Find hotels in Winchester-on-the-Severn, Annapolis from ₩75,128

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 12 - Aug 13
Tomorrow
Aug 13 - Aug 14
This weekend
Aug 15 - Aug 17
Next weekend
Aug 22 - Aug 24

Filter by

Guest rating
Guest rating
Star rating

Discover 1,263 Winchester-on-the-Severn hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (604)
"Great place to stay. "
The price is ₩221,252
₩245,589 total
includes taxes & fees
Aug 21 - Aug 22
Hyatt Place Kent Narrows & Marina
Holiday Inn Express Baltimore At The Stadiums by IHG
Free daily buffet breakfast

Holiday Inn Express Baltimore At The Stadiums by IHG

2.5 star property
8.4 out of 10, Very Good, (278)
"Fantastic stay!!!"
The price is ₩132,194
₩155,335 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Baltimore At The Stadiums by IHG
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (982)
"Friendly staff, nice environment"
The price is ₩211,915
₩235,225 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Kent Island Marina
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1006)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is ₩221,252
₩252,228 total
includes taxes & fees
Aug 24 - Aug 25
The Westin Annapolis
Hilton Garden Inn Annapolis
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very Good, (1006)
"Such friendly staff"
The price is ₩132,473
₩151,019 total
includes taxes & fees
Aug 18 - Aug 19
Hilton Garden Inn Annapolis
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1006)
"Great place and great staff "
The price is ₩146,110
₩166,566 total
includes taxes & fees
Aug 19 - Aug 20
Courtyard by Marriott Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (408)
"Great location and amenities"
The price is ₩285,262
₩352,041 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is ₩236,697
₩313,947 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort
Courtyard by Marriott Baltimore Downtown/McHenry Row
Property amenity

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
9.0 out of 10, Wonderful, (641)
"Convenient for cruise port"
The price is ₩174,079
₩204,543 total
includes taxes & fees
Aug 17 - Aug 18
Courtyard by Marriott Baltimore Downtown/McHenry Row
Hampton Inn & Suites Annapolis
Premium bedding, pillowtop beds, in-room safe, individually furnished

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very Good, (1008)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is ₩139,736
₩159,299 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Annapolis
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"Nice place nice the people work over there"
The price is ₩148,600
₩174,605 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus Hotel & Conference Center
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1009)
"I like the location and how easy it is to get to our room."
The price is ₩151,370
₩168,021 total
includes taxes & fees
Aug 19 - Aug 20
Best Western Kent Narrows Inn
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout drapes

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1008)
"Great visit "
The price is ₩134,838
₩153,715 total
includes taxes & fees
Aug 19 - Aug 20
Country Inn & Suites by Radisson, Annapolis, MD
Comfort Suites Columbia Gateway
Front of property

Comfort Suites Columbia Gateway

2.5 star property
8.2 out of 10, Very Good, (1001)
"The breakfast options was very good and acceptable "
The price is ₩123,984
₩140,101 total
includes taxes & fees
Aug 14 - Aug 15
Comfort Suites Columbia Gateway
Holiday Inn Express & Suites Annapolis by IHG
Free daily buffet breakfast

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1001)
"Bed was great"
The price is ₩134,977
₩153,874 total
includes taxes & fees
Aug 18 - Aug 19
Holiday Inn Express & Suites Annapolis by IHG
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1832)
"Great stay"
The price is ₩141,818
₩209,262 total
includes taxes & fees
Aug 19 - Aug 20
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1004)
"The Double Tree was a great place to stay! Great location amd the staff are very pleasant and helpful! "
The price is ₩139,597
₩159,140 total
includes taxes & fees
Aug 20 - Aug 21
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG
Pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1007)
"Nice spot in a convenient but quiet area. "
The price is ₩155,850
₩177,669 total
includes taxes & fees
Aug 28 - Aug 29
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis
1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (853)
"Great room for a great price... Very friendly staff, too."
The price is ₩129,690
₩147,846 total
includes taxes & fees
Aug 19 - Aug 20
Sonesta ES Suites Annapolis
SpringHill Suites by Marriott Annapolis
Free daily self-serve breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great place"
The price is ₩146,666
₩167,199 total
includes taxes & fees
Aug 18 - Aug 19
SpringHill Suites by Marriott Annapolis
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.

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 which includes street scenes and a city as well as a small group of people
Historic District map

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.

Eastport map

Eastport

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

Murray Hill map

Murray Hill

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

Cape Saint Claire map

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.

Maryland Quiet Waters Park featuring a garden and a house
Hillsmere map

Hillsmere

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

Top Winchester-on-the-Severn Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Charming area and loved to hotel decor!"
Elizabeth 3-night trip
Posted 11 hours ago
Historic Inns of Annapolis

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.