Want travel alerts for this area?

Enter your name and email to receive alerts when new vacation deals are added to any property in this region.

By clicking "Submit" you are agreeing to the
Terms of Service.

Alert successfully created!

Go to Map View

Filters

Avg. Daily Rate
Resort Type
Activities
Amenities

Showing 31-45 of 66 Resorts and Lodges

Birchwood Inn

Lenox, Massachusetts, United States
89
Excellent
28 Reviews

Thornewood Inn & Restaurant

Great Barrington, Massachusetts, United States
81
Very Good
32 Reviews
$76

The Thornewood Inn, located in the heart of the beautiful Berkshire Hills, is the perfect place to vacation in any season. Conveniently situated at the base of Monument Mountain on five acres, the Inn is adjoined by a state forest and offers walking trails that double as cross country ski trails in winter when mother nature cooperates.... more

Rodeway Inn Lee

Lee, Massachusetts, United States

Chesapeake Inn

Lenox, Massachusetts, United States
$151

Chesapeake Inn of Lenox in the Berkshires is only one quarter mile from Tanglewood's East Gate and one mile from the center of Lenox. Rooms feature queen sized beds, private baths, central air conditioning, fresh cut flowers. Pampering personal service includes full breakfast, newspapers, after concert snacks. Heated 75' lap pool.... 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

Devonfield Inn

Lee, Massachusetts, United States
92
Excellent
39 Reviews
$151

Located in the heart of the Berkshires, luxurious Devonfield is world in itself. For the enjoyment of its guests, Devonfield features a heated swimming pool, tennis court, bicycles, and acres of lawn perfect for cross country skiers. Its convenient location offers access to the Berkshire Theatre Festival, Tanglewood, Jacob's Pillow, and fine... 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

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

Harbour House Inn

Cheshire, Massachusetts, United States

Blantyre

Lenox, Massachusetts, United States
$251

"America's Consummate Estate Sanctuary" -Andrew Harper's Hideaway Report Open May 14th through November 7th, 1999... more

Hampton Terrace Bed and Breakfast Inn

Lenox, Massachusetts, United States
96
Excellent
14 Reviews
$175

Bask in the Gilded Age during your stay at the Hampton Terrace Bed & Breakfast Inn. Step back – to an era of hope and prosperity. This historic inn has been renovated and restored to preserve its Gilded Age glory. Once the playground of the rich and famous (Vanderbilts and Carnegies), the Hampton Terrace Bed & Breakfast Inn is... more

Jericho Valley Inn

Williamstown, Massachusetts, United States
78
Good
32 Reviews
$76

The Jericho Valley Inn is located on 350 pristine acres in the beautiful Berkshire Mountains of western Massachusetts. Enjoy the rich cultural offerings in and around Tanglewood or take advantage of Jericho Valley's special ski and golf packages.... more

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

Berkshire Mountain House

Hancock, Massachusetts, United States

The Cornell In Lenox

Lenox, Massachusetts, United States
92
Excellent
175 Reviews
$120

The Cornell in Lenox offers peaceful Berkshire vacations with the historic charm of New England. This unique bed & breakfast is composed of three historic buildings, dating back as far as 1777! Each guestroom and suite features period-style d├ęcor, with charming touches like print wallpaper, painted cupboards, vintage toys & four poster... more

Showing 31-45 of 66 Resorts and Lodges

statsstats