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.

B&B's, Motels, Hotels

 


Chestertown
Chestertown Area
Galena
Rock Hall
Vacation Rentals

Lodging in Chestertown

April Inn
Contact:Phyllis and Maria Lauro
407 E. Campus Ave.
Chestertown, MD 21620
Phone: 410-778-3603
Email: aprilinn@verizon.net
URL: www.chestertown.com/lodging/
Next to Washington College and just a short stroll from the historic district.
Bittersweet Guest Suites
Contact:Mary Meisel
231 High Street
Chestertown, MD 21620
Phone: 410.778.2300
Email: info@whiteswantavern.com
URL: www.whiteswantavern.com
Upstairs over the store in downtown Chestertown
Comfort Suites
Contact:Manager
160 Scheeler Road
Chestertown, MD 21620
Phone: 410.810.0555
Email: n/a
URL: chestertown.com/comfortsuites
Modern conveniences with 53 rooms. Close to Chestertown's Historic District.
Driftwood Inn
Contact:Neil & Vicki Desai
609 Washington Avenue
Chestertown, MD 21620
Phone: 410-778-3200
Email: driftwoodinn@yahoo.com
URL: www.driftwoodinnchestertown.com
Traditional hospitality and luxurious accomodations. Close to Chestertown's Historic District.
Holiday Inn Express
Contact:Manager
150 Scheeler Road
Chestertown, MD 21620
Phone: 410.778.0778
Email: n/a
URL: www.ichotelsgroup.com
Modern convience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary. Located on Scheeler Rd, Chestertown, Maryland.
Imperial Hotel
Contact:Joe Dolce
208 High Street
Chestertown, MD 21620
Phone: 410.778.5000
Email: Staff@imperialchestertown.com
URL: www.imperialchestertown.com
Beautifully restored Victorian hotel in the heart of the Historic District.
John M. Stam House (Hills Inn
Contact:Innkeeper
114 Washington Ave
Chestertown, MD 21620
Phone: 410-778-1926
Email: n/a
URL: www.kentcounty.com/lodging
Restored Victorian, continental breakfast and afternoon tea.Within blocks of the Historic District of Chestertown.
Lauretum Bed & Breakfast Inn
Contact:
954 High Street
Chestertown, MD 21620
Phone: (800) 742-3236
Email: innkeeper@lauretuminn.com
URL: www.lauretuminn.com
A long winding lane invites you to Lauretum (1881), sitting splendidly atop a tree graced knoll on six acres in Chestertown, MD. The complex form and massing of the house reflect the eclecticism of the late Victorian period.
White Swan Tavern
Contact:Mary Meisel
231 High Street
Chestertown, MD 21620
Phone: (410) 778-2300
Email: info@whiteswantavern.com
URL: www.whiteswantavern.com
Impeccably restored 18th century tavern. "Afternoon tea served daily.
Widow's Walk Inn
Contact:Bob & Susan Lathroum, Innkeepe
402 High Street
Chestertown, MD 21620
Phone: 410-778-6455
Email: n/a
URL: www.chestertown.com/widow
Victorian gem located in Chestertown's Historic District

Chestertown
Near Chestertown
Galena
Rock Hall
Vacation Rentals

Lodging in the Chestertown area

Brampton Bed & Breakfast Inn
Contact: Mike & Danielle Hanscom
25227 Chestertown Road
Chestertown, MD 21620
Phone: 410.778.1860
Email: innkeeper@bramptominn.com
URL: www.bramptoninn.com
Magnificent national register plantation house on 35 acres.Located just south of the town limits.
Claddaugh Farm
Contact: Missy Hollis
160 Claddaugh Lane
Chestertown, MD 21620
Phone: 410.778.4894
Email: letsstay@claddaughbb.com
URL: www.claddaughbb.com
Stately farmhouse, inviting stop for Eastern Shore travelers. Within 5 miles of Chestertown.
Courtyard Inn
Contact: Manager
6336 Church Hill Rd
Chestertown, MD 21620
Phone: 410-778-2755
Email: n/a
URL: na
Just three miles from Chestertown
Great Oak Manor
Contact: Cassandra Fedas
10568 Cliff Road
Chestertown, MD 21620
Phone: 410.778.5943
Email: cassandra@greatoak.com
URL: www.greatoak.com
Elegant Waterfront Manor House with spectacular Chesapeake Bay sunsets off a private beach. Located approximately 10 miles from Chestertown.
Inn at Mitchell House
Contact: Jim and Tracy Stone
8796 Maryland Parkway
Chestertown, MD 21620
Phone: 470.778.6500
Email: innkeeper@innatmitchellhouse.com
URL: www.innatmitchellhouse.com
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
Mears Great Oak Landing
Contact: Manager
22170 Great Oak Landing Road
Chestertown, MD 21620
Phone: 410-778-5007
Email: info@mearsgreastoaklanding.com
URL: www.mearsgreatoaklanding.com
28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
River Inn at Rolph's Wharf
Contact: Innkeeper
1008 Rolph's Wharf Rd
Chestertown, MD 21620
Phone: 800-894-6347
Email: n/a
URL: www.rolphswharf.com
Victorian Farmhouse on the shores of the Chester River. Approximately 3 miles from Chestertown.

Chestertown
Near Chestertown
Galena
Rock Hall
Vacation Rentals

Lodging Near Galena

Kitty Knight House
Contact:
14028 Augustine Herman Highway
Georgetown, MD 21930
Phone: 410.648.5200
Email: restaurant@kittyknight.com
URL: www.kittyknight.com
18th Century Charm in the 21st Century. The Kitty Knight House & Deck feature traditional Eastern Shore cuisine with a historical touch. The Kitty Knight Inn features eleven beautifully appointed rooms.
Rose Hill Farm B&B
Contact: Allison & Greg Bird
13842 Gregg Neck Rd.
Galena, MD 21635
Phone: 410-648-5334
Email: n/a
URL: www.kentcounty.com/lodging
Quiet country B&B on a 100 acre farm
The Carrousel Horse
Contact: Jan Graham
145 North Main Street
Galena, MD 21635
Phone: 410.648.5476
Email: wgraham@verizon.net
URL: www.carrouselhorsebnb.com
Elegant and comfortable Victorian inn within a mile of the Sassafras River yacht marinas

Chestertown
Near Chestertown
Galena
Rock Hall
Vacation Rentals

Lodging In Rock Hall

Bay Breeze Inn
Contact: Jim and Liese Gillin
5758 Main Street
Rock Hall, MD 21661
Phone: (410) 639-2061
Email: crkayak@bluecrab.org
URL: www.baybreezinn.com
Guests savor the unhurried timeless quality of this rural watermen's village where an earlier and friendlier way of life continues to thrive. Guests are invited to enjoy breakfast al fresco on the rear patio or to simply view the garden.
Black Duck Inn
Contact: Kathleen Johnson
21906 Chesapeake Ave.
Rock Hall, MD 21661
Phone: (410) 639-2478
Email: blackduckinn@verizon.net
URL: www.blackduckinn-rockhall.com
Overlooking picturesque Rock Hall Harbor, we offer five comfortable guest rooms and complimentary dockage for overnight guests arriving by boat.
Carriage House
Contact: Mark and Mylita Jacob
5877 Coleman Rd.
Rock Hall, Md 21661
Phone: 410-639-2855
Email: mjacob@mawaterservices.com
URL: www.carriagehousemd.com/
A delightfully intimate hideaway vacation spot in a quaint fishing village near the Chesapeake Bay. Enjoy stunning water views while being close to great restaurants and quaint shops. We are just a hop, skip and a splash from the Public Beach.
Hotel Tallulah's on Main
Contact: Barry Barr & Jim Messersmith
5750 Main Street
Rock Hall, MD 21661
Phone: (410) 639-2596
Email: tallulah@intercom.net
URL: www.tallulahsonmain.com/
Come and relax with us just steps away from fine dining, antique shops, clothing, wine and grocery stores. Each of our five beautiful suites is equipped with cable television, coffee, tea and breakfast bars to get you started in the morning.
Inn at Huntingfield Creek
Contact: Jim and Joanne Rich
4928 Eastern Neck Road
Rock Hall, MD 21661
Phone: (410) 639-7779
Email: huntingfieldcreek@verizon.net
URL: www.huntingfield.com/
A true wildlife habitat at this elegant,four-season farm estate with 1100 ft. of glorious water front. First class accommodations and full country breakfast. Lovely gardens, walking paths and inviting saltwater pool. Pet and family friendly cottages.
Inn at Osprey Point
Contact: Tory Messina
20786 Rock Hall Avenue
Rock Hall, MD 21661
Phone: (410) 639-2194
Email: innkeeper@ospreypoint.com
URL: www.ospreypoint.com/
Elegant lodging and gourmet restaurant on thirty magnificent acres overlooking the water. Osprey Point brings together the charm of colonial Williamsburg with the luxury and convenience of the 21st century.
Moonlight Bay Inn & Marina
Contact: Dottie and Bob Santangello
6002 Lawton Avenue,
Rock Hall, MD 21661
Phone: (410) 639-2660
Email: moonbay@friend.ly.net
URL: www.moonlightbayinn.com/
Moonlight Bay Inn hugs the shore of the beautiful Chesapeake Bay. Whether you are watching the everchanging scenes on the bay or meditating in the English Garden, each view is a painter?s paradise.
North Point Marina - Motel
Contact: NA
5639 Walnut Street
Rock Hall, Md 21661
Phone: (410) 639-2907
Email: npm@dmv.com
URL: www.rockhallmd.com/npoint
Delightfully comfortable bayfront rooms, complete with free sunset, full up-close water view and premium Cable TV! Large, beautifully landscaped in-ground swimming pool, right by the ay!
Old Gratitude House
Contact: Sandy and Hank Mayer
5944 Lawton Avenue
Rock Hall, MD 21661
Phone: 410-639-7448
Email: oldgratitudehouse@verizon.net
URL: www.oldgratitudehouse.com
Waterfront elegance on the Eastern Shore. Start the day with a full gourmet breakfast on the large deck looking out on the Chesapeake Bay; then use our kayaks to explore nearby waterways, and experience a fantastic sunset at day?s end.
Pruitt's Swan Point Inn
Contact: a block or so short of the bay
Coleman Road & Rock Hall Avenue (Rt 20)
Rock Hall, MD 21661
Phone: 410-639-2500
Email: NA
URL: www.rockhallmd.com/swanpointinn/
Light, airy rooms with all of the amenities overlooking Swan Creek, the inn features a fabulous restaurant on the premises.
Spring Cove Manor
Contact: Jim and Liese Gillin
21060 Spring Cove Manor
Rock Hall, MD 21661
Phone: 410-639-2061
Email: crkayak@bluecrab.org
URL: www.springcovemanor.com
A delightfully secluded B & B at water's edge a short distance from the quaint little fishing village of Rock Hall. Luxurious accommodations in delightful seclusion with kayak and sailing adventures at your doorstep.
Swan Haven Bed & Breakfast
Contact: Ron Mansfield
20950 Rock Hall Avenue
Rock Hall, MD 21661
Phone: (410) 639-2527
Email: swanhaven@friend.ly.net
URL: www.swanhaven.com/
Enjoy delightful accommodations on the water, with small boating adventures of many kinds to be had starting right at our docks. Only a short walk to Rock Hall's many fine restaurants and quaint shops.
The Mariner's Motel
Contact:
5681 Hawthorne Ave.
Rock Hall, MD 21661
Phone: (410) 639-2291
Email: rockhall@dmv.com
URL: www.marinermotelmd.com
This landmark motel located across the street from Rock Hall Harbor has been welcoming guests for over 30 years. We are the closest motel to the center of town, yet offer tranquillity and serenity that is hard to find in today's world.

Chestertown
Near Chestertown
Galena
Rock Hall
Vacation Rentals

Vacation Rentals in Kent County

Coveside Cottage
Contact: Liese and Jim Gillin
12060 Spring Cove Road
Rock Hall, MD 21661 21661
Phone: (410) 639-2061
Email: crkayak@bluecrab.org
URL: www.springcovemanor.com/
A fully equipped home for the most discerning guests. This brand-new home-away-from home supplies every amenity one could demand. Two bedrooms, 2 full baths with skylights, a full kitchen, dining nook, living room opening onto a full deck.
Kentfields Farm
Contact: Innkeeper
5793 Quaker Neck Landing Rd
Chestertown, MD 21620
Phone: 410-778-4181
Email: innkeeper@kentfieldsfarm.com
URL: www.kentfieldsfarm.com
A country estate located within 5 miles of Chestertown on the Jarrett Creek.
River House on Moon Bay
Contact:
Learman Road
Chestertown, MD 21620
Phone: 866-398-2722
Email: N/A
URL: www.vrbo.com/90429
A four bedroom waterfront home outside of Chestertown with outstanding views, billards room and more. Available year round for weekly rentals.
Rock Hall Beach House
Contact: Ann Bovee/Mariners Motel
5807 Beach Road
Rock Hall, MD 21661
Phone: 410-639-2291
Email: reservations@marinersmotel.com
URL: www.marinersmotel.com
This two bedroom,1 and 1/2 bath home has large kitchen, dining area and comfortable living room. Launch your kayak from the sandy beach across the street, bike to town or enjoy the sunsets from the screened porch, the Beach House is a perfect fit for everyone on holiday.
Rock Hall Retreat
Contact: Old Gratitude House
21128 Striper Run Rd
Rock Hall, Md 21661
Phone: (410) 639-7448
Email: oldgratitudehouse@verizon.net
URL: www.oldgratitudehouse.com
A three bedroom, two bath home located in a beautiful wooded community in the heart of Rock Hall. Comfortably sleeps six, and is ideal for families looking to get away for a few days or a week. Walk to the harbor and numerous local restaurants.
Stepne Manor
Contact: Innkeeper
406 South Cross Street
Chestertown, MD 21620
Phone: 410-810-1845
Email: n/a
URL: www.kentcounty.com/lodging
Historic Home available for Weekend and Weekly rentals.
Tallulah's on the Beach
Contact: Barry Barr & Jim Messersmith
5783 Beach Road
Rock Hall, MD 21661
Phone: Phone: (410) 63
Email: tallulah@intercom.net
URL: www.tallulahsonmain.com/beach.htm
Watch sailboats by day and the lights of Baltimore by night as you enjoy the sunroom, or visit the beach located just steps from your front door. Complete with comfortable living room, a spacious kitchen, full bath, 2+ bedrooms and air conditioning.
The Overlook on Main
Contact: The Carriage House Inn
5761 Main St.
Rock Hall, Md 21661
Phone: (410) 639-2855
Email: mjacob@wtrsoft.com
URL: www.carriagehousemd.com/overlook.htm
This lovely little get-away with a European flair is convenient to all the amenities of Rock Hall. Two bedroom, one bath, apartment has a master bedroom with private balcony, fully equipped kitchen, spacious living room, and a front balcony overlooking Main St.
The River House
Contact: Jim and Joanne Rich
Inn at Huntingfield Creek
Rock Hall, MD 21661
Phone: (410) 639-7779
Email: innkeepers@huntingfield.com
URL: www.huntingfield.com/riverhouse.asp
A spacious waterfront 4 bedroom house, located 4 miles down the road from the Inn. Well-furnished with spectacular views of Church Creek and Chester River. Perfect for family gatherings. Pet-friendly and very private. Rented with or w/o Inn privileges.

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