Showing 1-8 of 8 Inns and B&Bs.

rates from
$60

Driftwood Inn

Chestertown, Maryland, United States

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Rest and relax at this 28-room Inn, conveniently located in peaceful Chestertown. Lounge on your spacious colonial-style bed or splash in the outdoor pool. Some rooms even feature a jacuzzi style tub! And Driftwood Inn is within easy distance of all... more

  • Property Size: 28 units
  • Open Dates: Open Year Round
  • Nearby City: Chestertown
  • Nearby Water: Chester River
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes

Inns and B&B Type(s): Family, Romantic

Data Provided By: Driftwood Inn

Brampton Bed & Breakfast Inn

Chestertown, Maryland, United States

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Finished in 1860 as the plantation house of the areas largest peach grower; Brampton retains today nearly all of its original details. They include the magnificent three and a half story central staircase, walnut windows and doors, original heart pine floors and plaster ceiling medallions. This thirty-five acre estate is conveniently located... more

  • Property Size: N/A
  • Open Dates: Open Year Round
  • Nearby City: Chestertown
  • Nearby Water: N/A
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes
Data Provided By: Brampton Bed & Breakfast Inn
rates from
$109

The Inn at Mitchell House

Chestertown, Maryland, United States

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Put yourself in the midst of American history by staying at Mitchell House. Rest in one of the six comfortable rooms or, for added privacy, relax in the one-bedroom Stone’s Throw Cottage. This colonial house is just minutes away from Historic... more

  • Property Size: 6 units
  • Open Dates: Open Year Round
  • Nearby City: N/A
  • Nearby Water: N/A
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes

Inns and B&B Type(s): Historical, Romantic

Data Provided By: The Inn at Mitchell House

White Swan Tavern

Chestertown, Maryland, United States

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The White Swan Tavern, a quiet, elegant home embedded in the history of Maryland's Eastern Shore, is for those who treasure serene streets, birdsong mornings, impeccable service and the grace of New World Tradition. The White Swan tavern has been restored to its 1793 appearance but its fascinating history predates 1733.... more

  • Property Size: N/A
  • Open Dates: Open Year Round
  • Nearby City: Chestertown
  • Nearby Water: N/A
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes
Data Provided By: White Swan Tavern
rates from
$159

Great Oak Manor

Chestertown, Maryland, United States

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Built in 1938 as a private residence for Russell D’Oenche, the Georgian-style Great Oak Manor is an experience in elegance you won’t soon forget! Unwind in one of 12 gracious period-themed guest rooms featuring private baths, balconies with Chesapeake Bay views, and replica antiques. And, make sure to roam the beautifully manicured lawns, enjoy... more

  • Property Size: 12 units
  • Open Dates: Open Year Round
  • Nearby City: Chestertown
  • Nearby Water: N/A
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: No

Inns and B&B Type(s): Historical, Romantic, Spa

Data Provided By: Great Oak Manor
rates from
$130

Lauretum Inn Bed and Breakfast

Chestertown, Maryland, United States

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Five beautifully furnished rooms, each with its own private bath, await you at Lauretum Inn Bed and Breakfast. Savor a delicious continental breakfast, then take one of the inn's bikes for a spin. And, as a guest to Lauretum Inn, you are entitled to... more

  • Property Size: 5 units
  • Open Dates: Open Year Round
  • Nearby City: Chestertown, Maryland
  • Nearby Water: Chester River
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes

Inns and B&B Type(s): Historical, Romantic, Spa

Data Provided By: Lauretum Inn Bed and Breakfast
rates from
$119

Simply Bed & Bread

Chestertown, Maryland, United States

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With only two rooms in this quiet and comfortable guest house, you’ll feel right at home at Simply Bed and Bread. Sit on one of the inviting wicker chairs on the porch and look over Chestertown, Maryland. Inside, delicious treats like fresh... more

  • Property Size: 2 units
  • Open Dates: Open Year Round
  • Nearby City: Chestertown, Maryland
  • Nearby Water: Chester River
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes

Inns and B&B Type(s): Family, Romantic

Data Provided By: Simply Bed & Bread
rates from
$105

Widow's Walk Inn

Chestertown, Maryland, United States

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Located in historic Chestertown on Maryland’s upper eastern shore, Widow’s Walk Inn provides comfortable lodging in its five rooms with the warm atmosphere of a family home. Whether you play a game or read a book in the parlor or relax... more

  • Property Size: 5 units
  • Open Dates: Open Year Round
  • Nearby City: Chestertown, Maryland
  • Nearby Water: Chester River
  • Conference Facility: No
  • Restaurant Onsite: No
  • Pets Allowed: No
  • Kids Allowed: Yes

Inns and B&B Type(s): Historical, Romantic

Data Provided By: Widow's Walk Inn

Showing 1-8 of 8 Inns and B&Bs.

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