Find Oceanfront Hotels in Sherwood, MD

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Sherwood Oceanfront Hotels

Tonight
Sep 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

Top Sherwood Oceanfront Hotels

Our top choices for Sherwood hotels with an ocean view

Wylder Tilghman Island
Widows Walk Suite | Terrace/patio

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (67)
"Good service and good options to enjoy the stays. "
The price is CA $233
CA $317 total
includes taxes & fees
Sep 18 - Sep 19
Wylder Tilghman Island
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (105)
"Great staff and food!"
The price is CA $296
CA $325 total
includes taxes & fees
Sep 14 - Sep 15
The Tilghman Island Inn
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (859)
"Easy check in, clean and close to everything "
The price is CA $326
CA $372 total
includes taxes & fees
Sep 28 - Sep 29
Annapolis Waterfront Hotel, Autograph Collection
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Outdoor dining

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

The price is CA $2,968
CA $4,178 total
includes taxes & fees
Sep 6 - Sep 7
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
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.

Find out more about Sherwood

Find out more about Sherwood

Popular beach getaways

Most booked beach stays in Sherwood in 2025

Kid-friendly beach stays in Sherwood
Kid-friendly beach stays
Kid-friendly beach stays
Hotels with pools in Sherwood
Hotels with pools
Hotels with pools

Top Sherwood Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia