The Best Bed & Breakfasts in Massachusetts

Enjoy the sunrise over the Atlantic Ocean on Cape Cod, Massachusetts
Enjoy the sunrise over the Atlantic Ocean on Cape Cod, Massachusetts | © Henk Meijer / Alamy Stock Photo
Photo of Christy Taylor
18 January 2021

Massachusetts is the perfect state to find quaint and unique bed and breakfasts oozing that famous New England charm. Whether you are looking for a romantic seaside getaway or an extended city break, this guide will help you navigate a variety of styles and options, to find your perfect home away from home.

Martin House Inn, Nantucket

Bed and Breakfast
Map View
Martin House Inn, Nantucket
Courtesy of Martin House Inn / Expedia.com
Martin House Inn sits on lovely Nantucket, a tiny island off the coast of Cape Cod. This charming property, built in 1803, has a roof walk offering views over the quaint historic downtown and harbor. Make new friends around the crackling fireplace in the living room, or relax and read a book on the peaceful veranda or around the fountain in the garden. The innkeeper prepares a daily continental breakfast with pastries and fruit and home-baked treats in the afternoon.

The Barrington, Great Barrington

Bed and Breakfast
Map View
The Barrington, Great Barrington
Courtesy of The Barrington / Expedia.com
The intimate Barrington offers seven unique suites, with names like the Serenity Suite, the Old World Escape, or the Rustic Retreat Suite, each with its own decor and style. Complimentary extras and amenities include a pastry basket and pot of coffee delivered to the suites each morning, Keurig coffee makers, a snack bar with muffins and fruit, and spa robes and slippers. The inn is located on Main Street in the heart of town, surrounded by art galleries, restaurants and boutiques.

The Old Harbor Inn, Chatham

Bed and Breakfast
Map View
The Old Harbor Inn, Chatham
Courtesy of The Old Harbor Inn / Expedia.com
Guests are greeted at the Old Harbor Inn by the proprietors, Ray and Judy Braz, who have owned the Inn since 1996, and with a welcome snack basket. Built in 1932 and lovingly renovated, each of the twelve Victorian-decorated rooms come with Gilchrist & Soames toiletries, luxury linens, bathrobes and complimentary soft drinks. The complimentary breakfast, in the form of a continental buffet along with a signature hot entree, is served daily in the airy breakfast room.

Oasis Guest House, Boston

Budget Hotel
Map View
Oasis
Courtesy of Oasis Guest House / Expedia.com
This affordable Brownstone B&B has an excellent location in the enticing Back Bay neighborhood, with several attractions within easy walking distance. The rooms are uncomplicated and comfortable and come with free wifi and flat-screen TVs. Most have private bathrooms, but some have shared single-occupancy ones in the hallway. An expanded continental breakfast is included each morning, with pastries, fruit, cereal, bagels and boiled eggs. Meet fellow travelers in the living room or on the decks located off each floor.
EVERYTHING YOU NEED TO KNOW

Christopher’s by the Bay, Provincetown

Bed and Breakfast
Map View
Christopher’s By The Bay, Provincetown
Courtesy of Christopher’s By The Bay / Expedia.com
The proprietors, Jim and Dave, bought the Victorian building in 2006 after vacationing in Provincetown for many years. Dogs are allowed in the single pet-friendly room but children are not, as the inn aims to promote relaxation. Rooms are named after artists, such as Dali or Rembrandt, and are appointed with antique-style brass bed frames and hardwood floors. Make sure to check room types as some have shared bathrooms instead of private ones. An expanded continental breakfast is served each day.

Why Book With Culture Trip?

  • Free cancellation

    In these uncertain times, cancel or change for free on select properties.

  • Price-match guarantee

    Find a better price on your booking and we’ll match it. Simple.

  • Unbiased & trustworthy

    Book from recommendations handpicked by travel experts.

  • Sherburne Inn, Nantucket

    Bed and Breakfast
    Map View
    Sherburne Inn, Nantucket
    Courtesy of Sherburne Inn / Expedia.com
    Originally a silk factory, Sherburne was divided into two separate buildings in 1844, with the east side becoming an inn in 1870. The comely rooms have windows overlooking the neighborhood or the lovely garden. Bathrooms come with Beekman 1802 spa products; upgraded rooms have tubs along with showers. Breakfast is complimentary, prepared in-house, or in partnership with a local bakery. In the evenings, there is also a wine-and-cheese social hour. Staff will happily recommend their favorite spots and provide guests with towels, beach chairs and coolers.

    The Windflower Inn, Great Barrington

    Bed and Breakfast
    Map View
    The Windflower Inn, Great Barrington
    Courtesy of The Windflower Inn / Expedia.com
    The historic 13-room Windflower Inn was built in 1850 and is the perfect place to relax and unwind. Venture out to explore the restaurants and stores in town, or further afield to hike through the state forests. The rooms are unique – some having floral wallpaper, four-poster beds or sitting areas. The complimentary breakfast can be eaten in the dining room, or outside on the porch, and consists of baked goods, specialty bread, yogurts and assorted hot items.
    EVERYTHING YOU NEED TO KNOW

    Seven Sea Street Inn, Nantucket

    Bed and Breakfast
    Map View
    Seven Sea Street Inn, Nantucket
    Courtesy of Seven Sea Street Inn / Expedia.com
    The bright and cheerful Seven Sea Street Inn is spread across two properties – the more private Guest House that sleeps four, and the Main House, which has 11 rooms. Quarters are furnished with Emley side chairs, a Chippendale chest of drawers, and oak desks and chairs; upgrade to a suite for a cozy fireplace or gas stove. Innkeepers Matt and Claudia are world travelers with plenty of stories to share over the continental breakfast buffet of muffins, pastries, granola and yogurt.

    Clarendon Square, Boston

    Boutique Hotel, Independent Hotel, Bed and Breakfast
    Map View
    Clarendon Square, Boston
    Courtesy of Clarendon Square / Expedia.com
    When approaching the brick exterior of this boutique B&B, you could be forgiven for thinking it’s a refined townhouse. Perfect for a romantic weekend away, spend time lazing on the rooftop sun deck or soaking in the hot tub while admiring the views of Boston. Breakfast is expanded continental and may be savored on the lovely garden deck in the summer. Your welcoming hosts, Stephen and Bobby, will send you off to your stylish rooms that come with Frette linens and Fresh bath products.
    These recommendations were updated on January 18, 2021 to keep your travel plans fresh.

    Cookies Policy

    We and our partners use cookies to better understand your needs, improve performance and provide you with personalised content and advertisements. To allow us to provide a better and more tailored experience please click "OK"