Vacation Rentals By Owner In Rock Hall, MD

Showing 20 Of 57 Vacation Rentals

$405.98

Bayside Cottage steps from Rock Hall Harbor

Rock Hall, Maryland, United States

Welcome to our charming bayside cottage, just steps away from Rock Hall harbor, Bayside Landing Park, and waterfront restaurants.brbrThis 3 bedroom, 1.5 bath house is a cute and cozy space to spend time making memories with family and friends. The large yard offers a spacious area for outdoor games, a bistro set to enjoy your morning coffee, and a large picnic table under a majestic Holly tree.brbrWe also provide bikes which can be used for exploring town or heading down to Ferry Park Beach.

Bed

Bath

Sleeps

Exceptional(41)

$1119.63

/ Nightly

Private Vacation Home

Sunset Lodge on the Bay

Rock Hall, Maryland, United States

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.

Bed

Bath

Sleeps

Exceptional(6)

$226.44

/ Nightly

Apartment

Cute waterfront apartment -- 8 min from the beach!

Rock Hall, Maryland, United States

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.

Bed

Bath

Sleeps

Exceptional(9)

$254.04

/ Nightly

Private Vacation Home

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

Rock Hall, Maryland, United States

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.

Bed

Bath

Sleeps

Exceptional(3)

$309.17

/ Nightly

Private Vacation Home

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

Rock Hall, Maryland, United States

Welcome to the Cottage on N. Main St. brYour home away from home located on a quiet street and peaceful at night. This 3 bedroom 1 bath sleeps 5. Newly renovated with Coastal and Nautical decor. A short walk to local shops, Bayside Foods, Fresh Start, ATM's, Java Rock coffee shop, The scoop ice cream, The Mainstay for live music, Rock Hall liquors and Restaurants. 5 min drive to Sandy beach at Ferry Park to watch incredible sunsets, swim and relax. You are minutes away from waterfront restaurants Waterman's Crab House and Harbor Shack which have live bands on the weekends. Enjoy a drink at Admirals Club Beach Bar with amazing views and games. Sail with Blue Crab Chesapeake Charters and visit East Neck Island for hiking, bird watching and fishing. Enjoy a day trip at Chestertown, MD.

Bed

Bath

Sleeps

Exceptional(3)

$273.35

/ Nightly

Private Vacation Home

Rock Hall Retreat w/ Balcony Near Park & Marina!

Rock Hall, Maryland, United States

Experience comfort and tranquility at this 3-bedroom, 2.5-bath vacation rental in Rock Hall, MD! Perfect for families, this charming home features a furnished balcony for sipping your morning coffee, a fully equipped kitchen for preparing delicious homemade meals, and easy access to the Rock Hall Community Park next door. When you're ready to venture out, consider riding the provided bicycles around town or exploring the Eastern Neck National Wildlife Refuge. Your getaway awaits!brbr-- THE PROPERTY --brbrWalk to Rock Hall Community Playground | Near Rock Hall Harbor | Quiet LocationbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin BedsbrbrINDOOR LIVING: Smart TV, dining table, beverage refrigerator (2nd floor), board games, ceiling fansbrKITCHEN: Keurig & French press coffee makers (coffee & sugar provided), cooking utensils, dishware & flatware, dishwasher, ice maker, microwave, toaster, water filterbrOUTDOOR LIVING: Furnished balcony, deck, yard, playground viewsbrGENERAL: Free WiFi, keyless entry, central air conditioning & heating, hair dryer, hangers, in-unit laundry machines, linens/towels, trash bags/paper towels, clothes steamer, bicyclesbrACCESSIBILITY: 2-story home, exterior steps to enter, bedroom & bathroom on 1st floorbrFAQ: Quiet hours (10:00 PM-7:00 AM)brPARKING: Driveway (1 vehicle), carport (1 vehicle)brbr-- THE LOCATION --brbrOUTDOOR SPOTS: Rock Hall Community Park & Playground (0.4 miles), Rock Hall Landing Marina (1 mile), Eastern Neck National Wildlife Refuge (6 miles), Tolchester Beach & Marina (7 miles), Mitchell Bluff (8 miles)brHOT SPOTS: The Mainstay (0.5 miles), Caulk's Field Monument (6 miles), Chestertown (14 miles), Wilmer Park (14 miles), Chester River Yacht & Country Club (14 miles)brLOCAL EATS: Java Rock Coffee House & Cafe (0.5 miles), Waterman's Crab House (0.9 miles), Harbor Shack (1 mile)brAIRPORT: Baltimore/Washington International Thurgood Marshall Airport (77 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 27 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires exterior steps to enter. While there is a bedroom on the 1st floor, an additional interior staircase is required to access the remaining bedrooms on the 2nd floorbr- NOTE: Please observe quiet hours from 10:00 PM to 7:00 AM

Bed

Bath

Sleeps

Exceptional(7)

$311.18

/ Nightly

Private Vacation Home

3 min walk to the Bay, restaurants and shopping!

Rock Hall, Maryland, United States

Newly renovated, a 3 min. walk to the popular restaurants/marina and shopping. 3 Bedroom/ 2 Bathrooms, Central A/C, Smart Tvs in every room; Your log in is required. 1 King Bedroom, 1 Queen Bedroom, 1 Queen Sleeper sofa & 2 Full beds upstairs with new 2nd Floor bathroom. Linens/towels provided. Fully stocked Kitchen, Gas grill/charcoal grill, lighted Patio. Front porch for people watching.

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Bath

Sleeps

$268.18

/ Nightly

Private Vacation Home

BAYSIDE BUNGALOW

Rock Hall, Maryland, United States

Lovely bayside Bungalow on a quiet street on Swan Creek with an indoor dry Swedish sauna and views of the cheseapeake Bay.brPrivate entrance. Bikes and beach chairs provided. Microwave and small refrigerator

Bed

Bath

Sleeps

Exceptional(3)

$376.3

/ Nightly

Private Vacation Home

Walking distance to restaurants and marinas...dog-friendly!

Rock Hall, Maryland, United States

Unwind in this charming 3-bedroom dog-friendly home in Rock Hall, just one block off of the harbor and within walking distance to several restaurants and marinas. brbrThere are two bedrooms on the first floor, one with a queen bed and one with two twins, and a full bath. With a separate suite on the 2nd floor (one king, one daybed, and full bath) and extra sleeping space in the living room (queen sofa bed), this home is suited for a two-family vacation. brbrBed linens, bath and beach towels, pillows, hair dryers and makeup mirrors are provided plus a starter kit with toilet paper, paper towels, trash bags, hand soap, dishwashing liquid and dishwasher pods. brbrEnjoy crabs on the back deck under the lighted umbrella, prepare your fresh catch (bait freezer in shed!) on the propane grill, and play cornhole in the fenced backyard. The well-furnished kitchen features a Wolf range, full size refrigerator, microwave, dishwasher, Keurig and 12-cup coffee makers, and a uniquely crafted island with barstools. Adjacent to the kitchen is an enclosed utility area with a full size washer and dryer, and a dining area with a sliding door to the back deck. brbrWith internet/Wi-Fi, guest-controlled air conditioning/heat, and a gas fireplace in the living room for cooler nights, you have everything you need for your relaxing Eastern Shore escape.

Bed

Bath

Sleeps

Exceptional(2)

$660.45

/ Nightly

Private Vacation Home

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Rock Hall, Maryland, United States

Forget your worries in this spacious and serene waterfront property with expansive Privacy and Fabulous water views of the Chesapeake Bay.brbrEscape the hustle and bustle of the city. Its a 2 hour drive to DC or Philadelphia. Feel the stress wind down as you enjoy this serene retreat while viewing boat traffic on the Chesapeake Bay. Don't miss one of the best sunsets!brbrThis property features 4 bedrooms and 3 full bathrooms. The primary suite has a king bed and ensuite bathroom. There is a bedroom with 2 queen beds and another with a queen. There is a full bathroom nearby. In the back of the house there is a large bunk room with 2 sets of bunk beds and a queen bed just outside is a 2nd living room with a kitchenette. Along with a full bathroom. Perfect for the kids to enjoy or your inlaws.brbrWith open concept living and dining areas there is plenty of room for all. Outside, is a lovely deck with outdoor dining area, BBQ grill, and lounge chairs. Take in the natural beauty of your surroundings. There is a firepit, perfect to tell those tale tales while enjoying each others company.brbrThis home is perfect for families or group get aways. There are multiple entertainment areas and plenty of space for an unforgetable stay overlooking the Chesapeake Bay.

Bed

Bath

Sleeps

Exceptional(17)

$448.63

/ Nightly

Private Vacation Home

Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD

Rock Hall, Maryland, United States

Charming, spacious home with modern updates in a lovely town on the Chesapeake Bay. brNew air conditioning/heating system, updated appliances, Smart TV, comfortable beds, and tasteful decorating all enhance your visit. brAt Great Blue Heron House enjoy Eastern Shore living while visiting the Waterman's Town of Rock Hall. brBlue Heron restaurant is one block away and Carriage House - a delightful place to have weekend breakfasts during the summer - is across the street to the right! Go left and take a short stroll to the lovely, colonial restaurant of Osprey Point. brWalk two blocks to the town beach on the Bay. Swim in the Bay or sit and enjoy the views all the way to Annapolis! Enjoy gorgeous sunsets at the beach each evening!brGreat Blue Heron House is next door to Blue Heron Park where many birds can be spotted. A marina is at the end of the quiet side street. brTake a sunset sail after a day at the beach. It is easy to reserve spots on a sailing charter that leaves from Waterman’s dock. brExplore the trails of Eastern Neck Wildlife Island or rent kayaks to enjoy being on the water. brTaste local, delicious steamed crabs either at one of the waterfront restaurants or on your back deck while you enjoy the scenery of the spacious yard! brBring your bike, rent bikes, take the Tram, walk, or take a drive and explore the town of Rock Hall. brDo some shopping in town and treat yourself to lunch, ice cream, or sweets at the town stores.brGreat Blue Heron House is a special place to enjoy a vacation with family or friends!

Bed

Bath

Sleeps

Exceptional(98)

$467.26

/ Nightly

Private Vacation Home

Stay in the landmark Lighthouse!

Rock Hall, Maryland, United States

3 BR 3 Bath w/Elevator providing easy access to all 3 floors. Wrap-A-Round 3rd Floor deck providing 360 degree panoramic view of Swan Creek and Blue Huron Park. Relax in the spacious Great Room while viewing the newly installed 55 curved screen TV. Enjoy 2 master bedrooms on 2ed Floor offering the same views as above. Larger front Master Bedroom offering bath with handicap friendly features. Eat in the large European style kitchen or dine out at any one of the numerous fine dining establisments located near by. Property located within walking distance of several local marinas offering answers to all your boating needs including Rock Hall Public Beach. brNewly refreshed landscaping making for a picturest setting. Come and enjoy a delightful get-a-way.

Bed

Bath

Sleeps

Exceptional(133)

$408.85

/ Nightly

Cottage

Eastern Shore beach cottage get-away

Rock Hall, Maryland, United States

Recently renovated, charming cottage. A sandy beach is right across the quiet street from the cottage. The sandy bottom goes way out in the shallow water--great for kids, playing and launching kayaks. The cottage looks west to the amazing sunsets. Mr./Ms. Blue Heron visits the beach regularly and the ospreys dive for breakfast for their babies. Watch the crabbing boats ply the waters offshore as you enjoy your morning coffee and the amazing sunsets in the evening from the living room, dining room, or lawn chairs.brbrRock Hall, MD is a quaint fishing village on the upper Eastern Shore in Kent County. Rock Hall is on Southern Living's 2016 list of Best Small Town's of the South. Kent County is the least populated county in MD, so it is a true get-away. Only one blinking traffic light in Rock Hall. There are also many marinas (sailing and motor boats), about 8 at last count. A surprisingly wide choice of restaurants and entertainment (including live entertainment at the Mainstay & local restaurants) is available. Biking is great as the roads have wide, paved berms and wind throughout the rural, country-side. The Eastern Neck Island Wildlife Refuge is a short drive away and provides wonderful bird-watching, or go crabbing on the docks and bridges on the way. Kayaking, fishing and boating opportunities abound. Chestertown, home of Washington College, with its many restaurants, shops and activities is 10 miles away.brbrThe cottage will be cleaned and disinfected in accordance with VRBO guidance between each guest. brbrPLEASE NOTE: The service fee listed in the charges goes to VRBO/HomeAway, NOT to the owner. VRBO/HomeAway is also collecting it in the first payment request which you will receive. brbr

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Bath

Sleeps

$388.5

/ Nightly

Private Vacation Home

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

Rock Hall, Maryland, United States

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!

Bed

Bath

Sleeps

Exceptional(2)

$416.86

/ Nightly

Private Vacation Home

Brand New Modern Rock Hall home with Water Views

Rock Hall, Maryland, United States

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!brbrWe have 2 paddle boards, a kayak and a canoe for guests to use as well as several bikes and beach chairs.

Bed

Bath

Sleeps

Exceptional(37)

$387.39

/ Nightly

Private Vacation Home

Serene Waterfront Cottage with dock and gorgeous views.

Rock Hall, Maryland, United States

Egret's Nest is a charming waterfront cottage located on Gray's Inn Creek with access to the Chesapeake Bay. Drive up an elegant tree lined path and enter paradise! This gorgeous two story Victorian has stunning views from the living room and Master bedroom. Sip wine or morning coffee from the balcony or enjoy dinner on the screened porch. Take a stroll onto your private dock with use of 4 seater paddle boat and/or 2 kayaks. Fish right off your pier.

Bed

Bath

Sleeps

Exceptional(29)

$261.22

/ Nightly

Private Vacation Home

Overton Farm Cottage

Rock Hall, Maryland, United States

Newly renovated waterfront cottage. Everything in this home is new! We are located next to Eastern Neck National Wildlife Refuge. It is a very 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. You have unlimited use of TWO private docks for your own boat, kayak, or paddle board. A 16 foot rowboat is also available at the property for in season use (May 15-Oct 1)! There are beautiful waterfront restaurants nearby as well as a beach in Rock Hall. Towels and linen provided.

Bed

Bath

Sleeps

Exceptional(13)

$288.85

/ Nightly

Private Vacation Home

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Rock Hall, Maryland, United States

We are pleased to welcome you to enjoy our newly established home away from home! Whether you are a family or a couple, a group of friends, a boater, fisherman, hunter, or just some one who wants to step back to a slower pace of life, we hope you love Rock Hall as much as we do in this quiet 3-story getaway. Nothing beats a morning coffee in the hammock chair with the birds’ symphony all around you in the tall pines. Home is located just a half mile or so walk to the bay. Rock Hall is perfect for boating, paddle boarding, kayaking, birdwatching & biking. brWi-Fi & 75” SmartTV in the living room to enjoy the game or a family TV night. Sleeps up to 7, in possibly 8, dining table for 8. Convenient e-locks. Able to accommodate responsible pet owners with hypoallergenic (non-shedding) dogs only. Parking for three vehicles. Kitchen is well-stocked with the basics & outside grill is ready to go . (No parties please as this is located in a development and attached on one side). Property is euipped with a Ring video doorbell at front door.

Bed

Bath

Sleeps

Exceptional(1)

$354.22

/ Nightly

Private Vacation Home

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

Rock Hall, Maryland, United States

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!

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Bath

Sleeps

$334.56

/ Nightly

Cottage

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Rock Hall, Maryland, United States

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 to yourselves from 11-5 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 private 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.

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Most popular vacation rentals in Rock Hall

$369.23

/ Nightly

Private vacation home

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$354.22

/ Nightly

Private vacation home

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

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$361.86

/ Nightly

Private vacation home

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$315.61

/ Nightly

Private vacation home

Waterfront at \"The Landing\" in Historic Rock Hall, overlooking marina and pool.

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$241.43

/ Nightly

Apartment

Knot's Landing, spacious Apt. downtown Rock Hall

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$555.00

/ Nightly

Private vacation home

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

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$271.34

/ Nightly

Cottage

Blissful Retreat In Rock Hall

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$311.18

/ Nightly

Private vacation home

3 min walk to the Bay, restaurants and shopping!

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$376.30

/ Nightly

Private vacation home

Walking distance to restaurants and marinas...dog-friendly!

Rock Hall, Maryland, United States

Bed

Bath

Sleeps

$271.24

/ Nightly

Cottage

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Rock Hall, Maryland, United States

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Sleeps

Vacation Rentals By Owner In Rock Hall, MD

$405.98

$1119.63

$226.44

$254.04

$309.17

$273.35

$311.18

$268.18

$376.3

$660.45

$448.63

$467.26

$408.85

$388.5

$416.86

$387.39

$261.22

$288.85

$354.22

$334.56

Most popular vacation rentals in Rock Hall

$369.23

$354.22

$361.86

$315.61

$241.43

$555.00

$271.34

$311.18

$376.30

$271.24

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