Eastern Shore Holiday Rentals, Maryland: Private House Rentals

A marina with numerous boats docked at wooden piers under a clear sky.

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Go beyond your typical stay in Eastern Shore

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Our top choices for Eastern Shore hotels

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

1. Best Western Plus Easton Inn & Suites

Easton

Raheem

Rp2.309.487

Rp2.540.436 total

includes taxes & fees

29 Sept - 30 Sept

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

A gym with a treadmill, elliptical, and stationary bike.

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

2. Baymont by Wyndham Easton

Easton

Ellen

Rp1.772.397

Rp1.949.636 total

includes taxes & fees

29 Sept - 30 Sept

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.

3. Holiday Inn Express Easton by IHG

Easton

Emily

Rp2.399.002

Rp2.638.902 total

includes taxes & fees

25 Oct - 26 Oct

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.

A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

4. The Tidewater Inn

Easton

Miriam

Rp3.383.667

Rp3.722.033 total

includes taxes & fees

27 Oct - 28 Oct

A lobby with seating, a reception desk, and a cityscape mural on the wall.

A swimming pool with a blue interior, surrounded by lounge chairs and a changing area.

A hotel room with a bed, a sofa, a small table, a TV, and a framed picture on the wall.

A spacious indoor area with multiple seating options including tables and booths, a bar area with a cityscape mural, and large windows providing natural light.

5. La Quinta Inn & Suites by Wyndham Newark - Elkton

Elkton

Gregory

Rp1.849.738

Rp2.071.706 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a bed, bedside table, lamp, TV, wardrobe, and a mirror.

A laundry facility with four washing machines, a ventilation system, and a door.

A spacious lounge area with a sectional sofa, a round table, and a green armchair. There is a reception desk in the background with a small plant on it.

A building entrance with glass doors, a bench, and a sign that reads "STRONGER PACKS STICK TOGETHER".

6. Red Roof Inn Perryville

Perryville

Jawan

Rp1.343.450

Rp1.504.664 total

includes taxes & fees

1 Oct - 2 Oct

A multi-story hotel with a covered entrance, wheelchair-accessible parking, and a stone facade.

A hotel room with two beds, a desk, a window with curtains, and a blue headboard.

A reception area with a blue accent wall, a wooden reception desk, and a flat-screen monitor.

A modern dining area with a long table and chairs, a kitchen area with a yellow backsplash, and a refrigerator.

7. Microtel Inn & Suites by Wyndham Salisbury

Salisbury

James

Rp1.682.882

Rp1.884.828 total

includes taxes & fees

29 Sept - 30 Sept

A modern lobby with a reception desk, seating area, and artwork on the walls.

A hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.

A hotel room with a bed, a sofa, a TV, a desk, and a large window.

8. Best Western Plus Pocomoke City

Pocomoke City

alexis

Rp2.267.415

Rp2.539.503 total

includes taxes & fees

30 Sept - 1 Oct

A swimming pool with a blue ceiling, a sun lounger, and a small table with chairs.

A compact hotel room with a brown sofa, a small wooden table, a kitchenette with a microwave, and a bed.

A hotel room with two green armchairs, a desk with a laptop, a ceiling fan, and large windows offering a view of trees and a road.

A hotel bathroom with two sinks, a large mirror, and a vanity with a TV.

9. Comfort Inn & Suites North East

North East

John

Rp1.775.799

Rp1.988.895 total

includes taxes & fees

19 Oct - 20 Oct

A hotel room with a bed featuring a blanket with "THE RESERVE INN" text, two pillows with a swan design, and a bedside table with a phone.

A bathroom with a white sink, a mirror, and a towel rack with multiple towels.

A hotel named "The Reserve Inn" with a prominent sign, a lobby entrance, and Coca-Cola vending machines.

A coffee station with a coffee maker, disposable cups, sugar, and creamer.

10. The Reserve Inn

Salisbury

Beth

Rp1.449.964

Rp1.623.981 total

includes taxes & fees

29 Sept - 30 Sept

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.

A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

A modern lounge area with seating, a fireplace, and a television.

11. Comfort Inn & Suites Chestertown

Chestertown

Amy

Rp1.873.370

Rp2.079.440 total

includes taxes & fees

25 Oct - 26 Oct

A self-service breakfast station with a coffee machine, yogurt dispensers, and a variety of food items.

12. Home2 Suites By Hilton Salisbury Fruitland

Fruitland

Joseph

Rp2.069.945

Rp2.318.339 total

includes taxes & fees

26 Oct - 27 Oct

A lobby with a curved floor, a reception desk, and seating areas.

A buffet with various food items, including omelets and baked goods, displayed in metal trays.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a counter.

A conference room with rows of chairs, a podium, and a Holiday Inn Express sign.

13. Holiday Inn Express & Suites Elkton - University Area by IHG

Elkton

Eleni

Rp2.291.584

Rp2.566.574 total

includes taxes & fees

5 Oct - 6 Oct

A modern lobby with a blue sofa, yellow armchairs, a white coffee table, and a patterned rug.

A pool area with lounge chairs and tables, a tiled pool, and blue walls with windows.

A hotel room with two beds, a desk, a chair, and a large window.

A breakfast bar with a chalkboard wall displaying the word "EAT" and various food-related drawings. There are signs indicating dietary needs and caution for hot surfaces.

14. Hampton Inn Salisbury

Salisbury

Matthew

Rp1.893.779

Rp2.121.033 total

includes taxes & fees

18 Oct - 19 Oct

A modern lobby with a reception desk, a seating area with a sofa and a plant, and a staircase leading to an upper level.

A modern kitchen with dark wood cabinets, a microwave, a coffee machine, and a breakfast bar with a glass display case.

A hotel with a swimming pool, lounge chairs, and a covered outdoor seating area.

A hotel room with a bed, a TV mounted on the wall, a desk with a lamp, a sofa, and a window with curtains.

15. Wingate by Wyndham Salisbury MD Airport North

Salisbury

Frank

Rp1.567.408

Rp1.827.001 total

includes taxes & fees

4 Oct - 5 Oct

A multi-story hotel with a brick facade, large windows, and a covered entrance area.

A hotel room with a bed, a sofa, a dining table, and a window with curtains.

A vending machine stocked with various beverages and snacks, including Pepsi, Mountain Dew, and Doritos.

A modern hotel lobby with a round table, grey armchairs, a flat-screen TV, and a fireplace.

16. Microtel Inn & Suites by Wyndham Ocean City

West Ocean City

Harry

Rp1.354.362

Rp1.722.771 total

includes taxes & fees

30 Sept - 1 Oct

A multi-story hotel with a pool area, balconies, and a view of the ocean.

A lobby with green sofas, a round table with a plant, and a lantern.

A hotel room with a large bed, two chairs, a desk, and a view of the city through the window.

A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.

17. Grand Hotel Ocean City Oceanfront

Downtown Ocean City

Chris

Rp1.235.307

Rp1.383.545 total

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a bed, a TV on a wooden dresser, a sofa, and a window with curtains.

A multi-story hotel with balconies, a swimming pool, and a parking lot.

A multi-story building with a rooftop pool, balconies, and a parking area.

A bathroom with a sink, mirror, cabinet, and toilet.

18. Beachcomber

North Ocean City

Jason

Rp1.260.013

Rp1.768.279 total

includes taxes & fees

29 Sept - 30 Sept

A spacious lobby with a reception desk, seating area, and a television screen.

A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

19. Comfort Inn & Suites Cambridge

Cambridge

Dana

Rp2.073.346

Rp2.301.414 total

includes taxes & fees

27 Oct - 28 Oct

An indoor water park with multiple slides, a water fountain, and seating areas.

An indoor play area with climbing structures, artificial trees, and a sign reading "Howlin' One."

A spacious lobby with a large stone fireplace, modern seating, and large windows with forest views.

A restaurant with multiple tables and chairs, a sign reading "Campfire Kitchen", and a large tree in the center.

20. Great Wolf Lodge Perryville

Perryville

Benningrace

Rp3.335.329

Rp3.735.569 total

includes taxes & fees

18 Oct - 19 Oct

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Holiday Rentals in Eastern Shore

Cottage

A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

A single-story house with a covered porch, a small front yard, and a visible address number.

A modern kitchen with a built-in TV, bar stools, and a herringbone-patterned floor.

A modern living room with a grey sofa, a painting on the wall, and a view of the outside deck.

Shore Point Cottages

Berlin

"Easy accessible"

Apartment

A beach with waves crashing onto the shore.

A kitchen with wooden cabinets, a white refrigerator, a microwave, a stove, and a sink.

A room with a large window overlooking a beach and the sea.

A hotel room with a large bed, wooden floor, two bedside tables with lamps, and two framed pictures on the wall.

Saint Tropez

North Ocean City

"Great place to stay at definitely worth it"

Apartment

A room with two single beds, a window with blinds, a wall-mounted compass picture, and a bedside lamp.

A sign for Ocean Terrace Apartments with a contact number.

A living room with a blue sofa, a wooden coffee table, a dining table with chairs, and a lamp.

Ocean Terrace Family Apartments

Downtown Ocean City

"There isn’t a lot if parking for the property but besides that it was great"

Aparthotel

A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

A large hotel with multiple floors, a central tower, and a body of water in front.

A spacious lobby with a marble floor, a central staircase, and arched windows.

A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a balcony with blue curtains.

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Midtown Ocean City

"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"

Condo

A balcony with a view of a parking lot and buildings.

A spacious living room with a light blue sectional sofa, a wooden coffee table, and a kitchen area in the background.

A kitchen with wooden cabinets, a black refrigerator, a dishwasher, and a granite countertop.

An indoor swimming pool with clear water, a 3 ft depth marking, and a covered area with chairs.

Americana Condos 10th street

Downtown Ocean City

"Wonderful views and so big!"

Apartment

A living room with two grey sofas, a coffee table, and a ceiling fan.

A living room with a grey sofa, patterned cushions, a potted plant, and a view of a building outside.

A dining area with a table set for four, surrounded by grey upholstered chairs. A black wire basket is placed on the table.

A bedroom with a bed, a nightstand, a floor lamp, a ceiling fan, and a door leading to another room.

Cambridge Apt in Walkable Neighborhood

Cambridge

"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"

Apartment

A room with a large bed, multiple windows, and a ceiling fan.

A living room with a television on a wooden stand, a sofa, two armchairs, a coffee table, and a painting on the wall.

A dining area with a table and chairs, a ceiling fan, and a view through a large window.

A spacious living area with a round glass table, two sofas, a bookshelf, and a large painting.

Salisbury Riverfront Lofts

Salisbury

"Excellent choice for the price, recommended for larger groups."

Cabin

A natural water body with ducks swimming, surrounded by greenery and trees.

A bathroom with tiled floors, a shower area with patterned curtains, and a towel rack.

A bunk bed room with wooden walls and a sloped ceiling.

Strawberry Crossroads

Pittsville

"Host was great, very friendly and welcoming. Can fish, grill, and relax. There were goats and chickens which was cool. Overall very peaceful and relaxing."

Aparthotel

A modern living room with a large TV, a sofa, a coffee table, and a view of the sea.

A modern living room with a blue sofa, a small table, a TV, and a view of the sea through large windows.

A modern kitchen with wooden cabinets, a granite countertop, and a dishwasher.

A multi-story hotel with balconies, a view of the ocean, and a sunset in the background.

Bay Club Resort by Coolvacay

Midtown Ocean City

"Room was excellent and the bay view beautiful.."

Condo

A view from a balcony with a striped awning, overlooking a beach with a wooden fence and benches.

A bedroom with a large bed, a wardrobe, a ceiling fan, and a window with curtains.

A living room with a sofa, armchairs, a dining table with chairs, and a TV mounted on the wall.

A kitchen with white cabinets, a stove, a microwave, and a sink.

OCHG VIRGINIA LEE

Downtown Ocean City

"Love the quaintness of the property. Very clean. Needs updating however did have the old school beach vibe. Really enjoyed our stay. "

Apartment

A compact living space with a sofa, a small round table, a kitchenette, and a dining area.

A multi-story building with a balcony, a sign indicating 'ELHARBOUR APTS 1002', and a 'RESERVED' parking sign.

A bedroom with a bed, a nightstand, a lamp, a ceiling fan, and a framed picture on the wall.

A covered porch with a wooden railing, a window with blinds, and a sign reading "Harbour Apt. 1002".

OCHG Bel Harbour Unit 1

Downtown Ocean City

"This was in a great location, we were able to walk to the beach and boardwalk easily."

Aparthotel

A boardwalk with shops, benches, and street lamps.

A balcony with a clear view of the beach, featuring a table and chairs.

A beachside promenade with a view of the ocean, benches, and a sign indicating a beachside restaurant.

A modern kitchen with white cabinets, a stove, and a view of a balcony with a pool.

Boardwalk One

Downtown Ocean City

"We really enjoyed our stay at Boardwalk One! The room was spacious, clean, and comfortable, and the staff made us feel very welcome. We especially loved the location, being right on the boardwalk close to all attractions and shops. We’d happily stay here again!"

Condo

A multi-story hotel with balconies and a sandy beachfront area.

A living room with a blue sofa, two side tables with lamps, a wooden coffee table, a ceiling fan, a television, and a large mirror on the wall.

A bedroom with two beds, a ceiling fan, a TV, a dresser, and a window with blinds.

A small kitchen with white cabinets, a white refrigerator, a wooden table with four white chairs, a lamp, and a life preserver on the wall.

Breakaway East 109

North Ocean City

"Breakaway east is right on the beachfront an are very nice inside. Staff was great as well. Overall in short review my experience was excellent"

Apartment

A living room with a flat-screen TV, two round tables, a sofa, and a ceiling fan.

A room with a wooden table and four chairs, a framed picture on the wall, a wooden cabinet, and an air conditioning unit by the window.

A dining area with a table and chairs, a framed artwork on the wall, and a view into another room with a TV and seating.

Waterfront Gem < 1 Mi to Dtwn Cambridge!

Cambridge

Condo

A coastal residential area with multi-story houses, a parking lot, and a view of the ocean.

A bedroom with a bed, nightstands, a dresser, a ceiling fan, and a window with blinds.

OCHG Townhouse 102 10

Downtown Ocean City

"Tons of space. Awesome location. House looks well used, not super clean but usable. Parking was convenient."

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Stay near popular Eastern Shore attractions

A vibrant amusement park with a large red Ferris wheel, a yellow roller coaster, and various colorful rides.

Ocean City Boardwalk

9.0/10 (11,302 reviews)

This historic three-mile boardwalk has delighted visitors with ocean views and carnival charm since 1902. Savour local favourites like Thrasher's French Fries while exploring vintage amusement rides at Trimper's.

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A pier with people on it, a beach, and a roller coaster in the background.

Ocean City Beach

9.2/10 (10,973 reviews)

This classic 10-mile stretch of Atlantic shoreline pairs pristine sand with a vibrant, attraction-filled boardwalk. Enjoy free beach access year-round, with seasonal festivals adding extra charm to your coastal getaway.

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A wooden boardwalk by a body of water with binoculars and a bench.

Inlet Park

8.6/10 (1,457 reviews)

Gaze across the Atlantic towards Assateague Island from this peaceful coastal viewpoint. The park's wooden "Whispering Giant" sculpture honours Native American heritage while offering wildlife spotting.

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Roland E. Powell Convention Center

8.0/10 (2,358 reviews)

This modern bayfront venue hosts Ocean City's premier events, from trade shows to concerts. Enjoy panoramic water views while attending diverse exhibitions in its state-of-the-art facilities.

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A carousel, a large statue, and a building with a neon sign.

Jolly Roger Amusement Park

8.2/10 (3,806 reviews)

This dual-location amusement park features ocean-view rides at the Pier and thrilling water attractions at 30th Street. Enjoy illuminated attractions and panoramic Atlantic views from the Giant Wheel.

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A vibrant amusement park with a Ferris wheel, a prize factory, and various rides and attractions.

Jolly Roger at the Pier

8.4/10 (2,874 reviews)

This lively boardwalk amusement park dazzles with iconic rides like the Giant Wheel and Looping Star Roller Coaster. Evening visits offer magical views when colourful lights illuminate against the Atlantic sky.

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Salisbury University

8.4/10 (452 reviews)

Salisbury University's picturesque campus blends historic and modern architecture. Explore the Patricia R. Guerrieri Academic Commons for panoramic views and check the event calendar for cultural performances.

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Learn more about Eastern Shore

Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savour fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

See all hotels in Eastern Shore

Top Eastern Shore Hotel Reviews

Bonita Beach Hotel

10/10 Excellent

"It's a very good hotel for the price they have a heated pool but we spent most of our time on the beach which is a short walk from the hotel.nice rooms just very humid outside of the rooms. Staff was nice and helpful."

Princess Royale Oceanfront Resort

10/10 Excellent

"Clean rooms, clean hotel, delicious spa water in the lobby"

Quality Inn Oceanfront

8/10 Good

"bathroom tub and fixtures needs to be upgraded. Staff is both courtesy and helpful."

Castle in the Sand

8/10 Good

"I recently stayed in a Cottage. It was overall a good experience the Cottage was clean and bigger than I imagined. The pool was very clean and huge wasn’t busy at all during the stay. The breakfast buffet was decent but slightly pricy for what you get was $70 for 3 adults."

Grand Hotel Ocean City Oceanfront

10/10 Excellent

"This is the 2nd time I’ve stayed here and would do it again!"

Plim Plaza Hotel

8/10 Good

"The staff was great. The bathroom had some dirt in the corners, but otherwise was clean. In the windowsill there was evidence of mice. The fridge and TV worked great, and the beds were comfortable. The location is excellent, and the view from the window was nice."

Fenwick Inn

8/10 Good

"I had a nice stay at the fenwick inn, it was a great value, but the hotel is somewhat old and even with renovations it still shows its age"

Comfort Suites Ocean City West

8/10 Good

"The only thing was the tub looked so bad dirty stains"