10 Best Hotels in Winchester-on-the-Severn, Annapolis for 2025

Winchester-on-the-Severn hotels and places to stay

"Friendly staff, nice environment"

CA $233 total

includes taxes & fees

Aug 24 - Aug 25

"Great stay beautiful view"

CA $206 total

includes taxes & fees

Aug 17 - Aug 18

In-room safe, individually decorated, individually furnished, desk

"A remarkable weekend getaway "

CA $166 total

includes taxes & fees

Aug 13 - Aug 14

"Great place to stay. "

CA $242 total

includes taxes & fees

Aug 26 - Aug 27

"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "

CA $237 total

includes taxes & fees

Aug 10 - Aug 11

"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."

CA $311 total

includes taxes & fees

Sep 1 - Sep 2

"Staff was very polite and friendly. "

CA $348 total

includes taxes & fees

Aug 24 - Aug 25

"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."

CA $140 total

includes taxes & fees

Aug 7 - Aug 8

"We’ve been here a few times and continue to to love the location, staff and comfortable beds. "

CA $207 total

includes taxes & fees

Aug 17 - Aug 18

"Charming spot close to everything with excellent amenities and service. "

CA $243 total

includes taxes & fees

Aug 17 - Aug 18

"Really nice place to stay and enjoy Annapolis "

CA $159 total

includes taxes & fees

Sep 1 - Sep 2

"The Hotel was very clean and convenient to everything that we wanted to do!!!!"

CA $250 total

includes taxes & fees

Aug 13 - Aug 14

"The breakfast options were amazing."

CA $212 total

includes taxes & fees

Aug 24 - Aug 25

"The hotel staff and accommodations were exceptional."

CA $253 total

includes taxes & fees

Aug 11 - Aug 12

"The staff specifically Victoria was impeccable! "

CA $281 total

includes taxes & fees

Sep 1 - Sep 2

"Bed was very comfortable "

CA $146 total

includes taxes & fees

Aug 13 - Aug 14

"Very clean and friendly staff. Best mattress and pillows have had in hotel."

CA $192 total

includes taxes & fees

Aug 10 - Aug 11

"Great stay"

CA $154 total

includes taxes & fees

Aug 11 - Aug 12

"The Double Tree was a great place to stay! Great location amd the staff are very pleasant and helpful! "

CA $151 total

includes taxes & fees

Aug 10 - Aug 11

"It was very nice I will go there again"

CA $131 total

includes taxes & fees

Aug 10 - Aug 11

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Where to stay in Winchester-on-the-Severn

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

Annapolis showing street scenes and a city as well as a small group of people

Historic District

1 out of top 10 points of interest in this area

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.

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Eastport

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

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Murray Hill

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

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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.

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