individual log cabins, it provides spacious accommodations to help you unwind. Come relax, discover, and enjoy everything the Berkshires have to offer.... more

Williamstown Motel

Williamstown, Massachusetts, United States
$99

Located in the heart of Williamstown, in the beautiful Berkshires of Western Massachusetts, the Williamstown Motel is just minutes from Williams College, Williamstown Theater Festival, Sterling and Francine Clark Art Institute, Williams College Museum of Art, MASS MoCA in North Adams, Mount Greylock State Reservation and Jiminy Peak Ski Resort, as... more

Wyndham Vacation Resorts - Bentley Brook

Hancock, Massachusetts, United States
90
Excellent
118 Reviews
$129

See the mountainside suspended from a chairlift above Jiminy Peak Mountain and discover an unparalleled vacation destination at Wyndham Bentley Brook! This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal... more

The Williams Inn

Williamstown, Massachusetts, United States

Canyon Ranch in Lenox

Lenox, Massachusetts, United States
93
Excellent
9 Reviews
$1,130

Since 1979, Canyon Ranch has been empowering people to live healthier, longer, more joyful lives through fitness, nutrition, stress management and integrative wellness. At Canyon Ranch health resort in Lenox, located within walking distance of the lovely town of Lenox and close to upstate New York, experience the all-inclusive luxury spa vacation... more

The Village Inn

Lenox, Massachusetts, United States
$122

For over 200 years the Village Inn has offered hospitality and lodging to Berkshire travelers. With their close proximity to Tanglewood, summer home of the Boston Symphony, good music is a major part of life at the Inn. Classical recordings accompany gourmet dining, and a grand piano in the Common Room is frequently played by guests and guest... more

Berkshire Mountain Lodge

Pittsfield, Massachusetts, United States

You can find spectacular accommodations at Vacation Village properties across the country, but for a real treat head to Pittsfield, Massachusetts, and the Berkshire Mountain Lodge. Featuring 146 one-bedroom condominiums with great amenities like fully-appointed kitchens, individual living and dining areas, and two HD televisions, you will feel... more

Crowne Plaza Hotel Pittsfield – Berkshires

Pittsfield, Massachusetts, United States

Kemble Inn

Lenox, Massachusetts, United States
87
Excellent
51 Reviews
$200

Four seasons of relaxation and excitement awaits for you at the beautiful Kemble Inn. This Berkshires destination combines the stunning architecture of a 125-year-old Gilded Age mansion with completely modern amenities and furnishings for a one-of-a-kind vacation experience. You'll fall in love with the charming mountain vista scenery, the spacious... more

Black Swan Inn

Lee, Massachusetts, United States
$150

Located in the foothills of the Berkshire Mountains, the Black Swan Inn is at the heart of the action of Lee, Massachusetts. Whether you're passing through for the Tanglewood Music Festival, the Norman Rockwell Museum, Lee Premium Outlets or Jacob's Pillow Dance Festival you are sure to find many amenities and accommodations to keep coming back!... more

The Weathervane Inn

Great Barrington, Massachusetts, United States
$151

Located on ten beautifully landscaped acres in the cultural "Mecca" of the Berkshires, the distinctive Weathervane Inn is on the National Register of Historic Places. For excursions to the many outdoor performances in the area, gourmet picnic baskets can be arranged.... more

Brookside & Pondside Country Motel

Williamstown, Massachusetts, United States
$69

Brookside & Pondside Country Motel is an enchanting "retro" property on a brook and a pond. This bed and breakfast features a variety of polished and charming rooms, some featuring Jacuzzis, canopy beds, and parlor stoves. A full hot breakfast buffet is available to all guests, as well as a seasonal heated pool. The properties also offer... more

Vacation Village at Berkshires

Hancock, Massachusetts, United States
84
Very Good
767 Reviews

For years, the fortunate have flocked to the Berkshires Vacation Village timeshares to savor the region's incomparable complement of American history, natural beauty, sporting entertainment, and cultural enrichment. Soak in the charm of a bygone era while visiting the grounds and stately homes of legendary American figures. The scenic hills,... more

The Orchard Hotel

Williamstown, Massachusetts, United States

Jiminy Peak Mountain Resort

Hancock, Massachusetts, United States
78
Good
289 Reviews
$109

Whether you're looking for a romantic getaway, a family vacation, or just a week with friends you'll find exactly what you need to make it a special trip at Jiminy Peak. Standing at the base of the mountain is the 105-suite Country Inn, offering you luxurious rooms with plush beds and fully-equipped kitchenettes. The Country Inn is more than just a... more

Showing 16-30 of 66 Resorts and Lodges

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