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Lodging

Hampton Inn & Suites by Hilton Berkshires Lenox

445 Pittsfield Road, Lenox, Massachusetts 01240

Make Hampton Inn and Suites your choice among Lenox, MA hotels and enjoy an area of immense natural beauty.

Breakfast Included, Family Friendly Lodging, Free WiFi, Great Location, Honeymoon, Hotel, Inn/Lodge, Jacuzzi, Lenox, Non-Smoking Hotel, Pool

Hampton Inn & Suites by Hilton Lenox Berkshires

Wild Acres Park

South Mountain Road, Pittsfield, Massachusetts 01201

Wild Acres began as a 83-acre tract of land once owned by the Shakers, who built its pond. After the 80-year tenure of the Shakers, it was sold to a private owner who added log cabins and concrete dams to the pond.

Hiking, Outdoor Adventure, Outdoor Seating, Pets Allowed, Pittsfield

Race Brook Falls

143 East St., Sheffield, Massachusetts 01257

Mentions

Race Brook Falls offers five distinct and very scenic sets of waterfalls. In addition to the falls, you can also continue hiking on to the nearby summits of Mt. Everett and/or Mt. Race, both of which offer scenic views.

Family Fun, Hiking, Outdoor Adventure, Pets Allowed, To do and See

Yankee Inn

461 Pittsfield Road, Lenox, Massachusetts 01240

Mentions Reservations

The Yankee Inn offers unique, affordable and beautifully situated lodging in Lenox. Located centrally on route 7, the Yankee Inn offers 111 acres of protected wildlife sanctuary in our back yard, which guests are welcome to explore.

Bar/Lounge, Breakfast Included, Family Friendly Lodging, Fireplace, Fitness Center, Free WiFi, Great Location, Honeymoon, Hotel, Inn/Lodge, Jacuzzi, Lenox, Meeting Room, Non-Smoking Hotel, Pool, Romantic Lodging, Wheelchair Access

Tourists

915 State Road, North Adams, Massachusetts 01247

TOURISTS is a hotel and riverside retreat inspired by the classic American roadside motor lodge, set on the banks of the Hoosic River in the Berkshires city of North Adams. Designed for the 21st century traveler, the 48-room property is a union of de

Hotel, Inn/Lodge, Lodging with a restaurant on property, North Adams & Williamstown

The Red Lion Inn

30 Main St, Stockbridge, Massachusetts 01262

Mentions

Antique-filled rooms, suites, & guesthouses. Contemporary regional cuisine, 3 restaurants, James Beard House-honored chef, elegant & casual/indoor & outdoor dining, award-winning wine list.

Bar/Lounge, Corporate, Family Friendly Lodging, Fireplace, Free WiFi, Honeymoon, Hotel, Lodging with a restaurant on property, Meeting Room, Pets Allowed, Pool, Restaurants, Romantic Lodging, Room Service, Stockbridge, Weddings

Windflower Inn

684 S Egremont Rd, Great Barrington, Massachusetts 01230

Inviting family owned 19th century 13 room Inn & cottage on beautiful 10 acres. Private baths/full breakfast. Near attractions/skiing/hiking/biking/golf. Good for gatherings/reunions.

Bed & Breakfast, Breakfast Included, Family Friendly Lodging, Fireplace, Free WiFi, Great Barrington, Romantic Lodging

Black Swan Inn on the Lake

435 Laurel Street, Lee, Massachusetts 01238

Nestled along the shores of beautiful Laurel Lake in the Berkshires, relaxation and fun await you at the Black Swan Inn.

Fireplace, Fitness Center, Free WiFi, Great Location, Honeymoon, Hotel, Lee, Lodging with a restaurant on property, Meeting Room, Romantic Lodging

Holiday Inn Club Vacations Oak n’ Spruce Resort

190 Meadow St., South Lee, Massachusetts 01239

Reservations

Make more of your stay in the Berkshires at Holiday Inn Club Vacations® Oak n’ Spruce Resort offering vacation fun through all four seasons. Enjoy spacious 1- to 3-bedroom villas complete with a living room and fully equipped kitchen.

Bar/Lounge, Family Friendly Lodging, Fitness Center, Free WiFi, Honeymoon, Hotel, Jacuzzi, Lee, Lodging with a restaurant on property, Luxury & Resorts, Non-Smoking Hotel, Pool, Romantic Lodging

Birchwood Inn

7 Hubbard St, Lenox, Massachusetts 01240

Escape your everyday worries at this Romantic Berkshires bed and breakfast. Relax by a fire in the Library or on our porch in one of our rocking chairs and then stroll down the hill to the Historic Lenox Town Center.

Bed & Breakfast, Breakfast Included, Fireplace, Free WiFi, Honeymoon, Lenox, Pets Allowed, Romantic Lodging

The Porches Inn at MASS MoCA

231 River St, North Adams, Massachusetts 01247

The Porches Inn consists of seven renovated Victorian-era buildings that originally provided housing for the area’s mill workers.

Bar/Lounge, Breakfast Included, Corporate, Family Friendly Lodging, Fitness Center, Free WiFi, Great Location, Honeymoon, Hotel, Jacuzzi, Meeting Room, North Adams & Williamstown, Pool, Restaurants, Romantic Lodging, Weddings

Hotel on North

297 North St, Pittsfield, Massachusetts 01201

Mentions

Honoring the buildings’ long heritage as the legendary menswear and sporting goods emporium Besse-Clarke, they’ve preserved and restored many architectural features that nod to another era…exposed brick walls, tin ceilings, and decorative columns

Bar/Lounge, Breakfast Available, Corporate, Fitness Center, Free WiFi, Great Location, Honeymoon, Hotel, Live Music, Lodging with a restaurant on property, Meeting Room, Non-Smoking Hotel, Pets Allowed, Pittsfield, Restaurants, Romantic Lodging, Room Service, Weddings

Briarcliff Motel

506 Stockbridge Rd, Great Barrington, Massachusetts 01230

Briarcliff is an authentic 1960’s motel which has been transformed into a contemporary, stylish motor lodge for the 21st century traveler.

Breakfast Included, Family Friendly Lodging, Free WiFi, Great Barrington, Inn/Lodge, Pets Allowed

Lanesboro Country Inn

499 S Main St, Lanesborough, Massachusetts 01237

Closed Permanently

The Lanesborough 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.

Free WiFi, Lanesborough, Specialty Lodging

Berkshires Shirakaba Guest House

20 Mallery Rd, New Ashford, Massachusetts 01237

Berkshires Shirakaba is a Japanese-American Bed and Breakfast that is set high on a wooded ridge top in the far north western Massachusetts village of New Ashford.

Bed & Breakfast, Lodging with a restaurant on property, New Ashford, Romantic Lodging, Specialty Lodging

Holiday Inn Express Great Barrington

415 Stockbridge Road, Great Barrington, Massachusetts 01230

The Holiday Inn Express Hotel & Suites Great Barrington is in close proximity to many boutique shops, several ski areas, a host of cultural activities, including Tanglewood, Shakespeare and Company, Barrington Stage Company, and more.

Breakfast Included, Fitness Center, Hotel, Meeting Room, Pool

Super 8 by Wyndham

I-170 Housatonic St Lee, Lee, Massachusetts 01238

Super 8 hotel is an ideal stopping point for your travels through the Berkshires. We put you close to outlet shopping, art galleries, and outdoor recreation.

Breakfast Included, Hotel, Lee, Non-Smoking Hotel, Room Service

33 Main

33 Main St, Lenox, Massachusetts 01240

Conceived and curated by home furnishings entrepreneur and Lenox resident, Annie Selke, 33 Main offers a delightful escape for the discerning traveler.

Bed & Breakfast, Breakfast Included, Fitness Center, Free WiFi, Great Location, Lenox, Pets Allowed, Room Service

Kemble Inn

2 Kemble Street, Lenox, Massachusetts 01240

Elegant, classic architecture creates a stunning backdrop for the large windows, beautiful views, and bold, modern decor at the Kemble Inn.

Bed & Breakfast, Breakfast Included, Corporate, Fireplace, Free WiFi, Great Location, Honeymoon, Hotel, Lenox, Lodging with a restaurant on property, Non-Smoking Hotel, Romantic Lodging, Venues, Weddings

Applegate Inn

279 W Park St, Lee, Massachusetts 01238

Applegate has a unique location - a country estate near Tanglewood, Jacobs Pillow, theatre companies, Norman Rockwell Museum, other cultural and natural wonders, with only a half mile walk to downtown Lee.

Bed & Breakfast, Breakfast Included, Fireplace, Free WiFi, Honeymoon, Jacuzzi, Lee, Meeting Room, Pool

Yankee Suites Extended Stay

20 West Housatonic St., Pittsfield, Massachusetts 01201

Reservations

Enjoy the comfort of home while away from home. Each spacious, efficiency (condo-style) extended stay apartment includes living room, kitchen, bedroom, full bathroom, and deck.

Free WiFi, Hotel, Inn/Lodge, Motel, Pets Allowed, Pittsfield

Yankee Suites Extended Stays Pittsfield Ma

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox, Massachusetts 01201

Mentions Reservations

The Courtyard by Marriott Lenox Berkshires is surrounded by stunning views of the Berkshire hills & located 1 mile from downtown shopping & restaurant district of Lenox.

Bar/Lounge, Breakfast Available, Family Friendly Lodging, Fitness Center, Free WiFi, Great Location, Honeymoon, Hotel, Lenox, Lodging with a restaurant on property, Meeting Room, Non-Smoking Hotel, Pool, Wheelchair Access

Courtyard Marriott in the Berkshires-1.jpg

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, Massachusetts 01201

Mentions Reservations

The Best Western Berkshire Hills Inn & Suites proudly offers 59 spaciously appointed guest rooms each complete with microwave, refrigerator, 37-inch LCD television with HBO® and high-speed Internet access.

Breakfast Included, Family Friendly Lodging, Fitness Center, Free WiFi, Great Location, Hotel, Jacuzzi, Meeting Room, Pittsfield

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The Rose & Goat Retreat

9 Moores Road, City of North Adams, Massachusetts 01247

Come be on top of the world in the wild and beautiful Berkshires, with 50 acres of peaceful serenity on top of the mountain.

Corporate, Honeymoon, North Adams & Williamstown, Romantic Lodging, Specialty Lodging, Venues, Weddings

Gateways Inn & Restaurant

51 Walker Street, Lenox, Massachusetts 01240

Experience the incomparable elegance of The Gateways Inn & Restaurant that will take you to another time and place.

Bar/Lounge, Bed & Breakfast, Breakfast Included, Corporate, Fireplace, Lenox, Live Music, Lodging with a restaurant on property, Meeting Room, Restaurants, Romantic, Romantic Lodging, Upscale, Venues, Weddings

The Red Door

55 Cliffwood St, Lee, Massachusetts 01238

At the Red Door B&B they pride themselves in offering comfort, local organic food, and a central location in the Berkshires.

Bed & Breakfast, Free WiFi, Great Location, Lee, Romantic Lodging

Maplewood Bed & Breakfast

435 Maple St, Hinsdale, Massachusetts 01235

This charming B&B offers two private guest rooms and a two bedroom suite. All rooms are separately air conditioned and have private baths and free Wi-Fi.

Bed & Breakfast, Breakfast Included, Free WiFi, Hinsdale, Romantic Lodging

Stonover Farm Bed and Breakfast

169 Under Mountain Rd, Lenox, Massachusetts 01240

Located on 10 country acres only two miles from Lenox village. Stonover Farm Bed and Breakfast offers a full cooked-to-order breakfast, afternoon wine & cheese, wi-fi, guest computer, free private phones, 14" mattresses, premium linens, robes & more.

Bed & Breakfast, Breakfast Included, Fireplace, Free WiFi, Honeymoon, Lenox, Romantic Lodging

Seven Hills Inn

40 Plunkett Street, Lenox, Massachusetts 01240

Set on 27 acres of rich lawns and sensational gardens, The Seven Hills Inn is the ideal location for your special event.

Bed & Breakfast, Breakfast Included, Corporate, Fireplace, Honeymoon, Lenox, Non-Smoking Hotel, Pets Allowed, Pool, Romantic Lodging, Venues, Weddings

Crabtree Cottage

65 Franklin St, Lee, Massachusetts 01238

In a country house built in 1862, this charming bed-and-breakfast includes a garden, a quaint dining room and a cozy living room with a fireplace and gourmet cooked breakfast is complimentary.

Bed & Breakfast, Breakfast Included, Fireplace, Free WiFi, Lee, Pets Allowed, Romantic Lodging

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