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

4 Star Hotels in Eastern Shore, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore 4 Star Hotels

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for Eastern Shore 4-star hotels

Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
Exterior
Building design
Daily cooked-to-order breakfast for a fee

1. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
Taewook
€242
includes taxes & fees
3 Sept - 4 Sept
Hyatt Regency Chesapeake Bay
In-room safe, desk, laptop workspace, blackout curtains
Exterior
2 restaurants; breakfast, lunch and dinner served
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers

2. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
United States
Darryl
€196
includes taxes & fees
23 Sept - 24 Sept
DoubleTree by Hilton Ocean City Oceanfront
Exterior
Exterior
View from room
Exterior

3. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
United States
Paula
€216
includes taxes & fees
22 Sept - 23 Sept
Hilton Ocean City Oceanfront Suites
Front of property – evening/night
Garden
Ballroom
Dining

4. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United Kingdom
Jamie
€227
includes taxes & fees
31 Aug - 1 Sept
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
Smart TV
Indoor wedding
Luxury Suite, 1 Bedroom, Balcony | Balcony view

5. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
€415
includes taxes & fees
26 Aug - 27 Aug
The Oaks Waterfront
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

6. Walk to Beach: Newly Remodeled Condo in Ocean City

Walk to Beach: Newly Remodeled Condo in Ocean City
North Ocean City
Walk to Beach: Newly Remodeled Condo in Ocean City
Apartment (2 Bedrooms) | Front of property
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

7. Deck w/ Canal Access: Ocean City Townhome

Deck w/ Canal Access: Ocean City Townhome
North Ocean City
United States
Brock
Deck w/ Canal Access: Ocean City Townhome
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

8. Walk to Ocean City Boardwalk: Waterfront Condo

Walk to Ocean City Boardwalk: Waterfront Condo
Downtown Ocean City
Walk to Ocean City Boardwalk: Waterfront Condo
Apartment (1 Bedroom) | Interior
Apartment (1 Bedroom) | Interior
Apartment (1 Bedroom) | Interior
Apartment (1 Bedroom) | Interior

9. Waterfront + Pool! Ocean City Condo 1 Mi to Beach

Waterfront + Pool! Ocean City Condo 1 Mi to Beach
North Ocean City
Waterfront + Pool! Ocean City Condo 1 Mi to Beach
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Eastern Shore.
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
€401
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (397 reviews)
Inn at Perry Cabin
Still don't see what you're looking for?
See all properties in Eastern Shore.
You can also use these popular filters to refine your search.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Top Eastern Shore Hotel Reviews

Frequently asked questions

What are the best 4-star hotels in Eastern Shore?
You can find a variety of 4-star hotels in Eastern Shore, including in Ocean City. Hilton Ocean City Oceanfront Suites is a guest favourite here that comes with a jetted bathtub and designer toiletries. Another stay that's recommended by travellers is DoubleTree by Hilton Ocean City Oceanfront. A swimming pool and a deep soaking bathtub help make it their number one choice.
How much does it cost to stay in a 4-star hotel in Eastern Shore?
Expedia can help you quickly track down the ideal 4-star hotel for your holiday in Eastern Shore. Use our filter tool to fine-tune your search by things like budget, amenities and star rating and get access to awesome deals in a few clicks.
  • Search for the lowest price from €401
What's the difference between 5-star and 4-star hotels in Eastern Shore?
Offering a welcoming traveller experience and upmarket surroundings, 4-star hotels are a great option for your Eastern Shore holiday. These kinds of stays generally feature lots of handy amenities that make it a breeze to unpack and unwind — think complimentary bathrobes, gyms and restaurants. Or live the high life at a 5-star hotel designed to pamper with exclusive perks and amenities. Full-service health clubs, premium toiletries and fine dining are typically included at these deluxe properties.

Explore a world of travel with Expedia