Looking for Romantic hotels, inns, and B&Bs in the Berkshires? We've compiled a list based on Tripadvisor's rankings for most romantic stays in the Berkshires.
ALL A B C D E F G H I J K L M N O P Q R S T U V W X Y Z
461 Pittsfield Road, Lenox, Massachusetts 01240
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
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.
30 Main St, Stockbridge, Massachusetts 01262
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
Antique-filled rooms, suites, & guesthouses. Contemporary regional cuisine, 3 restaurants, James Beard House-honored chef, elegant & casual/indoor & outdoor dining, award-winning wine list.
684 S Egremont Rd, Great Barrington, Massachusetts 01230
Bed & Breakfast, Breakfast Included, Family Friendly Lodging, Fireplace, Free WiFi, Great Barrington, Romantic Lodging
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.
435 Laurel Street, Lee, Massachusetts 01238
Fireplace, Fitness Center, Free WiFi, Great Location, Honeymoon, Hotel, Lee, Lodging with a restaurant on property, Meeting Room, Romantic Lodging
Nestled along the shores of beautiful Laurel Lake in the Berkshires, relaxation and fun await you at the Black Swan Inn.
190 Meadow St., South Lee, Massachusetts 01239
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
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.
7 Hubbard St, Lenox, Massachusetts 01240
Bed & Breakfast, Breakfast Included, Fireplace, Free WiFi, Honeymoon, Lenox, Pets Allowed, Romantic Lodging
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.
231 River St, North Adams, Massachusetts 01247
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
The Porches Inn consists of seven renovated Victorian-era buildings that originally provided housing for the area’s mill workers.
297 North St, Pittsfield, Massachusetts 01201
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
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
20 Mallery Rd, New Ashford, Massachusetts 01237
Bed & Breakfast, Lodging with a restaurant on property, New Ashford, Romantic Lodging, Specialty Lodging
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.
2 Kemble Street, Lenox, Massachusetts 01240
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
Elegant, classic architecture creates a stunning backdrop for the large windows, beautiful views, and bold, modern decor at the Kemble Inn.
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