Vacation rentals in Rock Hall

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

The Blissful Retreat @theblissfulretreat

Serene space nestled in the woods; with water views. You have your own private cottage on our 10 acre property to watch the sunsets and enjoy the nature all around. You'll spot deer, bunnies, frogs, turtles, birds and so much more from the lovely front porch! As a Nurse I can guarantee our space has always been cleaned and sanitized to the highest standards, regular use of a ozone light. Check us out on insta for more blissfulness - theblissfulretreat and FB- theblissfulretreatrockhall

Overton Farm Cottage

Newly renovated waterfront cottage. We are located next to Eastern Neck National Wildlife Refuge. It is an exclusive and private location. Located on an Eastern Shore Farm. 2 bedroom, 2 bathroom cottage that sleeps 4. No children under 12. No Smoking or pets. Towels & linen are provided. Unlimited use to 2 private docks for your own boat, kayak, or paddle board. There are beautiful waterfront restaurants nearby as well as a beach in Rock Hall. Row boat provided in season (May 15-October 1).

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

Anchor Down

Welcome to our new construction home in Rock Hall, MD—where the water is calm, the pace is slower, and is a perfect place to unwind. With 3 cozy bedrooms, 2 sparkling bathrooms, and ample parking for boats or RVs, it’s perfect for families, friends, or solo adventurers. Enjoy small-town charm, water activities, fast Wi-Fi, and a stocked kitchen. Pack your bags and embrace Rock Hall’s relaxed vibe—our home’s got heart and plenty of room to make memories. Book now!

Traveler Guest Suite @ Cinnamon By The Bay

The Traveler offers a private bedroom. private bath with shower, and fully equipped eat-in kitchen. For those guests who prefer separation from their dining area, but don’t need a separate living space, Traveler is a perfect match. Easy walking distance to Rock Hall's shopping, coffee shop, restaurants, music venue, and festivities. Pet-friendly for an additional fee with easy access to the community back deck and rear yard.

Chesapeake Bay Retreat W/Breathtaking Views

Escape to a waterfront retreat on the Chesapeake Bay with sweeping water views, vaulted ceilings, and expansive windows that fill the home with natural light. Located minutes from Rock Hall and historic Chestertown. Recently refreshed for the season with updated layout, window tinting for comfort, and a newly added pool table. Perfect for blue crab season, relaxing getaways, and exploring Maryland’s Eastern Shore.

Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

Bay Beach Oasis

Just two hours from the DC metro area, Philadelphia, or Baltimore, you will find the Bay Beach Oasis. A 3 minute walk to public beach access with sunsets over the Chesapeake Bay. Beach chairs, SUP boards, and several nearby restaurants with fresh seafood. Three bikes available to ride to the adorable Main Street shopping and cafes. Come, relax, make new memories, and have a little fun!

Historic Cottage | 1min DT | Views | W/D | Parking

Newly updated ✔ Beach essentials ✔ Sunset views ✔ ☞ Screened-in front porch ☞ Fully equipped + stocked kitchen ☞ Bose Bluetooth sound system ☞ 250 Mbps wifi ☞ Onsite washer + dryer ☞ Parking → driveway ☞ Dedicated workspace ☞ 43” smart TV 3 mins → Beaches + marinas ⛱ 1 mins → DT Rock Hall (cafes, dining, shopping)