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Romantic Hotel Search: United States > Massachusetts

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Romantic Places in Massachusetts

Berkshires, Massachusetts
An idyllic corner of New England that mixes high culture with a neo-bohemian atmosphere of artists, artisans and rural farmhouse simplicity.

16 Blantyre Rd.
Lenox, Mass
T: +1 (413) 637-3556. 23 rooms; US$ 675-
1902 Tudor mansion set in 85 acres of lawn and woodland offering friendly service and luxurious aristocratic style.

Lenox, MA
T: +1 413 637 0610. 19 rooms, US$ 715-
An elegant Massachusetts romantic hotel located next to Tanglewood. This Gilded Age “cottage” built in the style of a l6th century Florentine palazzo sits on 22 acres in a Frederick Law Olmsted designed parkland.

Hampton Terrace b&b
91 Walker St.
Lenox, MA
T: +1 (413) 637-1773.  $249 (off-season) – $329 (high season)
Built in 1897, the highly-rated  mansion features a heated swimming pool and many rooms with fireplaces and/or Jacuzzis. The elegant house is perfectly located – just off Main St. – for exploring Lenox’s unique shops and good restaurants.

Birchwood Inn
7 Hubbard St.
Lenox, Mass
T: +1 (413) 637-2600. 16 rooms. US$ 190-
Afternoon tea and delicious breakfasts at this l766 house with fireplaces and gorgeous views.  Located a two minute walk to downtown Lenox.

The Briarcliff Motel
506 Stockbridge Rd.
Great Barrington, MA
T: 413.528.3000. 19 rooms. $170-, high season.
A chic modern counterpoint to the above hotels. Once a typical 1960’s roadside motel, it was tastefully renovated in 2011 by a British couple.

Stonover Farm
169 Under Mountain Road
Lenox, MA
T: +1 413 637-9100. 5 room b&b. US$ 425-, high season
A former record producer runs this elegant 100 year old farmhouse inn. The inn stands beside a spring-fed duck pond on 8 country acres with magnificent trees, lawns and forest, and is less than a mile from the Tanglewood main gate.

North Adams, Massachusetts
Stylish, edgy and chic former working class milltown, home to the wonderful Massachusetts Museum of Contemporary Art (Mass MoCA), set at the foot of the Berkshires.

The Porches Inn
231 River St.
North Adams, Massachusetts
T: +1 413 664-0400. US$ 180-, high season
Former Victorian workers’ row-house, now an “Industrial-granny chic” boutique hotel located across the street from MoCA. Breakfast delivered in a lunch pail; rocking chairs on the porch.

Martha’s Vineyard, Massachusetts
An East Coast beach island favored by artists, actors and politicians.

Charlotte Inn
27 S. Summer St.,
Edgartown Martha’s Vineyard, Mass
T: +1 508 627 4151. 19 rooms. US$ 550-
Ralph Lauren’s English Mahogany look in an 1864 merchants house, in-town sophistication.

Outermost Inn
Lighthouse Rd., Gay Head
Martha’s Vineyard, Mass
T: +1 508 627 3511. 7 rooms. US$ 340-, high season
For rural beauty it doesn’t get any better than this gray shingled house on a bluff overlooking the cliffs. Shaker style furniture, herb and vegetable gardens.

Menemsha Inn & Cottages
North Rd., Menemsha
Martha’s Vineyard, Mass
T: +1 508 645 2521. 21 rooms. US$ 295-, high season
Secluded and simply furnished in “summer camp” style, located within walking distance of Menemsha village. A famed Life magazine photographer spent 53 summers here. Good water views.

Thorncroft Inn
278 Main St., Vineyard Haven
Martha’s Vineyard, Mass
T: +1 508 693 3333. 14 rooms. US$ 295-, high season
A quiet country inn, the main building was originally a guesthouse of the adjacent oceanfront estate. Private hot tubs available.

Hob Knob
Martha’s Vineyard, Mass
T: +1 508 627 9510. 17 room b&b. $500-

The 19th Gothic revival house has been tastefully updated with a mix of antiques and whimsical furnishings.

Nantucket, Massachusetts
Cedar-shake houses, grasslands, sandy beaches and cobblestoned roads adorn this former whaling island. The island throngs in July and August with wealthy summer residents and tourists.

Nantucket, Mass
T: +1 508 228 0145. 31 rooms. US$ 540-
Wide lawn behind this mansion stretches to 26 miles of Nantucket Bay beachline.

Union Street Inn
7 Union Street
Nantucket, MA
T: + 1 508 228-9222. 12 rooms.
Recently renovated boutique inn located a block off downtown and the harbor.

Cape Cod, Massachusetts
Miles of island coastline, quaint villages, historic harbors and scenic byways.

Chatham Inn at 359 Main St.
359 Main St.
Chatham, MA 02633
T: +1 (508) 945-9232
This 5-star newly renovated and decorated boutique hotel is set in a beautiful, quintessential New England village boasting breathtaking beaches.  The inn is  located at the quiet edge of Main St. just a few minutes walk from unique shops and good restaurants or from the beach.

Salt House Inn
Conwell St., Provincetown, MA
Provincetown, Massachusetts
T: +1 508.487.1911
Converted from historic lodgings, this is the first boutique hotel in Provincetown.

Provincetown Hotel at Gabriels
102 Bradford Street
Provincetown, MA
T: +1 508 487-3232. 18 rooms.
Upscale inn with 4 historic buildings, centrally located, one block from beach.

Boston – Beacon Hill
Beacon Hill has narrow cobblestoned streets, gas lamps and red brick 19th century houses. A well-preserved National Historic District, Beacon Hill has been a favored address of Boston’s elites from John Adams to JFK.

XV Beacon
15 Beacon
Beacon Hill, Boston, MA
T: +1 617 670-1500. 63 rooms. US$ 425-
Stylish rooms in a 1903 Beaux Arts building.

Boston – Cambridge
Across the Charles Bridge from Boston are the historic squares of Cambridge, home to cafés, bookstores, museums and two great universities, Harvard and M.I.T.

Hotel Veritas
Harvard Square
Boston, MA
T: +1 617 520-5000. 31 rooms. US$ 300-
Luxury boutique hotel with small chic rooms decorated in a glamorous Art Deco style.

Northwest Massachusetts

Deerfield Inn
81 Old Main Street
Deerfield, MA
T:  +1 
413 774-5587. 24 rooms.
Historic landmark inn located in an unspoiled 350 year old tree-lined village off Hwy 91.

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