Find hotels in Winchester-on-the-Severn, Annapolis

Where to?

Dates

June 2026

July 2026

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

Where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas and neighborhoods for the activities you enjoy most.

Aerial Panoramic View Annapolis Maryland State House Capital City

Historic District

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

See properties

Aerial view of colorful sailboat moorings and docks on Spa Creek, in historic downtown Annapolis Maryland on a fall day

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

See properties

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

See properties

Chesapeake Bay Bridge with blue and orange sunset

Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

See properties

Cape Saint Claire

Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.

See properties

Top Winchester-on-the-Severn Hotel Reviews

Best Western Plus Hotel & Conference Center

4/10 Poor

"Room was clean and nice. Breakfast was a typical hotel free breakfast, just ok. They have a bar but it closes early. So we couldn't use it when we got back to the hotel at 8:45 PM on a Friday night. You would have thought it would be open later on the weekend. Also this hotel has a conference center and banquet hall attached to it. The music was so loud and played all night till 5:00 AM we were not able to sleep at all. I contacted the front desk by text and it was ignored. 2 days later they sent me a text saying it should stop soon. If you stay here make sure you stay on the opposite side from the banquet center, or you too won't be able to sleep. We will never be staying here again. And we travel to this area every few months."

Wingate by Wyndham Baltimore BWI Airport

6/10 Okay

"There's nothing special about this property for the price we paid but due to our circumstances we needed a place to sleep for one night. Would we stay again? Not sure, at least not in that room. The room my husband and I was given was just ok, the bathroom not so much. Had to close the door because the toilet was running really loud and it didn't flush good. And the toilet paper holder needs to be updated, you might slice a finger. The tub needs to be reglazed due to the brown water stain. Shower curtains were ripped near the top and it kept sliding to the middle of the shower rod, not sure if that was due to the curved rod or not but the shower curtain wouldn't stay closed while showering. The area around the tub definitely needs a good caulking from their engineering dept. Check the wall behind the door too, it needs to be redone. The cabinet that holds the mini-fridge and microwave had what looks like saw dust (tan flakes) at the bottom that needed to be wiped out but the fridge and microwave were both clean enough to use. Ice machine displayed a sign that it wasn't working and it didn't tell you which floor to get ice, who wants to hunt for ice at 1am? I don't! Again not sure if we would return, this property needs some updating, which is why it was just okay for us and the reason we gave 3 stars."

Sonesta ES Suites Baltimore BWI Airport

4/10 Poor

"From the reviews I read and the pictures shown, I expected something completely different. The pool was not open as advertised and was filled with moldy green water. The washing machine was broken. There was vomit in the hallway, and the parking was not free as advertised as well. Breakfast was alright but on our last morning both my son and I got sick after eating the eggs. I am not writing this because I am angry or upset, I simply want to let people know what they’re getting instead of expecting something and being let down like I was."

Frequently asked questions

What's it like in Winchester-on-the-Severn?

Travelers will be sure to enjoy their time in Annapolis's Winchester-on-the-Severn neighborhood.

If I need to cancel my hotel reservation in Winchester-on-the-Severn, will I receive a refund?

Yes! Most hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Add dates, click "Search", then you can use the "fully refundable" filter to view the best deals in Winchester-on-the-Severn.

Where can I learn more about changing or cancelling my trip to Winchester-on-the-Severn?

To access more information about picking new dates or cancelling your trip to Winchester-on-the-Severn, click here.

What is there to do in this Annapolis neighborhood?

A few places to visit in the area around Winchester-on-the-Severn include Maryland World War II Memorial, Jonas Green State Park, and Helen Avalynne Tawes Garden. When you're sightseeing in Annapolis, Navy-Marine Corps Memorial Stadium and Severna Park Golf Center are also worth a stop.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Winchester-on-the-Severn on Expedia.com

Find hotels in Winchester-on-the-Severn, Annapolis

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for Winchester-on-the-Severn hotels

Holiday Inn Express Baltimore at the Stadiums by IHG

Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Kent Island Resort

Microtel Inn & Suites by Wyndham Gambrills

Motel 6 Laurel, DC - Washington Northeast

Wingate by Wyndham Baltimore BWI Airport

Candlewood Suites Annapolis by IHG

Americas Best Value Inn Laurel

Hilton Garden Inn Annapolis

Holiday Inn Express Baltimore - BWI Airport NE by IHG

Red Crown Inn

Anchored Inn at Hidden Harbour Marina

Best Western Annapolis

Historic Inns of Annapolis

Motel 6 Linthicum Heights, MD - BWI Airport

Hyatt Place Kent Narrows & Marina

Annapolis Waterfront Hotel, Autograph Collection

DoubleTree by Hilton Hotel Annapolis

Hilton Baltimore BWI Airport

Where to stay in Winchester-on-the-Severn

Historic District

Eastport

Murray Hill

Hillsmere

Cape Saint Claire

Top Winchester-on-the-Severn Hotel Reviews

Best Western Plus Hotel & Conference Center

Frequently asked questions

Explore a world of travel with Expedia