Accommodations

Kent County has an eclectic mix of accommodations to appease the most discriminating guest. A cottage overlooking an historic beach town, a restored Colonial-era inn, a 19th-century farmhouse bed-and-breakfast set within a working vineyard, or a marina cottage surrounded by boats; you will find the perfect place to stay in Kent County.

A Simple Stay

208 Mount Vernon Avenue
Chestertown, MD 21620
410-778-4359


Two allergy-friendly rooms in a cozy 1947 Cape Cod - a minute's walk from Washington College. "The soul should always stand ajar," [ready to welcome] - Emily Dickinson
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Bay Breeze Inn

5758 North Main Street
Rock Hall, MD 21661
410-639-2061
chesterkayak@yahoo.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.
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Bay View Beach House

5783 Beach Road
Rock Hall, MD 21661
410-639-2596
tallulah@intercom.net

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.
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Bayshore Campground

4228 Eastern Neck Road
Rock Hall, MD 21661
410-639-7485
camping@bayshorecamping.com

Bayshore Campground is located on the Chesapeake Bay in Rock Hall Maryland, where we offer a beautiful and unique vacation location. Accommodations with water and electric hook-ups available. Come enjoy our peaceful and relaxing atmosphere for all.
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Bayside Retreat

21017 Bayside Avenue
Rock Hall, MD 21661
410-639-2291
reservations@marinersmotel.com

Bayside Retreat has 3 bedrooms and 1 1/2 baths and is located a short walk away from great restaurants on the harbor. Guests also enjoy pool privileges at Rock Hall Landing Marina just 50 yards away.
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Black Duck Inn

21906 Chesapeake Avenue
Rock Hall, MD 21661
410-639-2478
bdi.lodging@theblackduckinn.com

Overlooking picturesque Rock Hall Harbor, we offer five comfortable guest rooms and complimentary dockage for overnight guests arriving by boat.
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Brampton Bed and Breakfast Inn

25227 Chestertown Road
Chestertown, MD 21620
410-778-1860
innkeeper@bramptoninn.com

Discover a historic and award-winning bed and breakfast in Chestertown, MD. This romantic inn is situated on 35 beautiful acres with glorious views and delicious breakfasts! Unforgettable rooms offer whirlpool tubs, fireplaces, and flat-screen TVs.
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Brittland Manor

800 High Street
Chestertown, MD 21620
410-810-7591
nturner@brittlandestates.com

From fields to rivers Brittland Estates personifies elegance in a rural setting. Our collection of heritage properties are near historic Chestertown and are ideal for weddings, family reunions, corporate events and get-aways.
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Carriage House

5877 Coleman Road
Rock Hall, MD 21661
410-639-2855
mylita@muskratalley.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.
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Cottage On Kent

400 North Kent Street
Chestertown, MD 21620
443-480-0658
cottageonkent@yahoo.com

Cottage On Kent is a charming guest cottage rental. It is located within walking distance to downtown, the Chester River and Washington College.
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Courtyard Inn

6336 Church Hill Road
Chestertown, MD 21620
410-778-2755



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Coveside Cottage

12060 Spring Cove Road
Rock Hall, MD 21661
410-639-2061
crkayak@bluecrab.org

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.
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Crow Vineyard, Winery & Inn

12441 Vansant Corner Road
Kennedyville, MD 21645
410-648-5687
crowfarmmd@gmail.com

Enjoy a unique farm experience: walk the trails on our 365 acre farm, enjoy views of the vineyard, experience a wine tasting, stay in our Inn...about an hour from Philadelphia, Baltimore, Washington DC, minutes from Chestertown.
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Edesville House

5727 South Hawthorne Avenue
Rock Hall, MD 21661
410-639-2291
reservations@marinermotelmd.com


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Elizabeth's Pond Retreat

6426 Elizabeths Lane
Rock Hall, MD 21661
310-370-1281
RockHallVacationRentals@gmail.com

Just six minutes from the town of Rock Hall and 13 minutes from Chestertown, this completely renovated home on 5 mostly wooded acres features a large pond right in the back yard. 3 bedrooms and 2 1/2 baths, sleeps 6 - 8–
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Great Oak Manor

10568 Cliff Road
Chestertown, MD 21620
410-778-5943
info@greatoakmd.com

Elegant 12 room waterfront manor house with enchanting sunsets over the Chesapeake Bay on Maryland's Eastern Shore.
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Haven Point Inn and Gallery

20748 Rock Hall Avenue
Rock Hall, MD 21661
410-639-4184
havenpointinn@gmail.com

Haven Point Inn & Gallery is a new contemporary inn and gallery with beautifully appointed rooms designed with your comfort in mind. A complimentary delicious gourmet breakfast will help you start your day.
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Holiday Inn Express

150 Scheeler Road
Chestertown, MD 21620
410-778-0778


Modern convenience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary.
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Inn at Haven Harbour

20950 Rock Hall Avenue
Rock Hall, MD 21661
410-778-6697
inn@havenharbour.com

Conveniently located within a short (5 min) walking distance of the main town of Rock Hall and adjacent to the resort amenities of Haven Harbour Marina, the Inn at Haven Harbour exudes the nautical luxury and charm of a boater's paradise.
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Inn at Huntingfield Creek

4928 Eastern Neck Road
Rock Hall, MD 21661
410-639-7779
huntingfieldcreek@verizon.net

A true wildlife habitat at this elegant, four-season farm estate with 1100 ft. of glorious waterfront. First class accommodations and full country breakfast. Lovely gardens, walking paths and inviting saltwater pool. Pet and family friendly cottages
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Inn at Mitchell House

8796 Maryland Parkway
Chestertown, MD 21620
410-778-6500
innkeeper@innatmitchellhouse.com

Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
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Inn at Osprey Point, Marina, and Restaurant

20786 Rock Hall Avenue
Rock Hall, MD 21661
410-639-2194
devon@ospreypoint.com

At Osprey Point Inn, Restaurant and Marina, you'll experience the perfect fusion of luxurious accommodations, elegant dining, and a relaxed and friendly environment.
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InnTowne House

21309 East Sharp Street
Rock Hall, MD 21661
410-639-7779
huntingfieldcreek@verizon.net

Upscale, modern and new two bedroom apartment overlooking Main St. in Rock Hall. Wonderful amenities, lots of space and full kitchen. $275 per night. Up to four guests. Two night minimum, weekly rates available. Includes breakfast at Java Rock.
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John L. Stam House

114 Washington Avenue
Chestertown, MD 21620
410-708-8059
jlstamhouse@gmail.com

Gothic Revival Victorian, fully restored. Full breakfast and afternoon tea. Within blocks of the Historic District of Chestertown.
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Kitty Knight Restaurant & Inn

14028 Augustine Herman Highway
Galena, MD 21635
410-648-5200
info@kittyknight.com


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Lodging at the Imperial

208 High Street
Chestertown, MD 21620
410-778-3001
kate@lodgingattheimperial.com

Lodging at The Imperial is a small owner-operated hotel in the heart of the Chestertown historic district. We are the only hotel in town with a pub and a fine dining restaurant.
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Mears Great Oak Landing

22170 Great Oak Landing Road
Chestertown, MD 21620
410-778-5007
info@greatoakmd.com

28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
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Moonlight Bay Inn & Marina

6002 Lawton Avenue
Rock Hall, MD 21661
410-639-2660
innkeeper@moonlightbayinn.com

Come by car or by boat. 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.
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North Point Marina

5639 Walnut Street
Rock Hall, MD 21661
410-639-2907
northpointmarina@verizon.net

Delightfully comfortable bay-front 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!
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Pilot House

20880 Rock Hall Avenue
Rock Hall, MD 21661
410-778-6697
email@havenharbour.com

Pilot House is a full house rental at the Inn at Haven Harbour.
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Quality Suites

160 Scheeler Road
Chestertown, MD 21620
410-810-0555


Modern conveniences with 53 rooms. Close to Chestertown's Historic District.
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River Lodge

219 Britland Farm Lane
Chestertown, MD 21620
410-810-7591
info@BrittlandEstates.com

With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination.
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Rock Hall Landing Mariners Motel

5681 South Hawthorne Avenue
Rock Hall, MD 21661
410-639-2291
dockmaster@rockhalllanding.com

Clean, comfortable accommodations overlooking beautiful Rock Hall harbor. Pool & play area. Well behaved dogs welcome.
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Rolph's Wharf, The River Inn

1008 Rolphs Wharf Road
Chestertown, MD 21620
410-778-6347


Spend a night – or a weekend – in charm and comfort. With views of the Chester River and the adjoining farm, the River Inn at Rolph’s Wharf offers you the opportunity to spend a relaxing night or two away from the everyday. Each of the rooms has its
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Secret Garden on Main

5764 North Main Street
Rock Hall, MD 21661
443-465-0681



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Sharp Street Retreat

21236 East Sharp Street
Rock Hall, MD 21661
310-370-1281
RockHallVacationRentals@gmail.com

This charming home on Sharp Street in Rock Hall is a perfect place to stay for you and your family and friends. This recently renovated house sleeps 10 comfortably..
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Spring Cove Manor

21020 Spring Cove Road
Rock Hall, MD 21661
410-639-2061
info@springcove.us

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.
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Stepne Manor

406 South Cross Street
Chestertown, MD 21620
410-810-7591
info@BrittlandEstates.com

This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.
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Sunset Lodge

4480 Eastern Neck Road
Rock Hall, MD 21661
410-639-7846
Info@sunsetlodgeonthebay.com

58-acre estate located on the Chesapeake Bay with a personal beach, offering stunning waterfront views and sunsets. Only 3 miles away from town and Eastern Neck Island.
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Swan Creek Waterfront

20997 Haven Road
Rock Hall, MD 21661
410-708-5589
dianeoliver98@gmail.com

Swan Creek Waterfront Cottage with large yard leading to 200'+ pier for boats, crabbing, and fishing. Explore the quaint town of Rock Hall with nearby restaurants, shopping and loads of outdoor activities.
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The Beach Cottage

5791 Beach Road
Rock Hall, MD 21661
410-708-5589
dianeoliver98@gmail.com

Beach Front Cottage Get-A-Way Newly renovated, charming cottage with a sandy beach right across the quiet street. Beach is great for swimming, kayaking or just gazing at the boats passing by in the distance. Amazing Chesapeake Bay sunsets in the quai
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The Beach Place

5783 Beach Road
Rock Hall, MD 21661
410-639-2596
tallulah@intercom.net


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The Lodge on Main

5718 North Main Street
Rock Hall, MD 21661
310-370-1281
RockHallVacationRentals@gmail.com

Everything is crisp, clean and recently renovated. It sleeps up to 9 in three bedrooms and offers 2 full baths. The completely efficient kitchen offers an overlook on Main Street.
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The White Swan Tavern, Colonial Inn

231 High Street
Chestertown, MD 21620
(410) 778-2300
info@whiteswantavern.com


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Thornton Estate

10618 Perkins Hill Road
Chestertown, MD 21620
N/A


Elegance and seclusion on 300+ acres - Thornton Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificient manor house anchors the 325 acre preserved farm minutes outside of Chestertown, MD.
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Welcome Aboard

5813 Clam Cove
Rock Hall, MD 21661
610-246-9387
rockhallrental@gmail.com

Welcome Aboard is a 3 bedroom and 2 1/2 bath home in Rock Hall's Harbor Woods Community. A short walk to Main Street attractions and waterfront dining. Includes Wi-fi, linens, fully equipped kitchen, BBQ, and laundry. Fireplace in living room.
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