A large brick house with a green roof, surrounded by lush gardens and trees.

Find Oceanfront Hotels in Sherwood, MD from CA $289

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Check availability on Sherwood Oceanfront Hotels

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Sherwood hotels with an ocean view

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A spacious indoor dining area with large windows, tables, and chairs.
A waterfront property with a dock, a sailboat, and a building with a red roof.
A large building with a swimming pool, dock, and green surroundings.

1. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
CA $263
CA $289 total
includes taxes & fees
Oct 19 - Oct 20
The Tilghman Island Inn
A waterfront property with a covered patio, a dock, and a boat.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.
A waterfront hotel with a covered dock and a large building with multiple balconies.

2. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
United States
Gary
CA $281
CA $380 total
includes taxes & fees
Oct 17 - Oct 18
Wylder Tilghman Island
A balcony with a table set for two, overlooking a marina with boats.
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.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

3. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
CA $317
CA $361 total
includes taxes & fees
Nov 1 - Nov 2
Annapolis Waterfront Hotel, Autograph Collection
View all properties

Top Sherwood Hotel Reviews

St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 7 hours ago
St Michaels Inn
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

10/10 Excellent
"The staff was extremely helpful and the view was amazing. I will definitely be returning."
MAURICE 2-night trip
Posted 2 days ago
Knapps Narrows Marina & Inn

Frequently asked questions

What is Sherwood like for a seaside holiday?
Make your Sherwood vacation special by staying somewhere with a sea view. Choose a place next to the sailing venue for some quality time by the water. When you want a break from the beach, check out the waterfront and restaurants.
What are the highlights to see in Sherwood?
After arriving and settling in at your accommodation of choice, you might want to venture out and explore. Beach lovers can head straight to Breezy Point Beach or Bay Ridge Beach for some quality time by the water. Discover a variety of local attractions, which include Knapp's Narrows Marina & Inn and Goat Island. You can also pay a visit to St. Michaels Winery or Saint Michaels Town Hall for more to see and do.
Why should I choose an oceanview hotel for my Sherwood vacation?
Spoil yourself with an oceanview room and enjoy amazing beach views during your vacation to Sherwood. Expedia makes it simple to select the ideal hotel when you use our ocean view filter in the search results to narrow down your search.

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