Vacation Rentals By Owner In Rock Hall, MD

Nestled in Rock Hall, this delightful cottage is a perfect retreat for guests. With 1 cozy bedroom, AC, WiFi, and heating, this brilliant space offers everything you need for a terrific stay. We're happy to assist with any questions while you stay at our cottage.brbrThis charming 2 story cottage with spacious bedroom upstairs and comfortable living room down is a rare gem. You get the pool as a shared pool each day. Parking for 1 car. Sorry, no friends allowed to visit as the pool is for your use only.brThe pool has lovely gardens surrounding it along with comfortable lounge chairs. The cottage is just in front of the pool in the private back yard. Downstairs is seating for relaxing, a mini refrigerator and a full bathroom with a tub and a shower. Upstairs a spacious room with a king bed and TV. There is one parking place just outside the gate to the cottage and pool. Great getaway in the heart of Rock Hall.brbrCharming Cottage with shared pool use centrally located in the quaint town of Rock Hall while the pool is open from May 1 until Sept. 21 the cottage is available year round.

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Rock Hall, Maryland, United States

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$388.5

Welcome to your private waterfront retreat in Rock Hall, Maryland! Nestled along the serene shores of the Greys Inn Creek, this charming getaway offers breathtaking water views, stunning sunsets, and access to the bay. Whether you're looking to relax, explore, or enjoy the area's famous seafood, this is the perfect spot for your next escape.brbrA private setting overlooking water on 2 sides. Come by water or by land. There is a private pier to tie up a boat or use one of the kayaks which we provide. The pier is perfect for fishing or crabbing and there are plenty of outdoor seating to just watch your peaceful surroundings. brbrThe first floor has a comfortable living room with a smart TV overlooking the waterfront. An open kitchen which is well equipped. Dining room table for 6 and a recently remodeled full bathroom. There are 2 bedrooms on the first floor. The bunk room has a queen on the bottom and a twin above along with another twin bed. The second bedroom has a queen bed.brbrUpstairs there is a large space with a full bed and a twin along with another smart TV.brbrOutside overlooking the waterfront, there is a hammock, lots of seating to enjoy a good book or to play games. Enjoy Eastern Shore Living!

Heron Cove, a Waterfront vacation spot near Rock Hall with private pier

Rock Hall, Maryland, United States

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Exceptional(21)

$220.84

You will be close to everything in Rock Hall when you stay at this centrally-located ground-level apartment. Just 1 block from Main Street, park the car and walk to everything Rock Hall - shops, marinas, grocery store, ice cream store, events, and more. A full kitchen, comfortable living room, private entrance and backyard access await you. Large grassy yard - great for BBQ, games, outdoor dining. Sleeps 4 comfortably.

Apartment

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall, Maryland, United States

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Sleeps

Exceptional(4)

$738.78

Rock Hall, fondly known as the “Pearl of the Chesapeake,” sits right on the shores of the Chesapeake Bay, where the pace slows and the sunsets steal the show. Right in the heart of town on Main Street, Bay Breeze Inn is a gracious circa 1884 home that blends historic charm with relaxed coastal living.brbrDesigned for gathering, the home offers generous indoor and outdoor spaces that make it ideal for holidays, weddings, reunions, and memorable weekends with friends and family. The main house comfortably sleeps 13, while a separate Carriage House in the rear (1 King and 1 Twin) is also available for additional accommodations.brbrInside, guests will find a full kitchen, a large dining room for shared meals, a cozy fireside sitting room, and a spacious living room. Outdoors, the property invites you to linger with a large rear patio with automatic awning, a garden and firepit area, plus multiple decks including a second floor deck with awnings and a third floor perch for fresh bay breezes.brbrFrom the front porch, you have a front row seat to the charm of Main Street, where festivals, music, and small town parades pass by throughout the year. Off street parking is available in the rear, and the Chesapeake Bay, marinas, and many of Rock Hall’s beloved restaurants are just a short walk away.brbrAdding to the experience, Main Wine, a cozy neighborhood wine bar, is located right on the premises. And when the day winds down, Rock Hall’s legendary sunsets over the Chesapeake remind you exactly why this little town is called a pearl

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall, Maryland, United States

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Exceptional(41)

$2191.02

Heated pool, hot tub, boat dock, and sauna!br5 acres of unobstructed Chesapeake Bay views and complete privacy. Surrounded by farmland but only 2 miles from restaurants & shops. br9 bedrooms including 5 bedrooms on the ground level.brLaunch provided kayaks easily into the Chesapeake Bay.brRide bikes and jog on the serene country roads.brSports room, with two 65” TVs, a poker table, pool table, and foosball table.brOutdoor fire pit, 2 gas fireplaces, 3 wood-burning fireplaces.br3 kitchens, 2 living rooms - plenty of room for the whole family!brDining room that seats 20 guests. brEnormous living room complete with an 80-inch TV, breathtaking sunset views of the Chesapeake Bay and Bay Bridge, and two-story glass windows. brVery family-friendly, with many kid-friendly amenities provided, many books and games provided.brBeds for up to 28 guests. brCome enjoy the Chesapeake Bay in serene luxury!brbrHot tub & sauna open year-round brHeated pool open mid-April through end of October brbrPlease message us beforehand if you would like to book an event as there is an additional charge, thank you!

Villa

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall, Maryland, United States

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Exceptional(5)

$404.63

Just two hours from the Philadelphia or DC metro area, you will find the Bay Beach Oasis. Less than a 5 minute walk to public beach access with sunsets over the Chesapeake Bay, use of paddle boards with kayak seats, and several nearby restaurants with fresh seafood. Three bikes available to ride to the adorable Main Street shopping and cafes. Depending on the season, harvest your own fruits and vegetables from our plentiful gardens. Come, relax, make new memories, and have a little fun!

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Rock Hall, Maryland, United States

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Exceptional(24)

$1258.26

Stunning waterfront property in Rock Hall. Expansive outdoor space with large pool and long pier on picturesque Swan Creek, with easy access to the Bay. The house features a chef’s kitchen and sun-filled rooms with fantastic water views. Great for an extended family or group. brbrRecently featured in Conde Nast Traveler as one of the Best Vacation Rentals in the World! https://www.cntraveler.com/gallery/the-best-airbnbs-and-vacation-rentals-in-the-worldbrbrThe house and property truly sit on the water’s edge, creating a wonderful on-the-water atmosphere. This is relatively rare among Chesapeake properties as regulations require that homes sit back at least 100 feet from the water. This house’s close proximity is grandfathered in.brbrThe property includes a large saltwater pool as well as a canoe and kayaks for boating on Swan Creek. Enjoy basketball in the pool or on the recently installed outdoor half-court hoop. Ample lawn space to play games from corn hole to badminton to spike ball. Or simply sit outside and enjoy the beautiful water views as you watch a nesting osprey or boats sailing to the nearby marina. The house includes a 300 foot pier. Cruiser bikes offer the chance to ride into town or explore the nearby area. brbrFor those who like to cook, the house features a light-filled kitchen with a Sub Zero refrigerator and Dacor range. And for those who like to eat, the house includes multiple dining options - a large dining room, a screened in porch, as well as an outdoor patio. brbrFor the occasional rainy day, enjoy games, large screen tv, fiber optic broadband or ping pong or foosball in the large 4 car garage. brbrGround floor Master BR includes a king bed, with an attached bathroom that includes a jacuzzi. brbrThe second floor includes 4 BR with 2 bathrooms. BR1 has a queen bed, BR 2 - queen, BR 3- full, and BR 4 - two twins and a futon for 2.brbr1 mile walk/bike to the charming town of Rock Hall. Short drive to the Saturday Farmer’s Market in Chestertown, or to the beautiful Eastern Neck Wildlife Preserve. Tennis courts are available in the Rock Hall town park. There are multiple options in Rock Hall for fishing charters on the BaybrbrFull amenities include: washer drying, fiber optic broadband and wifi, central AC, and more.brbrbr

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Rock Hall, Maryland, United States

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Exceptional(7)

$241.43

Welcome to Knot's landing - a spacious apartment located above one of Rock Hall's favorite shops in the quaint Main Street corridor. Steps outside of your front door you will find a coffee shop, sweets / bakery shop, farmers market, ice cream, and more! Use the provided bicycles for quick access to other restaurants and marinas. Perfect place to stay to enjoy Rock Hall, Chestertown, and surrounding Kent County.

Apartment

Knot's Landing, spacious Apt. downtown Rock Hall

Rock Hall, Maryland, United States

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Exceptional(37)

$266.33

Welcome Aboard to our adorable 3 Bedroom Duplex in a quiet community within walking distance to waterfront marinas and restaurants. This home has 3 bedrooms and sleeps up to 7 people. 4 Legged friends welcome!! Full Kitchen, Dining area, Family room with Fireplace. Front porch with sitting chairs. Enjoy the historic town of Rock Hall from this Central location!

Entire Townhouse in Rock Hall

Rock Hall, Maryland, United States

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Exceptional(65)

$711.15

This waterfront 4 BR, 2 1/2 BA Private house in the town of Rock Hall has been recently renovated. Its newest addition is an outdoor Hot Tub, perfect for a weekend getaway or week long vacation. Enjoy watching the sailboats going by while enjoying a relaxing evening. Fun in all seasons. Or in the summer months take a dip in the pool. Decking and railings have been remodeled to give an expansive view of the water. It has 300' pier with 4' MWD in Swan Creek, a private pool and the best sunsets to enjoy on the deck or with cocktails relaxing under the shade trees. Kayaks, bikes and more are provided for your entertainment. Walk or bike to town and enjoy restaurants and shops. A great property for a family vacation off the Chesapeake Bay.brbrCheck us out on Instagram @ontherocksrockhallbrbrThe spacebr“On the Rocks” is a waterfront property with 300’ pier on Swan Creek with 4-5’ MLW. Located in the heart of Rock Hall. Bike, walk, or drive to restaurants and shops in the Waterfront town of Rock Hall. The above ground 4' deep pool is great for the kids, or big kids to enjoy. Lots of yard space to play games such as corn hole or just relax in a lounge chair. Enjoy fabulous sunsets from the house or sitting in an Adirondack chair on the pier. You're welcome to tie your boat up at the dock and it can be launched easily at a nearby public landing or you may arrive by boat. Fishing and crabbing can be done from the dock, or venture out in a Kayak and explore Swan Creek or Tavern Creek. Recently added electric fireplaces in living room and master BR.brOne well behaved dog is welcome with a $125 pet fee, please ask.brbrGuest accessbr4 Bedrooms, 2 1/2 baths + an outside shower. Central a/c. Pool on site along with use of 300’ pier. Hot Tub, Kayaks, bikes, and other outdoor items for your use.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Rock Hall, Maryland, United States

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Exceptional(22)

$355.1

Easy walk to everything in Rock Hall - The beach, the marinas, restaurants, bars and shops. 15 minute drive to historic Chestertown. Large rooms with plenty of common space to relax. First floor wheelchair accessible suite. Two zone central AC. New kitchen, baths, beds, floors and paint 2022. Sit on the front porch and watch all the other happy people walk and pedal by.brbrHere's a review from a guest with a handicapped child: brbrGreat property. Very clean. My daughter is in a wheelchair and I have rented houses that state they are wheelchair accessible in the past only to find they actually are not. This house was 100% wheelchair accessible. My daughter had a great time and was able to easily move around the first floor. The hosts are great as well. Very good with communication and very gracious. Would stay again!brbrDate of arrival - June 20, 2025

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Rock Hall, Maryland, United States

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Exceptional(44)

$1119.63

A waterfront estate set apart from the rest, offering something unique that’s hard to find on Maryland’s eastern shore. Sunset Lodge offers a refreshing new twist on how to vacation! We are a privately owned 58-acre estate located on the Chesapeake Bay offering a private beach, stunning waterfront views and picturesque sunsets every evening. This estate provides the ultimate tranquility and privacy that is hard to find. A long, secluded driveway leads the way to a large house sitting just yards from the water's edge. brbr This newly updated 5,000 square foot house has 7 large windows facing the bay, providing waterfront views from both ends of the house. There are 6 spacious bedrooms, including two master bedrooms. An open floorplan takes you from the kitchen and dining area to the living room and onto a spacious porch, extending the living space for entertainment or the ultimate place to relax. For entertainment the game room has a pool table, TV and board games. The bar room provides extra comfy seating for our guests, with a TV and views to die for. Other favorite past times are eating locally caught steamed crabs, taking walks along the beach, collecting sea glass, swimming in the bay, relaxing and watching the regattas pass by in front of a captivating sunset. brbrThe town of Rock Hall, known as the “Pearl of the Chesapeake”, made “Southern Livings” Best of the South Small Towns list. This historic waterman’s town, established in 1706, is an exceptional place to experience the bay for crabbing, fishing, hunting, bird watching and boating. brbrThis private waterfront getaway on the Eastern Shore is only 3 miles from town where you can stroll Main Street, explore the unique shops, go on a self-guided waterman’s tour, enjoy the live entertainment, check out the Farmers and Artisans Market (in season) or bike to Eastern Neck Island National Wildlife Refuge, a birdwatchers delight and home to bald eagles and migratory birds.. brbrDon’t miss this opportunity to experience something different, come be our guest.

Sunset Lodge on the Bay

Rock Hall, Maryland, United States

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Exceptional(65)

$249.75

Bayside Beach House was named House of the Week! Check it out: brbrProfessionally built vacation rental with charm and comfort! This 2 bedroom, 1 1/2 bath cottage is steps from the sandy beach featuring shallow, calm waters and fantastic sunsets.brbrThe cottage is fully equipped with a fabulous kitchen, WiFi, cable TV, and washer-dryer. Linens and bath towels are included. The first floor main bedroom features a queen size bed with pillow top mattress. The upstairs bedroom is home to a full size bed, half bath, and lounge area with DirecTV. The outdoor areas feature a back deck with grill, table with umbrella, and an upstairs balcony with a peak of the water - perfect for your morning coffee or evening cocktail.brbrBayside Beach House is located steps from the Chesapeake Bay and is perfect for a couple's retreat, a family vacation, a girls/guys weekend away, or a writer or artist who needs some peace and quiet.brbrFeel free to check out our other property outside of St. Michaels, Maryland VRBO Listing #599767

Brand New Cottage Steps from the Beach!

Rock Hall, Maryland, United States

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Exceptional(130)

$282.13

In the delightful town of Rock Hall lies a snug two-bedroom cottage, ideal for your upcoming getaway. As you step inside, you'll be greeted by a fully stocked kitchen, complete with a refrigerator, grill, microwave, and all the essentials you need to prepare delicious meals. Unwind in the comfortable living room, or step outside and enjoy the fresh air on the porch, surrounded by outdoor furniture. brbrIndulge in the property's top traveler favorites, such as the inviting hot tub, free WiFi, and cozy fireplace. Explore the nearby Rock Hall Harbor, just a 5-minute drive away, or venture to Washington College, a 24-minute drive from the cottage. brbrWith amenities like air conditioning, heating, linens, and a hair dryer, you'll have all the comforts of home during your stay. Enjoy the convenience of on-site parking and an EV car charger for electric vehicles. Whether you're looking to relax by the pool or enjoy a movie night with the satellite/cable TV, this cottage has everything you need for an unforgettable vacation.

Blissful Retreat In Rock Hall

Rock Hall, Maryland, United States

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Sleeps

Exceptional(21)

$453.25

Welcome to Sailors Crossing! Your home away from home. Short walk to Main St, harbor and restaurants. Next to tennis and basketball courts, and a playground for the little ones. Or watch the incredible sunsets from the beach. Plenty of room for family or friends to get together. Sleeps 10. First floor bedroom has a queen bed. Four rooms on the 2nd fl. include large bonus room with TV, games and twin beds. Enjoy fresh air on the screened in porch or play lawn games in the spacious back yard.

Sailors Crossing

Rock Hall, Maryland, United States

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Exceptional(18)

$260.85

Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or long term 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 miles). Large mud room and laundry area. Sunroom provides additional room for guests (with a pull out bed). Spacious fenced in backyard (with open land behind) or front deck is perfect for an afternoon cocktail. Large driveway to place a boat trailer and park your vehicle.brbrGarage is being used as secured owner storage and is unavailable for use.

In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!

Rock Hall, Maryland, United States

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Exceptional(9)

$226.44

An adorable carriage house with panoramic views overlooking Swan Creek, located on a private road. Nature lovers and bird watchers would have a grand time here, with frequent Bald Eagles sightings during winter/spring, ospreys and many other waterfowls, birds by your window in summer. Centrally located: 3 blocks from town beach, restaurants across the road and Rock Hall downtown within walkable distance, next to two local marina. Your private dock through Blue Heron Marsh to Swan Creek.

Apartment

Cute waterfront apartment -- 8 min from the beach!

Rock Hall, Maryland, United States

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Exceptional(74)

$952.75

This breathtaking property, located on 12 acres, is perfect for a vacation rental, weekend getaway, wedding venue, event venue, and so much more. Newly renovated and appointed waterfront home boasts stunning waterfront views and sunsets overlooking the Chesapeake Bay. An open layout includes the living room and flowing kitchen with a sunroom and wrap around porch, extending the living space to an entertainers delight or the ultimate place to unwind. A warming fireplace is the heart of the home, centered in the middle of the house, creating a fabulous gathering area for all to enjoy.brbrPlease refrain from moving the furniture. If you do, kindly return it to its original position. Thank you!brbrMain floor contains 3 bedrooms, including master suite with sliding door accessing deck with bay view, and 2 bathrooms with walk in showers.br Pool with large patio and pool house with screened in area, half bath, refrigerator, and counters for entertaining. brBasement with separate entrance is complete with 3 bedrooms, full kitchen and bathroom, laundry and pool table. brBayfront patio complete with fire pit for roasting marshmallows/smores and enjoying the sunsets.brSome of our guests favorite past times here are eating locally caught steamed crabs, taking walks along the beach, collecting sea glass, swimming in the bay, relaxing and watching the regattas pass by in front of a captivating sunset.brThe town of Rock Hall, known as the “Pearl of the Chesapeake” made the magazines “Southern Livings” Best South Small Towns list. This historic waterman’s town established in 1706 is an exceptional place to experience the bay for crabbing, fishing, hunting, bird watching and boating.brThis private waterfront getaway on the Eastern Shore is only 3 miles away from town where you can stroll down Main Street, explore the unique shops, go on a self-guided waterman’s tour, enjoy the live entertainment, check out the Farmers and Artisans Market at Rock Hall Village in the center of town or bike to Eastern Neck Island, and an amazing National Park to where the bald eagles resides.br

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall, Maryland, United States

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$326.34

Rock Hall - Voted as one of the 10 best towns in Maryland for many years.brbrThere is a Holiday and special event supplemental cost for some designated events.brbrIn Oysterman Cottage you can stay the week or two days in a quaint cottage with Chesapeake Bay View of the harbor from 20982 Bayside Avenue in Rock Hall, MD. Rock Hall is known as the Pearl of the Chesapeake an unspoiled waterfront town on the Eastern Shore of the Chesapeake Bay. It has been voted consistently by Maryland Life as the best sunrise and sunset on the bay. It offers magnificent harbors, many fine marinas, over 2,000 boat slips, a broad spectrum of lodging facilities and restaurants, as well as, a host of recreational opportunities. You can walk to Waterman's Crab House, or Harbor Shack restaurant or drive to enjoy Flying Decoy Bar and Grill, Blue Heron Oyster House, JavaRock, Pearl on Main and Osprey Point Inn and Restaurants. Perhaps take an easy drive to Chestertown for the Kitchen at the Imperial Inn. Chestertown has additional downtown shopping.brbrKent County and Rock Hall guide use this link: https://www.kentcounty.com/media/tourism/visitors_guide/ brbrRock Hall 2025 Events (not a complete listing), check local info for specific datesbrMay 10 Garden Club plant salebrMay 23-25 Chestertown Tea PartybrMay 31-June1 Rock Hall TriathlonbrJune 6-8 Rock Hall Volunteer Fire Company Fishing Tournamentbr July 3-4 July 4th celebration with fireworks on July 3brJuly 6 Kent County Watermans DaybrAug 8-10 Pirates & Wenches EventbrbrSeptember 27-29 Waterman's Triathlon FestivalbrbrRock Hall Fireworks are scheduled each July 3rd.brThis is a 35-minute show choreographed to patriotic music. It can be viewed from the bay and from anywhere in Rock Hall Harbor.brbrRock Hall is a quaint seashore town with a thriving fishing and boating community. The harbor is filled with crab and oyster boats which leave early every morning, returning with heaving baskets of shellfish for the town's fresh seafood restaurants. The main town too is lovely, with two large 18th century mansions on the National Register of Historic Places, three museums which discuss the town's local heritage and the maritime industry, and many picturesque board houses. The town is particularly stunning at sunset, when the warm light envelops the town and harbor in an intense glow.brbrThe Cottage: Our smoke-free cottage has been completely redone, with new furniture, double shower/double sink bath and laundry room. A new back deck was recently. Enjoy our new granite counters and kitchen flooring. It is enjoyed by family and friends and since our move to North Carolina, and has welcomed selected guests.brbrTwo bedrooms (one queen, two twins) and a sleeping porch with pull out queen sofa-bed offers various sleeping arrangements.brbrNew 42 Flat Panel Samsung Smart TV all streaming service with 100+ channels + YouTube with local Baltimore & Washington channels, Netflix + all other streaming services included.brbrOwner supplies all linens, coffee and laundry items. brbrWe supply Internet and there is also free internet service at the Java Rock Coffee house in the center of town, a great breakfast and lunch stop.brbrPet fee is per pet of $150.00 We have pet rules for your review and acceptance. brbrWe will send you our pet policies before billing. Thanks for your understanding.brbrKeywords: House

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Rock Hall, Maryland, United States

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Most popular vacation rentals in Rock Hall

$329.63

Waterfront in Historic Rock Hall, overlooking the main harbor and Chesapeake Bay

Rock Hall, Maryland, United States

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$403.63

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall, Maryland, United States

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$403.30

Eastern Shore beach cottage get-away

Rock Hall, Maryland, United States

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$374.98

Brand New Modern Rock Hall home with Water Views

Rock Hall, Maryland, United States

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$363.58

Bayside Cottage steps from Rock Hall Harbor

Rock Hall, Maryland, United States

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Sleeps

$355.10

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Rock Hall, Maryland, United States

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Sleeps

$333.00

200 steps to the beach!

Rock Hall, Maryland, United States

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$278.48

Rock Hall Retreat w/ Balcony Near Park & Marina!

Rock Hall, Maryland, United States

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$282.13

Blissful Retreat In Rock Hall

Rock Hall, Maryland, United States

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$285.86