Free $50 gift card with a $250+ gift card purchase

Charlestown Bed and Breakfasts

Sort by:

Harbor Light Inn

Marblehead, MA

In the heart of Old Town Marblehead, 200 yards from the harbor, shops & galleries.HDTV's. fireplaces

from $169

4.5 (35)
Accepts:

Visit Website

Harbor Light Inn

Harbor Light Inn

from $169

Marblehead, MA

4.5 (35)

Visit Website

Lotus Place

Cambridge, MA

Lotus Place B&B. Luxurious, newly renovated bed and breakfast. Steps away from Harvard and MIT.

from $99

4.2 (12)

Visit Website

Lotus Place

Lotus Place

from $99

Cambridge, MA

4.2 (12)

Visit Website

The Union Park Guest House

Boston, MA

Ultimate Luxury in the Heart of the City! No Booking Fee! Limited Parking available

from $190

4.3 (21)

Check Dates

Beacon Inn

Brookline, MA

Special rates for longer stays! Extended stay units which include kitchen facilities are available

from $99

3.3 (9)
Accepts:

Visit Website

Beacon Inn

Beacon Inn

from $99

Brookline, MA

3.3 (9)

Visit Website

Moroccan Luxury Suites

Boston, MA

Three-room luxury art suites with Moroccan or European furnishings--elegant, comfortable, romantic!

from $165

4.6 (14)
Accepts:

Check Dates

Moroccan Luxury Suites

Moroccan Luxury Suites

from $165

Boston, MA

4.6 (14)

Visit Website »

Check Dates

Whitman House

Cambridge, MA

Clean Modern Home Tucked in Cambridge, A Great Vacation Any Time Of Year

from $130

4.5 (69)

Check Dates

Whitman House

Whitman House

from $130

Cambridge, MA

4.5 (69)

Visit Website »

Check Dates

Green Turtle Floating Bed and Breakfast

Boston, MA

Come Float With Us! Bed and Breakfast on Boston Harbor

from $225

4.8 (302)

Visit Website

Aisling Bed & Breakfast

Boston, MA

Aisling Bed and Breakfast is located in the Historic Boston neighbourhood of the South End, Bosto...

from $275

4.9 (12)
Accepts:

Visit Website

Aisling Bed & Breakfast

Aisling Bed & Breakfast

from $275

Boston, MA

4.9 (12)

Visit Website

The Inn at Hastings Park

Lexington, MA

Experience Revolutionary Hospitality!

from $250

Visit Website

The Inn at Hastings Park

The Inn at Hastings Park

from $250

Lexington, MA

Visit Website

The College Club of Boston

Boston, MA

Eleven guest rooms offer Back Bay charm, convenience and comfort. Each room's decor is uniquely d...

from $99

4.1 (133)

Check Dates

Free $50 gift card with a $250+ gift card purchase

Emerson Inn By The Sea

Rockport, MA

Sweeping Ocean Views. Historic Hotels of America

from $95

4.5 (52)
Accepts:

Visit Website

Emerson Inn By The Sea

Emerson Inn By The Sea

from $95

Rockport, MA

4.5 (52)

Visit Website

Parkside on Ellery

Cambridge, MA

Parkside on Ellery in Cambridge, Massachusetts has been described by a guest as having “…all the ...

from $150

4.3 (112)

Visit Website

Parkside on Ellery

Parkside on Ellery

from $150

Cambridge, MA

4.3 (112)

Visit Website

Yun's Place, a Boston and Cambridge B&B

Boston, MA

Close to HBS (5 min), Harvard Yard (20 min), metro (20 min). Free Internet, parking.

from $109

4.5 (57)

Visit Website

The Samuel Sewall Inn

Brookline, MA

Built in 1886, as a private residence, The Samuel Sewall Inn boasts beautiful Victorian accommoda...

from $199

4.5 (25)
Accepts:

Visit Website

The Samuel Sewall Inn

The Samuel Sewall Inn

from $199

Brookline, MA

4.5 (25)

Visit Website

Cliffside Bed & Breakfast

Scituate, MA

Welcome to Cliffside Bed and Breakfast. In addition to our lovely rooms, the Cliffside offers gra...

from $135

5.0 (8)
Accepts:

Visit Website

Cliffside Bed & Breakfast

Cliffside Bed & Breakfast

from $135

Scituate, MA

5.0 (8)

Visit Website

Harbor Gardens Inn

Marblehead, MA

The Perfect Getaway in Marblehead MA, gardens, shops, eating all within walking distance

from $135

4.7 (18)
Accepts:

Check Dates

Harbor Gardens Inn

Harbor Gardens Inn

from $135

Marblehead, MA

4.7 (18)

Visit Website »

Check Dates

The Bertram Inn

Brookline, MA

The Bertram Inn offers the opportunity to step back into another era. Built in 1907, The Bertram...

from $199

4.7 (53)
Accepts:

Visit Website

The Bertram Inn

The Bertram Inn

from $199

Brookline, MA

4.7 (53)

Visit Website

The Coolidge Corner Guest House

Brookline, MA

Our beautiful Victorian home, located just 10 minutes from downtown Boston, is a fresh and afford...

from $79

4.3 (124)
Accepts:

Check Dates

The Antrim House & Feathered Nest

Cambridge, MA

Antrim st. is a short walk to MIT or HARVARD, in Inman Sq. close to everything

from $150

4.7 (7)

Visit Website

The Antrim House & Feathered Nest

The Antrim House & Feathered Nest

from $150

Cambridge, MA

4.7 (7)

Visit Website

Bowers House

Somerville, MA

Newly renovated modern B&B, near Tufts, Harvard and MIT, and a short commute to Boston

from $110

4.7 (19)
Accepts:

Visit Website

Bowers House

Bowers House

from $110

Somerville, MA

4.7 (19)

Visit Website

John Jeffries House

Boston, MA

The John Jeffries House is a charming forty-six room inn offering a variety of accomodations, fro...

from $115

3.9 (6)

Visit Website

John Jeffries House

John Jeffries House

from $115

Boston, MA

3.9 (6)

Visit Website

SCHOONER LIBERTY CLIPPER

Boston, MA

Bed and breakfast aboard an historic tall ship in Boston Harbor. Stay and sail with us!

from $55

3.6 (5)

Visit Website

SCHOONER LIBERTY CLIPPER

SCHOONER LIBERTY CLIPPER

from $55

Boston, MA

3.6 (5)

Visit Website

The Quarterdeck Inn by the Sea

Rockport, MA

The Quarterdeck Inn By The Sea is a 8 guest room colonial building that is situated on the rocky ...

from $124

4.3 (17)

Visit Website

The Quarterdeck Inn by the Sea

The Quarterdeck Inn by the Sea

from $124

Rockport, MA

4.3 (17)

Visit Website

The Gilded Lily

Boston, MA

The Gilded Lily is situated at 4 Claremont Park, a quiet residential side street in Boston's Hist...

from $160

4.8 (5)

Visit Website

The Gilded Lily

The Gilded Lily

from $160

Boston, MA

4.8 (5)

Visit Website

La Cappella Suites

Boston, MA

Centrally located in the North End-- Boston's oldest neighborhood and the center of Italian cultu...

from $125

4.2 (17)

Visit Website

La Cappella Suites

La Cappella Suites

from $125

Boston, MA

4.2 (17)

Visit Website

Carolyn's Bed & Breakfast

Cambridge, MA

The perfect destination for college visits, business trips or visiting the Cambridge/Boston area....

from $120

4.4 (16)
Accepts:

Carolyn's Bed & Breakfast

Carolyn's Bed & Breakfast

from $120

Cambridge, MA

4.4 (16)

The Lyttleton Inn

Littleton, MA

The Lyttleton Inn is a restored 19th century farmhouse that sits nestled in the Nashoba Valley, s...

from $105

4.7 (102)

Visit Website

The Lyttleton Inn

The Lyttleton Inn

from $105

Littleton, MA

4.7 (102)

Visit Website

A Lady Winette Cottage B&B

Marblehead, MA

Private beach · Harbor view porch · Secret Garden · Private deck with harbor view

from $125

4.0 (23)

Visit Website

A Lady Winette Cottage B&B

A Lady Winette Cottage B&B

from $125

Marblehead, MA

4.0 (23)

Visit Website

Fox Pond B&B

Marblehead, MA

Welcome to Fox Pond where you will be surrounded by beautiful gardens and and understated elegance.

from $100

4.7 (9)
Accepts:

Visit Website

Fox Pond B&B

Fox Pond B&B

from $100

Marblehead, MA

4.7 (9)

Visit Website

The Mary Prentiss Inn

Cambridge, MA

Experience our historic town by staying in a house whose family was part of early 17th century Ca...

from $129

4.2 (27)
Accepts:

Check Dates

The Mary Prentiss Inn

The Mary Prentiss Inn

from $129

Cambridge, MA

4.2 (27)

Visit Website »

Check Dates

Bed and Breakfast Afloat c/o Constitution Marina

Boston, MA

OPEN MAY 1 - OCTOBER 24 Imagine being lulled to sleep by the gentle motion...

from $175

4.1 (25)

Visit Website

A Cambridge House Inn at Porter

Cambridge,

Close to Tufts, Harvard, Lesley, MIT; short walk to subway into Boston.

from $149

3.7 (17)

Check Dates

Prospect Place

Cambridge, MA

Prospect Place is a wonderful Italianate residence which dates from the mid-Nineteenth cenutry. C...

from $140

4.4 (98)

Visit Website

Prospect Place

Prospect Place

from $140

Cambridge, MA

4.4 (98)

Visit Website

North Bridge Inn

Concord, MA

Located in the heart of historic Concord, Massachusetts, the North Bridge Inn is ideally situated...

from $135

4.3 (113)
Accepts:

Visit Website

North Bridge Inn

North Bridge Inn

from $135

Concord, MA

4.3 (113)

Visit Website

B&B By the Sea

Hull, MA

BB by the Sea is an easy breezy getaway. Minutes to BOSTON and LOGAN airport by ferry.

from $195

4.8 (17)

B&B By the Sea

B&B By the Sea

from $195

Hull, MA

4.8 (17)

Hawthorne Inn

Concord, MA

Relaxed Elegance- An Intimate refuge where History, Literature and Nature entwine.

from $139

4.7 (10)
Accepts:

Visit Website

Hawthorne Inn

Hawthorne Inn

from $139

Concord, MA

4.7 (10)

Visit Website

Yankee Clipper Inn

Rockport, MA

The Yankee Clipper was voted Best Nearby Escape by Boston Magazine & Best Ocean Views by Arri...

from $129

4.2 (15)
Accepts:

Check Dates

Yankee Clipper Inn

Yankee Clipper Inn

from $129

Rockport, MA

4.2 (15)

Visit Website »

Check Dates

The Inn at Castle Hill

Ipswich, MA

Secluded beyond the ornamental iron gates of the Crane Estate and nestled at the foot of Castle H...

from $175

4.2 (4)

Visit Website

The Inn at Castle Hill

The Inn at Castle Hill

from $175

Ipswich, MA

4.2 (4)

Visit Website

Abigayle's Bed and Breakfast

Boston, MA

Our charming brownstone, built in 1896, is set on a quiet, tree lined street adjacent to Kenmore ...

from $105

4.3 (36)

Visit Website

Abigayle's Bed and Breakfast

Abigayle's Bed and Breakfast

from $105

Boston, MA

4.3 (36)

Visit Website

Brimblecomb Hill B&B

Marblehead, MA

Built in 1721 (eleven years before George Washington was born!), Brimblecomb Hill B&B is a warm a...

from $95

4.4 (14)
Accepts:

Visit Website

Brimblecomb Hill B&B

Brimblecomb Hill B&B

from $95

Marblehead, MA

4.4 (14)

Visit Website

Morrison House Bed & Breakfast

Somerville, MA

Homey and tranquil, with every comfort and convenience. Steps from subway in hip Davis Square.

from $75

4.6 (22)
Accepts:

Visit Website

Morrison House Bed & Breakfast

Morrison House Bed & Breakfast

from $75

Somerville, MA

4.6 (22)

Visit Website

Park Lane Bed & Breakfast

Newton, MA

The Park Lane, which provides a sweet alternative to the hub-bub of Boston, is conveniently nestl...

from $100

4.8 (9)

Visit Website

Park Lane Bed & Breakfast

Park Lane Bed & Breakfast

from $100

Newton, MA

4.8 (9)

Visit Website

Josephine's Bed & Breakfast

Hull, MA

Josephine's is a unique B&B experience. The proprietor Ann Marie drew her inspiration from her e...

from $110

4.8 (9)

Check Dates

Captain's House

Rockport, MA

An oceanfront guesthouse with uninterrupted views of Straitsmouth and Thacher Islands.

from $135

4.5 (44)
Accepts:

Visit Website

Captain's House

Captain's House

from $135

Rockport, MA

4.5 (44)

Visit Website

Linden Tree Inn

Rockport, MA

from $105

4.2 (9)
Accepts:

Visit Website

Linden Tree Inn

Linden Tree Inn

from $105

Rockport, MA

4.2 (9)

Visit Website

Alderwood

Newton, MA

from $95

4.8 (8)

Visit Website

Alderwood

Alderwood

from $95

Newton, MA

4.8 (8)

Visit Website

Morgan's Rest

Lexington, MA

from $125

4.3 (57)
Accepts:

Visit Website

Morgan's Rest

Morgan's Rest

from $125

Lexington, MA

4.3 (57)

Visit Website

The Tuck Inn B&B

Rockport, MA

from $125

4.7 (7)

Visit Website

The Tuck Inn B&B

The Tuck Inn B&B

from $125

Rockport, MA

4.7 (7)

Visit Website

from $120

4.2 (5)

Visit Website

Cambridge Bed Breakfast on Maple

Cambridge Bed Breakfast on Maple

from $120

Cambridge, MA

4.2 (5)

Visit Website

from $95

3.5 (2)
Accepts:

Visit Website

A Bed & Breakfast In Cambridge

A Bed & Breakfast In Cambridge

from $95

Cambridge, MA

3.5 (2)

Visit Website

from $129

4.0 (8)
Accepts:

Check Dates

The Inn @ St. Botolph

The Inn @ St. Botolph

from $129

Boston, MA

4.0 (8)

Visit Website »

Check Dates

from $150

4.4 (7)

Visit Website

The 1684 John Burnham House

The 1684 John Burnham House

from $150

Essex, MA

4.4 (7)

Visit Website

Blue's Bed & Breakfast

Cambridge, MA

from $110

3.7 (3)
Accepts:

Visit Website

Blue's Bed & Breakfast

Blue's Bed & Breakfast

from $110

Cambridge, MA

3.7 (3)

Visit Website

Oceanside Inn

Scituate,

from $109

4.1 (3)

Visit Website

Oceanside Inn

Oceanside Inn

from $109

Scituate,

4.1 (3)

Visit Website

from $125

4.5 (17)

Visit Website

Village Bed and Breakfast

Village Bed and Breakfast

from $125

Marshfield,

4.5 (17)

Visit Website

from $135

4.4 (24)
Accepts:

Visit Website

Wellesley Bed and Breakfast

Wellesley Bed and Breakfast

from $135

Wellesley, MA

4.4 (24)

Visit Website

Arbor House

Marblehead, MA

from $125

4.8 (19)
Accepts:

Visit Website

Arbor House

Arbor House

from $125

Marblehead, MA

4.8 (19)

Visit Website

from $140

4.7 (4)

Visit Website

Encore Bed & Breakfast

Encore Bed & Breakfast

from $140

Boston, MA

4.7 (4)

Visit Website

Seafarer Inn

Rockport, MA

from $159

4.0 (3)
Accepts:

Visit Website

Seafarer Inn

Seafarer Inn

from $159

Rockport, MA

4.0 (3)

Visit Website

The Christopher

Boston, MA

from $100

3.5 (27)
Accepts:

Check Dates

The Christopher

The Christopher

from $100

Boston, MA

3.5 (27)

Visit Website »

Check Dates

Rockwell Haven

Cambridge, MA

from $160

4.9 (4)

Visit Website

Rockwell Haven

Rockwell Haven

from $160

Cambridge, MA

4.9 (4)

Visit Website

from $130

4.9 (49)

Visit Website

Amerscot House Inn

Amerscot House Inn

from $130

Stow, MA

4.9 (49)

Visit Website

Irving House At Harvard

Cambridge, MA

from $75

4.3 (21)

Check Dates

Irving House At Harvard

Irving House At Harvard

from $75

Cambridge, MA

4.3 (21)

Visit Website »

Check Dates

The Salem Inn

Salem, MA

from $129

3.4 (9)
Accepts:

Visit Website

The Salem Inn

The Salem Inn

from $129

Salem, MA

3.4 (9)

Visit Website

Seven South Street Inn

Rockport, MA

from $99

4.8 (64)
Accepts:

Visit Website

Seven South Street Inn

Seven South Street Inn

from $99

Rockport, MA

4.8 (64)

Visit Website

Proctor Mansion Inn

Wrentham, MA

from $105

5 (3)
Accepts:

Check Dates

Proctor Mansion Inn

Proctor Mansion Inn

from $105

Wrentham, MA

5 (3)

Visit Website »

Check Dates

The Gryphon House

Boston, MA

from $189

4.5 (9)
Accepts:

Visit Website

The Gryphon House

The Gryphon House

from $189

Boston, MA

4.5 (9)

Visit Website

Harding House

Cambridge, MA

from $95

4.5 (70)
Accepts:

Check Dates

Harding House

Harding House

from $95

Cambridge, MA

4.5 (70)

Visit Website »

Check Dates

A Room at the Top

Cambridge, MA

from $95

4.1 (9)

A Room at the Top

A Room at the Top

from $95

Cambridge, MA

4.1 (9)

from $140

4.7 (25)

Visit Website

The Seagull Inn Bed and Breakfast

The Seagull Inn Bed and Breakfast

from $140

Marblehead, MA

4.7 (25)

Visit Website

Nolan House

Boston, MA

from $150

3.8 (9)

Visit Website

Nolan House

Nolan House

from $150

Boston, MA

3.8 (9)

Visit Website

Sally Webster Inn

Rockport, MA

from $140

4.5 (95)
Accepts:

Check Dates

Sally Webster Inn

Sally Webster Inn

from $140

Rockport, MA

4.5 (95)

Visit Website »

Check Dates

from $135

4.8 (3)
Accepts:

Visit Website

The Inn at Scituate Harbor

The Inn at Scituate Harbor

from $135

Scituate, MA

4.8 (3)

Visit Website

from $75

4.5 (20)
Accepts:

Visit Website

This Old House Bed and Breakfast

This Old House Bed and Breakfast

from $75

Lexington, MA

4.5 (20)

Visit Website

from $99

4.2 (32)
Accepts:

Check Dates

Harborside House

Marblehead, MA

from $90

4.8 (57)

Visit Website

Harborside House

Harborside House

from $90

Marblehead, MA

4.8 (57)

Visit Website

Pink House on Gerry B&B

Marblehead, MA

from $80

4.8 (15)

Visit Website

Pink House on Gerry B&B

Pink House on Gerry B&B

from $80

Marblehead, MA

4.8 (15)

Visit Website

from $100

4.9 (2)

Visit Website

The Colonial Inn Gloucester

The Colonial Inn Gloucester

from $100

Gloucester, MA

4.9 (2)

Visit Website

from $140

4.2 (19)

Visit Website

Gray House Cambridge Accommodations

Gray House Cambridge Accommodations

from $140

Cambridge, MA

4.2 (19)

Visit Website

Pleasant Street Inn

Rockport, MA

from $115

Accepts:

Visit Website

Pleasant Street Inn

Pleasant Street Inn

from $115

Rockport, MA

Visit Website

Country Garden Inn

Rowley, MA

from $109

4.2 (79)
Accepts:

Check Dates

Country Garden Inn

Country Garden Inn

from $109

Rowley, MA

4.2 (79)

Check Dates

from $125

Spring Hill House

Spring Hill House

from $125

Stow, MA

Carruth House

Boston, MA

from $95

4.4 (13)

Carruth House

Carruth House

from $95

Boston, MA

4.4 (13)

Joans Bed & Breakfast

Peabody, MA

from $75

4.7 (42)

Joans Bed & Breakfast

Joans Bed & Breakfast

from $75

Peabody, MA

4.7 (42)

from $115

3.9 (8)

Rutland Square House

Rutland Square House

from $115

Boston, MA

3.9 (8)

No results were found.

Your search was a little too specific.We suggest reducing the filters or searching for a different city.

Sponsored Links

Book a getaway today

Best Price Guarantee

We offer the Best Price Guarantee! Learn more

Recent reviews

Cambridge Bed Breakfast on Maple

$120 - $140

4.2 (5)

"My husband and I stayed here 3 days while visiting my daughter. The location near Inm..."

Read more...


This Old House Bed and Breakfast

$75 - $100

4.6 (20)

"The furnishings are beautiful and the breakfast is fantastic with real silver and chi..."

Read more...


Morgan's Rest

$125 - $145

4.3 (57)

"Excellent B & B to relax after long days with relatives. Just the right amount of..."

Read more...


View More Reviews

Charlestown B&B reviews

Overall rating:

The Charlestown B&B review score is based on feedback from travelers from around the world. See property page for full, detailed reviews by real travelers.

Top