Winchester-on-the-Severn Vacations
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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. Learn more about Winchester-on-the-Severn
Historic District
2 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.
Winchester-on-the-Severn Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AEDĀ 419 per night from Jul 30 to Jul 31
AEDĀ 419
AEDĀ 477 total
30 Jul - 31 Jul
includes taxes & fees
8.8/10 Excellent! (1,046 reviews)
"everything was perfect. Just the bathroom needs better cleaning overall it was great"
Reviewed on 21 July 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AEDĀ 419 per night from Jul 29 to Jul 30
AEDĀ 419
AEDĀ 603 total
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (1,896 reviews)
"My husband and I loved staying at the Inn. It was perfect!!! Everyone was kind and helpful. Our room was incredible!!"
Reviewed on 21 July 2026
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
The price is AEDĀ 291 per night from Jul 30 to Jul 31
AEDĀ 291
AEDĀ 332 total
30 Jul - 31 Jul
includes taxes & fees
8.2/10 Very Good! (4,700 reviews)
"The the elevator was not working and I was on the fourth floor, also the rooms were not clean and smell like smoke"
Reviewed on 21 July 2026
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.