Tourism Development Office
400 High Street
Chestertown, MD. 21620
410-778-0416 | email:tourism@kentcounty.com







LODGING IN KENT COUNTY
B&B's, Motels, Hotels | Vacation Rentals

Clickable Image Rock Hall Mitchell House Comment Comment Mears Great Oak Mears Great Oak Lodge Chestertown Lodging Claddaugh Farm B & B Kentfields Farm
Click on map for websites.
Click on Chestertown or Rock Hall for detailed maps showing locations of accommodations in those towns.

Accommodation Availability

Below is a list of motels, hotels, bed and breakfasts and inns throughout the County.
If the accommodation has a website, it is linked from the icon.

B&B's, Motels, Hotels


CHESTERTOWN AREA

APRIL INN
Next to Washington College and just a short stroll from the historic district.
410-778-3603

Bittersweet

BITTERSWEET GUEST SUITES
Upstairs over the store in downtown Chestertown
410-778-2300


Brampton

BRAMPTON B & B
Magnificent national register plantation house on 35 acres.Located just south of the town limits.
410-778-1860
Toll Free - 866-305-1860

Claddaugh

CLADDAUGH FARM
Stately farmhouse, inviting stop for Eastern Shore travelers. Within 5 miles of Chestertown.
410-778-4894


Comfort Suites

COMFORT SUITES
Modern conveniences with 53 rooms. Close to Chestertown's Historic District.
410-810-0555

COURTYARD INN
Just three miles from Chestertown.
410-778-2755


Driftwood Inn

DRIFTWOOD INN
Traditional hospitality and luxurious accomodations. Close to
Chestertown's Historic District.
410-778-3200

GREAT OAK MANOR
Elegant Waterfront Manor House with spectacular Chesapeake Bay sunsets
off a private beach. Located approximately 10 miles from Chestertown.
800-504-3098


 

HOLIDAY INN EXPRESS
Modern convience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary. Located on Scheeler Rd, Chestertown, Maryland.
410.778.0778

IMPERIAL HOTEL
Beautifully restored Victorian hotel
in the heart of the Historic District.
410-778-5000
Toll Free - 800-295-0014


Mitchell

INN AT MITCHELL HOUSE
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
410-778-6500

Hill's Inn

JOHN L. STAM HOUSE
Restored Victorian, continental breakfast and afternoon tea.Within blocks of the Historic District of Chestertown.
410-778-1926


 

THE KENTFIELDS FARM
A country estate located within 5 miles of Chestertown on the Jarrett Creek.
410-638-2348

Lauretum

LAURETUM INN
Victorian Manor on the Hill. Relaxing and picturesque.On the outskirts of Chestertown.
800-742-3236


Great Oak Lodge

MEARS GREAT OAK LODGE
28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
410-778-2100

Rolph's Wharf


RIVER INN AT ROLPH'S WHARF
Victorian Farmhouse on the shores of the Chester River. Approximately 3 miles from Chestertown.
800-894-6347


STEPNE MANOR
Historic Home available
for Weekend and Weekly rentals.
410-810-1845

WHITE SWAN TAVERN
Impeccably restored 18th century tavern. "Afternoon tea served daily."
410-778-2300


Widows Walk

WIDOW'S WALK INN
Victorian gem located in Chestertown's Historic District
410-778-6455

 


GALENA/GEORGETOWN


Carrousel

THE CARROUSEL HORSE B & B
Elegant and comfortable Victorian inn within a mile of the
Sassafras River yacht marinas
410-648-5476

ROSEHILL FARM B & B
Quiet country B&B on a 100 acre farm
410-648-5334


ROCK HALL AREA


Bay Breeze

BAY BREEZE INN
Cozy, convenient and relaxed in the Eastern Shore tradition
410-639-2061

Black Duck

BLACK DUCK INN
A Waterfront Bed and Breakfast
(410) 639-2478


Carriage House

THE CARRIAGE HOUSE
A very special B & B near the Bay and the Haven.
410-639-2855

Huntingfield

INN AT HUNTINGFIELD CREEK
On the shores of the Chesapeake in the heart of a working farm. Approximately 1/2 mile from Rock Hall.
410-639-7779


Inn at Osprey

THE INN AT OSPREY
Elegant lodging and fine dining on the water
410-639-2194

Mariners

THE MARINER'S MOTEL
A great motel on the harbor. Old Rock Hall favorite
410-639-2291


Moonlight Bay

MOONLIGHT BAY MARINA & INN
A touch of class by the shores of the bay
410-639-2660

North Point

NORTH POINT MARINA & MOTEL
Best view of Chesapeake Bay with all rooms waterfront
410-639-2907


OLD GRATITUDE HOUSE
Elegant bed and breakfast on the water's edge.
410-639-7448

Swan Point

PRUITT'S SWAN POINT INN
Overlooking Swan Creek with delightful rooms & casual dining.
410-639-2500


Spring Cove Manor

SPRING COVE MANOR
A beautiful, secluded waterfront B&B on 8 wooded acres
410- 639-2061

Swan Haven

SWAN HAVEN 
Quiet waterfront getaway in the heart of waterman's country.
410-639-2527


Tallulah's

TALLULAH'S ON MAIN
Deluxe efficiency appartments right in the center of things
410-639-2596

 

 


VACATION RENTALS

THE KENTFIELDS FARM
A country estate located within 5 miles of Chestertown on the Jarrett Creek.
410-778-4181

THE RIVER HOUSE ON MOON BAY
Four bedroom waterfront home outside Chestertown with outstanding views, billards room and more. Available year round for weekly rentals. 1-866-398-2722.


TALLULAH'S BAYFRONT VACATION HOMES
Waterfront & Bay front vacation homes and extended stay needs
410-639-2596

THE OVERLOOK ON MAIN
One two bedroom apartment with bath and full kitchen located in the center of town.
410-639-2855



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