Top 10 Hotels in Eastern Shore (from $80) 2026 - Competitive Prices

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 indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

A marina with multiple boats docked during sunset.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

1. Historic Inns of Annapolis

Historic District

ian

$148 nightly

$169 total

Oct 4 - Oct 5

Total with taxes and fees

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

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

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.

2. The Tidewater Inn

Easton

Miriam

$181 nightly

$199 total

Sep 30 - Oct 1

Total with taxes and fees

An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.

A spacious dining area with high ceilings, large windows, and modern chandeliers.

A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

A marina with boats docked, a sandy beach, and a clear blue sky.

3. Hyatt Regency Chesapeake Bay

Cambridge

Jon

$245 nightly

$278 total

Oct 6 - Oct 7

Total with taxes and fees

A two-story building with a covered entrance and an American flag.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

A hotel room with two beds, a chair, and a painting on the wall.

4. St Michaels Inn

St. Michaels

Lynn

$91 nightly

$100 total

Oct 6 - Oct 7

Total with taxes and fees

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

A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

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

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.

5. Best Western Plus Easton Inn & Suites

Easton

Raheem

$129 nightly

$142 total

Sep 27 - Sep 28

Total with taxes and fees

A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.

A group of people toasting at a round table in a room with large windows and artwork on the walls.

A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.

A bedroom with a sloped ceiling, a wooden bed, a desk with a lamp, and a dresser.

6. Hummingbird Inn

Easton

Ann

$341 nightly

$375 total

Sep 27 - Sep 28

Total with taxes and fees

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

7. Graduate by Hilton Annapolis

Annapolis

princess

$155 nightly

$177 total

Oct 26 - Oct 27

Total with taxes and fees

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

8. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

$135 nightly

$149 total

Oct 4 - Oct 5

Total with taxes and fees

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.

9. Holiday Inn Express Easton by IHG

Easton

Emily

$134 nightly

$147 total

Oct 25 - Oct 26

Total with taxes and fees

A room with a view of a wooden deck and a gazebo by the water.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

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

10. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

$570 nightly

$627 total

Oct 26 - Oct 27

Total with taxes and fees

A modern lobby with a seating area, a fireplace, and a bookshelf.

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

A restaurant with a yellow cushioned bench, wooden tables, and chairs.

11. Hilton Garden Inn Annapolis Downtown

Annapolis

Jeffrey

$130 nightly

$148 total

Oct 19 - Oct 20

Total with taxes and fees

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

A kitchen with a stone wall, a microwave, and various food items on the counter.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.

A residential area with a large building, a swimming pool, and well-maintained lawns.

12. Baymont by Wyndham Easton

Easton

Erik

$99 nightly

$109 total

Sep 27 - Sep 28

Total with taxes and fees

A modern hotel dining area with a long table, four chairs, and three pendant lights.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

13. Hampton Inn Easton

Easton

Rachel

$155 nightly

$171 total

Oct 1 - Oct 2

Total with taxes and fees

A two-story house with a porch, a front door, and a small garden area.

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

14. The Wildset

Downtown St. Michaels

Sarah

$262 nightly

$288 total

Oct 5 - Oct 6

Total with taxes and fees

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

A beach with clear water, sandy shore, and some vegetation.

A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.

A waterfront bar with outdoor seating, a view of the water, and American flags.

15. Sandaway Suites & Beach

Oxford

Amber

$333 nightly

$367 total

Sep 29 - Sep 30

Total with taxes and fees

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

16. The Westin Annapolis

Annapolis

Bobbi

$199 nightly

$227 total

Oct 25 - Oct 26

Total with taxes and fees

A balcony with a table set for two, overlooking a marina with boats.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

A waterfront area with boats docked, a clear sky, and buildings in the background.

17. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

$254 nightly

$290 total

Oct 12 - Oct 13

Total with taxes and fees

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

A white colonial-style house with a covered porch, brick steps, and outdoor seating.

A wooden console table with framed floral artwork, two lamps, and two ottomans.

A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

18. The Oaks Waterfront

Easton

Jeffrey

$489 nightly

$538 total

Sep 27 - Sep 28

Total with taxes and fees

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

A building with a sign reading "EcoLodge."

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

A hotel reception area with a check-in counter, a digital display, and a red carpet with the hotel's name.

19. Econo Lodge Easton Route 50

Easton

Brady

$81 nightly

$89 total

Oct 4 - Oct 5

Total with taxes and fees

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

20. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

$214 nightly

$238 total

Oct 19 - Oct 20

Total with taxes and fees

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Vacation 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 modern kitchen with a built-in refrigerator, a dining area with a table and chairs, and a large window with blinds.

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.

Shore Point Cottages

Berlin

"Easy accessible"

Aparthotel

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

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.

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

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:)"

Apartment

A wooden deck with white Adirondack chairs and a small round table.

A hotel room with two beds, a TV mounted on the wall, a window with blinds, and an air conditioning unit.

A two-story house with a front porch, a balcony on the second floor, and a small front yard.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink with a dish rack.

Safari Apartments

Downtown Ocean City

"Friendly staff. Easy check in/out. Clean place. Great area close to the boardwalk. Will definitely rent again."

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 kitchen with wooden cabinets, a stainless steel sink, a stove, a microwave, and a coffee maker.

Ocean Terrace Family Apartments

Downtown Ocean City

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

Apartment

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

A kitchen with white cabinets, a stove, a sink, and a dish rack.

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

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

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"

Cabin

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

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

A park with a wooden bridge over a pond, surrounded by trees and a bench.

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."

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

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

Saint Tropez

North Ocean City

"Great place to stay at definitely worth it"

Condo

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

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.

A sunset over a beach with waves gently lapping at the shore.

Americana Condos 10th street

Downtown Ocean City

"Wonderful views and so big!"

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

A living room with a green sofa, a wooden coffee table, a white fireplace, and a wicker chair.

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

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.

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

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

A hotel room with a large bed, a dresser, a TV, 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.

Bay Club Resort by Coolvacay

Midtown Ocean City

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

Condo

A living room with floral-patterned sofas, a wooden coffee table, and a TV mounted on the wall.

A spacious living room with a dining area, large windows, and a ceiling fan.

A coastal residential area with multi-story buildings, a clear sky, and a view of the ocean.

A hallway leading to a bedroom with a bed, a chair, and a lamp.

Americana Princess Suites and Condos

Downtown Ocean City

"This is a decent place to stay. Very walkable. Condo is a nice size! Plenty of room for 2 families of 3. Had a plumbing issue and the staff addressed it very quickly! Would stay here again. "

Condo

A bathroom with a large white vanity, a bathtub, and a window with floral curtains.

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

OCHG Townhouse 102 10

Downtown Ocean City

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

Condo

A covered patio with a table and chairs, a sliding glass door, and a white fence.

A pool area with a view of a two-story building, lounge chairs, and a bowl of fruit.

A compact kitchen with wooden cabinets, a refrigerator, microwave, stove, and dishwasher.

A living room with a sofa, a coffee table, a TV mounted on the wall, and a door leading to an outdoor area.

Monte Carlo Condos

Downtown Ocean City

"Unexpected pet fee on top of resort fees we did expect. Nice and close to boardwalk. Room was quiet, private, spacious."

Cottage

A two-story house with a covered porch, wooden posts, and a red and white trim.

A wooden dock leading to a restaurant named Bayside Inn.

A room with a wooden table, a hanging light fixture, and a view of the outdoors.

A spacious living room with a foosball table, a sofa, and a dining area with chairs and a table.

Pet-friendly Smith Island Cottage w/ Golf Cart!

Smith Island

"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."

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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. Savor local favorites 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 toward Assateague Island from this peaceful coastal viewpoint. The park's wooden "Whispering Giant" sculpture honors 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 colorful 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 savor 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

Plim Plaza Hotel

10/10 Excellent

"Accessibility to beach and main attractions on boardwalk"

Crystal Beach Hotel

8/10 Good

"Good time"

Dunes Suites Oceanfront

10/10 Excellent

"Clean and Direct oceanfront"

Fenwick Inn

10/10 Excellent

"This is one of the best hotels in the city. Good customer service and spacious rooms. We stayed for 3 days and enjoyed our stay at the hotel. They also have a beautuful rooftop restaurant with a city view. A good place for short or long term stay."

Carousel Resort Hotel & Condominiums

10/10 Excellent

"I love the beach view so nice to watch the water"

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good

"Very clean, bedding, floors, bath Excellent beach view. Would stay here again"

Francis Scott Key Family Resort

10/10 Excellent

"Great place for kids to have fun and enjoy a vacation. It was close to everything and the food onsite was good. The room was beautifully clean and comfortable. Would definitely stay again. Thank you."

Majestic Hotel & Apartments

8/10 Good

"The hotel had been renovated recently but the room I was in had not been updated. The bathroom had a very old sink and toilet and the towel holder was rusty. The bed was comfortable, the air conditioner worked, and there was a mini-fridge. The lobby area was clean and the staff was very friendly. There is an extra fee to pay for their parking lot and it's a little difficult to navigate the lot but as parking in the area is very limited, it's necessary to deal with."

More cheap stays in Eastern Shore

Plim Plaza Hotel

109 North Atlantic Ave. Ocean City MD

$76 nightly

$85 total

Oct 14 - Oct 15

Total with taxes and fees

Crystal Beach Hotel

2500 N. Baltimore Ave. Ocean City MD

$79 nightly

$88 total

Sep 28 - Sep 29

Total with taxes and fees

8.2/10 Very Good! (1,449 reviews)

Princess Bayside Beach Hotel

4801 Coastal Highway Ocean City MD

$79 nightly

$89 total

Oct 8 - Oct 9

Total with taxes and fees

Comfort Suites Ocean City West

12718 Ocean Gateway Ocean City MD

$79 nightly

$90 total

Oct 18 - Oct 19

Total with taxes and fees

8.4/10 Very Good! (1,006 reviews)

Quality Inn Ocean City Beachfront

2910 N Baltimore Ave Ocean City MD

$89 nightly

$100 total

Sep 28 - Sep 29

Total with taxes and fees

7.4/10 Good! (1,102 reviews)

Quality Inn Oceanfront

5400 Coastal Hwy Ocean City MD

$89 nightly

$100 total

Oct 4 - Oct 5

Total with taxes and fees

Hotels in Eastern Shore with star-rating

Find out more about Eastern Shore

Top reasons to visit Eastern Shore

Stunning Beaches: The Eastern Shore is renowned for its beautiful ocean beaches and scenic views of the Chesapeake Bay, perfect for sunbathing and water activities.
Charming Towns: Explore quaint towns like St. Michaels and Easton, rich in history and hospitality, offering unique shops and local cuisine.
Outdoor Adventures: Enjoy a variety of outdoor activities, from watersport rentals to hiking in urban parks and marinas.
Iconic Lighthouses: Discover the region's historic lighthouses, which add to the picturesque coastal landscape.
Diverse Accommodations: Choose from charming bed & breakfasts to modern hotels, catering to all travelers' needs.

Find great hotels near Eastern Shore

Eastern Shore, Maryland, offers a diverse selection of accommodations, from charming bed & breakfasts to modern hotels. Whether you're seeking pet-friendly options, a welcoming space for LGBTQIA travelers, or facilities suited for business travel, you'll find a variety of choices to enhance your stay. With stunning waterfront properties and popular hotels, this picturesque region is perfect for a relaxing getaway or an adventurous vacation.

Best Western Plus Easton Inn & Suites: This modern hotel combines comfort with convenience, boasting a stellar guest rating of 9.2. Located a mere 0.1 miles from Eastern Shore, it’s an ideal choice for business travelers seeking a productive stay. The hotel features spacious rooms equipped with complimentary Wi-Fi, a well-appointed fitness center, and a refreshing indoor pool. Guests can enjoy a complimentary hot breakfast to kickstart their day. The property’s close proximity to local businesses and attractions makes it a smart option for those looking to balance work and leisure during their visit.
St Michaels Inn: A perfect blend of adventure and comfort, St Michaels Inn earns a commendable guest rating of 8.2. Situated 8 miles from Eastern Shore, this hotel caters to those who crave outdoor excitement. With activities like hiking, biking, and fishing available nearby, it’s ideal for adventure seekers. The inn offers cozy accommodations and a welcoming atmosphere, making it a great base for exploring the local scenery. Guests appreciate the friendly service and the range of recreational options, ensuring an exhilarating stay filled with memorable experiences.
Quality Inn: This pet-friendly hotel is perfect for travelers looking to bring their furry companions along. Located 0.2 miles from Eastern Shore, Quality Inn offers a comfortable stay with a focus on convenience and accessibility. The property allows pets, with specific policies that cater to dog owners, making it an ideal choice for those who don’t want to leave their pets behind. Guests can enjoy a complimentary breakfast and access to a business center, making it suitable for both leisure and business travelers. The welcoming environment and practical amenities ensure a pleasant stay for all guests.

Where to stay near Eastern Shore

Eastern Shore, Maryland, offers a delightful vacation experience with its beautiful ocean beaches and scenic views of the Chesapeake Bay. Visitors can enjoy family-friendly activities in charming towns like St. Michaels and Easton, rich in history and hospitality. Whether you’re seeking outdoor adventures or relaxing excursions, the Eastern Shore is the perfect destination for travelers looking to explore a blend of natural beauty and welcoming communities.

Easton: Nestled a mile away from the Eastern Shore, Easton is a charming city that offers a delightful blend of outdoor experiences, stunning scenery, and local culture. While traveler arrivals may fluctuate throughout the year, peak seasons from June to July and September draw visitors eager to enjoy the picturesque boardwalk, vibrant shopping centers, and recreational areas. Easton is known for its proximity to beautiful beaches and the serene bay, making it an ideal spot for families seeking a relaxing getaway. Whether you’re strolling along the waterfront or exploring local boutiques, Easton promises a memorable vacation experience.
St. Michaels: Located 9 miles from the Eastern Shore, St. Michaels is a quaint city that embodies the charm of the Chesapeake Bay region. With moderately seasonal travel patterns, the peak months of April and June to July attract those looking for outdoor adventures and breathtaking scenery. Visitors can enjoy the inviting boardwalk and various recreational areas, all while soaking in the coastal atmosphere. The nearby beaches and family-friendly attractions make St. Michaels a perfect destination for families and nature lovers alike. Experience the local seafood cuisine and explore the unique shops that define this picturesque town.
Tanyard: Situated 5 miles away from Eastern Shore, Tanyard is a quaint village that offers a unique experience for travelers, particularly those with business interests. While visitor numbers peak during the summer months from June to August, Tanyard’s charm lies in its serene atmosphere and close-knit community vibe. The village is ideal for business-themed travelers looking for a peaceful retreat with easy access to local amenities. Despite its smaller size, Tanyard provides a perfect backdrop for a tranquil getaway combined with potential networking opportunities.

Things to do in Eastern Shore

The Eastern Shore of Maryland offers a perfect blend of outdoor adventures and scenic beauty. Visitors can enjoy a variety of activities including watersport rentals, exploring charming cities, and leisurely strolls along the boardwalk. Recreational areas provide ample opportunities for relaxation and fun, while shopping experiences and safaris add a unique twist to your vacation. Whether you're seeking beach time or vibrant local culture, the Eastern Shore has something for everyone.

Shopping

Discover the charming shops at The Eastern Shore Shopping Center, offering a mix of local boutiques and popular retailers. Don't miss the unique finds at St. Michaels Farmers Market, where you can pick up handcrafted gifts and delicious local produce, making for perfect souvenirs.

Recreation

At the Hyatt Regency Chesapeake Bay, indulge in rejuvenating spa services and serene waterfront views. Visit the Tranquility Wellness Spa for holistic treatments and yoga sessions that harmonize mind and body, fostering relaxation and renewal amidst the beauty of the Eastern Shore.

Adventure

Explore the stunning landscapes of Assateague Island National Seashore, where you can kayak alongside wild ponies and enjoy breathtaking sunsets. For a thrill, try parasailing in Ocean City, offering sweeping views of the coastline and the exhilarating feeling of soaring above the water.

Nightlife

The nightlife in Eastern Shore, Maryland, is vibrant and diverse. Enjoy live music at the Avalon Theatre, or unwind at local bars like the Red Eye's Dock Bar, where you can savor cocktails and waterfront views. For a unique experience, visit the historic downtown area for charming pubs and late-night eateries.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Eastern Shore

The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Eastern Shore are January to February and November, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Eastern Shore is Tuesday. The most expensive day to stay around Eastern Shore is Saturday.
Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, preferred location, and ideal type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, arrange the price filter from lowest to highest.
Consider bundling your trip: You can save money by combining your hotel stay on the Eastern Shore with your flights and activities through an Expedia package deal.

Find the best attractions near Eastern Shore

Eastern Shore, Maryland, offers a perfect getaway for outdoor enthusiasts and families, boasting stunning beaches and picturesque scenery. Visitors can explore a variety of attractions, including urban parks, marinas, and iconic lighthouses. Whether you're seeking adventure or cultural experiences, Eastern Shore has something for everyone to enjoy in its beautiful natural surroundings.

Chesapeake Bay Maritime Museum: Located 9 miles from Eastern Shore, this maritime museum offers a deep dive into the rich maritime heritage of the Chesapeake Bay. Explore interactive exhibits, historic vessels, and beautiful waterfront views, all while soaking in the area's culture and history.
The Third Haven Friends Meeting House: Just 2 miles away, this historic house is a serene place of worship with stunning architecture and tranquil gardens. Visitors can learn about the Quaker faith and its historical significance in the region, all wrapped in peaceful surroundings.
Academy of the Arts: Only 1 mile from Eastern Shore, this art museum showcases a diverse range of artistic expressions, including visual arts and performances. Engage with local talent and enjoy rotating exhibitions that highlight the cultural vibrancy of the area.

Best time to go to Eastern Shore

The best time to visit Eastern Shore is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Average	Average
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Average
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	78.3°F (25.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	77.7°F (25.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	70.9°F (21.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	50.9°F (10.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	39.9°F (4.4°C)	Light Rain	Mostly Sunny	Average	Average

The nearest major airports for your trip to Eastern Shore

Traveling to the Eastern Shore of Maryland is convenient with several major airports nearby. Philadelphia International Airport (PHL), located 87 miles away, offers luxury accommodations like the W Philadelphia and The Rittenhouse, both only 6 miles from the airport. Ronald Reagan Washington National Airport (DCA), 53 miles from Eastern Shore, features upscale hotels such as the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both within 2 miles. Washington Dulles International Airport (IAD) is 76 miles away, with excellent options like The Westin Washington Dulles Airport and Hyatt Regency Dulles, just 1 mile from the terminal. Each airport provides accessible transportation to these hotels.

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Our top choices for Eastern Shore hotels

1. Historic Inns of Annapolis

2. The Tidewater Inn

3. Hyatt Regency Chesapeake Bay

4. St Michaels Inn

5. Best Western Plus Easton Inn & Suites

6. Hummingbird Inn

7. Graduate by Hilton Annapolis

8. Fairfield Inn & Suites by Marriott Easton

9. Holiday Inn Express Easton by IHG

10. Inn at Perry Cabin

11. Hilton Garden Inn Annapolis Downtown

12. Baymont by Wyndham Easton

13. Hampton Inn Easton

14. The Wildset

15. Sandaway Suites & Beach

16. The Westin Annapolis

17. Annapolis Waterfront Hotel, Autograph Collection

18. The Oaks Waterfront

19. Econo Lodge Easton Route 50

20. The Inn at Chesapeake Bay Beach Club

Vacation Rentals in Eastern Shore

Shore Point Cottages

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Safari Apartments

Ocean Terrace Family Apartments

Cambridge Apt in Walkable Neighborhood

Strawberry Crossroads

Saint Tropez

Americana Condos 10th street

OCHG VIRGINIA LEE

OCHG Bel Harbour Unit 1

Bay Club Resort by Coolvacay

Americana Princess Suites and Condos

OCHG Townhouse 102 10

Monte Carlo Condos

Pet-friendly Smith Island Cottage w/ Golf Cart!

Stay near popular Eastern Shore attractions

Ocean City Boardwalk

Ocean City Beach

Inlet Park

Roland E. Powell Convention Center

Jolly Roger Amusement Park

Jolly Roger at the Pier

Salisbury University

Learn more about Eastern Shore

Top Eastern Shore Hotel Reviews

Plim Plaza Hotel

Crystal Beach Hotel

Dunes Suites Oceanfront

Fenwick Inn

Carousel Resort Hotel & Condominiums

Days Inn by Wyndham Ocean City Oceanfront

Francis Scott Key Family Resort

Majestic Hotel & Apartments

More cheap stays in Eastern Shore

Plim Plaza Hotel

Crystal Beach Hotel

Princess Bayside Beach Hotel

Comfort Suites Ocean City West

Quality Inn Ocean City Beachfront

Quality Inn Oceanfront

Hotels in Eastern Shore with star-rating

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Where to stay near Eastern Shore

Things to do in Eastern Shore

Booking tips and Expedia advantages for Eastern Shore

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Best time to go to Eastern Shore