Hotel & Resort
Hampton Terrace Inn
📍91 Walker St, Lenox, Massachusetts, 01240
Posh B&B in a Victorian mansion offering elegant rooms, an outdoor pool & complimentary liqueurs.
Venue
Olio | Historic Wedding & Event Venue
📍43 Main St, Peabody, Massachusetts, 01960
Hotel & Resort
Woods Hole Inn
📍28 Water St, Woods Hole, Massachusetts, 02543
Restored historic inn offering refined rooms with Cape Cod-style, plus a lively restaurant.
Historic Estate
Eustis Estate Museum and Study Center, Historic New England
📍1424 Canton Ave, Milton, Massachusetts, 02186
Hotel & Resort
Stockbridge Country Inn
📍26 Glendale Rd, Stockbridge, Massachusetts, 01262
B&B in a garden setting featuring antique-filled rooms, a fireside lounge & an outdoor pool.
Historic Estate
Proctor Mansion Inn
📍36 Common St, Wrentham, Massachusetts, 02093
Charming rooms in a refined guesthouse with period antiques, plus an ornate dining area.
Vineyard & Winery
Boston Winery
📍26 Ericsson St, Boston, Massachusetts, 02122
Italian-inspired winery offering make-your-own wines plus tastings & tours in an historic building.
Hotel & Resort
Essex Street Inn
📍7 Essex St, Newburyport, Massachusetts, 01950
Victorian B&B featuring genteel rooms & suites, plus continental breakfast, a gym & free Wi-FI.
Hotel & Resort
Sally Webster Inn
📍34 Pleasant St, Rockport, Massachusetts, 01966
Unpretentious rooms decorated with antiques in a warm B&B set in a 19th century home.
Hotel & Resort
Longfellow's Wayside Inn
📍72 Wayside Inn Rd, Sudbury, Massachusetts, 01776
Cozy, antiques-filled rooms in a historic 1707 inn offering a homey restaurant, a bar & a patio.
Hotel & Resort
Chatham Bars Inn
📍297 Shore Rd, Chatham, Massachusetts, 02633
Set by a private beach, this stylish, historic resort offers a kid's program, spa & farm-fresh food.
Hotel & Resort
The Red Lion Inn
📍71 S Main St, Cohasset, Massachusetts, 02025
Historic 18th-century inn with casually chic rooms, an upscale brasserie & a dance bar.
Historic Estate
Bull Mansion Event Space
📍55 Pearl St, Worcester, Massachusetts, 01608
A historic mansion housing a farm-to-table New American restaurant & craft cocktail scene.
Hotel & Resort
Salem Waterfront Hotel & Suites
📍225 Derby St, Salem, Massachusetts, 01970
Classically furnished rooms & suites, plus an indoor heated pool & golf cart rides to the wharf.
Resort
Riviera Beach Resort
📍327 S Shore Dr, South Yarmouth, Massachusetts, 02664
Low-key, seasonal beachfront resort offering classic rooms, plus a kids' club, 2 pools & a cafe.
Historic Estate
Castle Manor Inn
📍141 Essex Ave, Gloucester, Massachusetts, 01930
Victorian inn with a restaurant offering elegant main house rooms & basic motor court units.
Barn / Ranch
Inn On The Horse Farm
📍277 Old Sudbury Rd, Sudbury, Massachusetts, 01776
Quaint B&B in a former 1880 farmhouse offering rooms decorated with antiques & equine art.