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

Sep 1 - Sep 2

"Great stay beautiful view"

CA $200 total

includes taxes & fees

Aug 24 - Aug 25

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

"I like the location and how easy it is to get to our room."

CA $166 total

includes taxes & fees

Aug 20 - Aug 21

"Great place to stay. "

CA $243 total

includes taxes & fees

Aug 21 - Aug 22

"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 18 - Aug 19

"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

"Great location and amenities"

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 $137 total

includes taxes & fees

Aug 17 - Aug 18

"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "

CA $308 total

includes taxes & fees

Aug 18 - Aug 19

"Great stay"

CA $207 total

includes taxes & fees

Aug 25 - Aug 26

"Beautiful hotel in a great location!"

CA $252 total

includes taxes & fees

Sep 2 - Sep 3

"Really nice place to stay and enjoy Annapolis "

CA $145 total

includes taxes & fees

Aug 27 - Aug 28

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

CA $250 total

includes taxes & fees

Aug 24 - Aug 25

"complimentry breakfast is good ,friendly staff,clean and quite "

CA $199 total

includes taxes & fees

Aug 24 - Aug 25

"The hotel staff and accommodations were exceptional."

CA $212 total

includes taxes & fees

Aug 18 - Aug 19

"The staff specifically Victoria was impeccable! "

CA $281 total

includes taxes & fees

Sep 1 - Sep 2

"Bed was great"

CA $152 total

includes taxes & fees

Aug 18 - Aug 19

"Good location"

CA $170 total

includes taxes & fees

Aug 24 - Aug 25

"Great stay"

CA $147 total

includes taxes & fees

Aug 18 - Aug 19

"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 31 - Sep 1

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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