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.

108 Annex

108 South Mill Street
Chestertown, MD 21620
718-687-7588
mariannaandstephen@gmail.com
http://airbnb.com/h/chestertown-guesthouse

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer.
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114 High Street Vacation Rental

114 High Street
Chestertown, MD 21620
443-480-6331
booking@114high.com
http://www.114high.com

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200 High Street

202 High Street
Chestertown, MD 21620
202-607-6762
jsantoboni@me.com
https://www.airbnb.com/h/202highchestertown

Bright and open 2 bedroom apartment in the heart of downtown Chestertown
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Bay Breeze Inn II

5758 North Main Street
Rock Hall, MD 21661
410-639-2061
susan.f.mckeown@gmail.com
http://BayBreezeInn2.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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Bayshore Campground

4228 Eastern Neck Road
Rock Hall, MD 21661
410-639-7485
camping@bayshorecamping.com
http://www.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 Cottage

21007 Bayside Avenue
Rock Hall, MD 21661
443-752-0500
baysidecottagerentals@gmail.com
https://www.vrbo.com/4124797?dateless=true

A block off of Rock Hall harbor, Bayside Cottage is a dog-friendly, 3BR/2BA home with a deck, grill, fenced yard, AC, internet/Wi-Fi, fireplace and driveway parking. Walk to restaurants/marinas.
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Bayside Retreat

21017 Bayside Avenue
Rock Hall, MD 21661
610-952-4535
reservations@marinermotelmd.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
http://www.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
https://bramptoninn.com/?utm_source=KentCounty

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

205 Cannon Street Suite 1
Chestertown, MD 21620
443-282-0860
info@brittlandestates.com
http://www.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
http://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.
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Circa 1865

13738 Still Pond Road
Still Pond, MD 21667
410-708-1525
thestillpondinn@gmail.com

The Still Pond Inn is a beautiful 1865 farm house with secure entry. Two 3-room suites and one queen room. All rooms feature large screen, streaming TVs, and free Wi Fi. Suites have additional sitting rooms, all rooms and all bathrooms havewalk-in showers
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Comfort Inn & Suites

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

https://www.choicehotels.com/maryland/chestertown/comfort-inn-hotels/md364

Modern convenience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary.
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Cottage On Kent

400 North Kent Street
Chestertown, MD 21620
443-480-0658
cottageonkent@yahoo.com
http://www.cottageonkent.org

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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Coveside Cottage

12060 Spring Cove Road
Rock Hall, MD 21661
410-639-2061

http://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.
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Crow Vineyard, Winery & Inn

12441 Vansant Corner Road
Kennedyville, MD 21645
302-304-0551
crowfarmmd@gmail.com
http://www.crowfarmmd.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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Downtown Apartment

112 North Queen Street
Chestertown, MD 21620
202-415-0820
kvielmo@gmail.com

1 Bedroom Apartment 2 blocks from downtown Chestertown MD on a quiet residential street with one queen size bed.
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Evergreen Knoll Cottages

130 1st Avenue
Betterton, MD 21610

evergreenknoll46@gmail.com
https://sites.google.com/view/evergreen-knoll/home

Secluded Waterfront Vacation Cottages
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Great Oak Manor

10568 Cliff Road
Chestertown, MD 21620
410-778-5943
welcome@greatoakmanor.com
https://www.greatoakmanor.com

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Haven Point Inn and Gallery

20748 Rock Hall Avenue
Rock Hall, MD 21661
410-639-4184
havenpointinn@gmail.com
http://www.havenpointinn.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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Inn at Haven Harbour

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

A premier Chesapeake Bay resort destination located in Rock Hall, Maryland. Explore our six buildings, 22 well-appointed guest rooms and suites, full-house vacation rental, pet-friendly accommodations and countless amenities.
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Inn at Huntingfield Creek

4928 Eastern Neck Road
Rock Hall, MD 21661
410-639-7779
huntingfieldcreek@verizon.net
http://www.huntingfield.com/

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
http://www.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
dteat@ospreypoint.com
http://www.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
http://www.huntingfield.com

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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Kitty Knight Inn

14028 Augustine Herman Highway
Galena, MD 21635
410-648-5200
info@kittyknight.com
https://www.kittyknight.com/inn

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North Point Marina

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

20804 Rock Hall Avenue
Rock Hall, MD 21661
410-778-6697
email@havenharbour.com
http://www.Havenharbour.com

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Red Roof Inn & Suites

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

https://www.redroof.com/property/md/chestertown/RRI1268

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

219 Britland Farm Lane
Chestertown, MD 21620
443-282-0860
info@BrittlandEstates.com
https://www.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 Marina & Motel

5657 South Hawthorne Avenue
Rock Hall, MD 21661
410-639-2224
gm@rockhalllanding.com
https://www.sagamoreblue.com/marinas/rock-hall-landing/rock-hall-landing-marina

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Rolling View Farms, LLC

110 Elm Street
Chestertown, MD 21620
410-320-0852
timjgough@aol.com
https://airbnb.com/h/110elmst

Please consider staying with us when visiting historic Chestertown. Our five year young Rancher is ideally located within walking distance to Washington College and downtown. This fully equipped home offers the perfect getaway.
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Rolph's Wharf, The River Inn

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

http://rolphswharfmarina.com/the-river-inn/

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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Ruby's Sea Glass Cottage LLC

303 Ericsson Avenue
Betterton, MD 21610
443-480-3219
rubysseaglasscottage@yahoo.com

Vacation Rental House in Betterton, MD
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Safe Harbor Great Oak Landing

22170 Great Oak Landing Road
Chestertown, MD 21620
410-778-5007
info@greatoakmd.com
http://www.mearsgreatoaklanding.com

28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
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Sharp Street Retreat

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

21060 Spring Cove Road
Rock Hall, MD 21661
410-639-2061
info@springcove.us
http://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.
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Stepne Manor

406 South Cross Street
Chestertown, MD 21620
443-282-0860
info@BrittlandEstates.com
https://www.brittlandestates.com/copy-of-river-lodge-accommodations

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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Still Pond Properties, LLC

12445 Coopers Lane
Worton, MD 21678
302-259-1644
info@stillpondretreat.com
https://www.stillpondretreat.com/

Short Term Rental Waterfront Studio Apartment
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Sunset Lodge

4480 Eastern Neck Road
Rock Hall, MD 21661
410-639-7846
Info@sunsetlodgeonthebay.com
http://www.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 Bay Break

4728 Huntingfield Road
Rock Hall, MD 21661
434-409-9902
thebaybreak@gmail.com
https://www.houfy.com/lodging/stunning-8-bedroom-villa-on-the-chesapeake-bay/61619

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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 Blissful Retreat

20389 Humphreys Point Road
Rock Hall, MD 21661
410-639-7074
barbiharms@gmail.com
https://www.airbnb.com/rooms/32692291?source_impression_id=p3_1562707330_QS0MaDPCiAfHuX27

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The Lodge on Main

5718 North Main Street
Rock Hall, MD 21661
310-370-1281
RockHallVacationRentals@gmail.com
http://www.rockhallvacationrentals.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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Thornton Estate

10618 Perkins Hill Road
Chestertown, MD 21620
N/A

http://thorntonestate.com/

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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Tipsea Crab

21053 Striper Run
Rock Hall, MD 21661
410-708-5589
mannunziato@msn.com
http://vrbo.com/3857426

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Washington College Conference Services

300 Washington Avenue
Chestertown, MD 21620
410-778-7253
egrant2@washcoll.edu
https://www.washcoll.edu/people_departments/offices/conference-services/index.php

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Welcome Aboard

5813 Clam Cove
Rock Hall, MD 21661
443-494-8044
clamcovebookings@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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White Swan Tavern

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

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