Search Hotels in Winchester-on-the-Severn, Annapolis

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

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

Exterior
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
3.0 star property
25.4 km from Winchester-on-the-Severn
8.2 out of 10, Very good, (4347)
"Great stay!"
United States
Alissa
The price is 1.768.127 ₫
2.015.665 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
23.6 km from Winchester-on-the-Severn
9.2 out of 10, Wonderful, (935)
"It was very comfortable and clean"
United States
Maria
The price is 2.290.797 ₫
2.542.785 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
5 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1015)
"Great place!"
United States
Tawnya
The price is 1.964.819 ₫
2.239.894 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District, 4.3 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1904)
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
4.3 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1008)
"Great value for stay with breakfast included "
United States
Aisling
The price is 2.300.712 ₫
2.622.810 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Annapolis Downtown
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
5.4 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1000)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is 2.506.711 ₫
2.857.651 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
4.2 km from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (1004)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is 3.585.265 ₫
4.087.202 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Graduate by Hilton Annapolis
Hypo-allergenic bedding, down duvets, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
6.1 km from Winchester-on-the-Severn
8.2 out of 10, Very good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is 2.007.212 ₫
2.288.222 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Hilton Garden Inn Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
4.5 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1005)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is 2.764.755 ₫
3.151.821 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Crowne Plaza Annapolis by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
23.3 km from Winchester-on-the-Severn
9.6 out of 10, Exceptional, (675)
"Great view, good ambiance all around"
United States
Dianne
The price is 2.896.410 ₫
3.215.015 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Place Kent Narrows & Marina
Free daily continental breakfast
Wingate by Wyndham Baltimore BWI Airport

Wingate by Wyndham Baltimore BWI Airport

Wingate by Wyndham Baltimore BWI Airport
2.5 star property
25.5 km from Winchester-on-the-Severn
8.0 out of 10, Very good, (1210)
"I like the fact that it was very quiet the staff was very accommodating and the bed was very comfortable"
United States
Joan Annette
The price is 1.769.443 ₫
2.017.165 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Wingate by Wyndham Baltimore BWI Airport
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
4.7 km from Winchester-on-the-Severn
8.2 out of 10, Very good, (1000)
"Clean room and friendly staff! "
United States
Silvia
The price is 2.106.480 ₫
2.401.387 ₫ total
includes taxes & fees
10 Jan - 11 Jan 2026
Holiday Inn Express & Suites Annapolis by IHG
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
6 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1000)
"Wonderful stay. "
United States
Angela
The price is 2.211.804 ₫
2.521.456 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Annapolis
Indoor pool
The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve
3.5 star property
25.4 km from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (1570)
"Great ambiance and the grillfire restaurant is always a vibe! "
United States
Lateshia
The price is 3.334.821 ₫
3.801.696 ₫ total
includes taxes & fees
19 Dec - 20 Dec
The Hotel at Arundel Preserve
Free daily self-service breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
6 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1000)
"Great location and friendly staff. "
United States
Shana
The price is 2.663.381 ₫
3.036.255 ₫ total
includes taxes & fees
24 Dec - 25 Dec
SpringHill Suites by Marriott Annapolis
Courtyard
Hilton Baltimore BWI Airport

Hilton Baltimore BWI Airport

Hilton Baltimore BWI Airport
3.5 star property
25 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1001)
"Nice hotel "
United States
Quinntin
The price is 2.444.043 ₫
2.786.210 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Hilton Baltimore BWI Airport
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
5.7 km from Winchester-on-the-Severn
8.2 out of 10, Very good, (1002)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is 2.353.465 ₫
2.682.950 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn & Suites Annapolis
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
23.5 km from Winchester-on-the-Severn
8.0 out of 10, Very good, (1001)
"Nice place "
United States
Tucker T
The price is 2.196.532 ₫
2.438.151 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Best Western Kent Narrows Inn
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
4.3 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is 4.054.974 ₫
4.622.671 ₫ total
includes taxes & fees
19 Dec - 20 Dec
The Westin Annapolis
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
6 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (964)
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is 2.422.452 ₫
2.761.595 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Sonesta ES Suites 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.
View all properties

Where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas for the activities you enjoy most.
Annapolis featuring a city and street scenes as well as a small group of people

Historic District

While visiting Historic District, you might make a stop by sights like Thurgood Marshall Memorial and Maryland State House.

Eastport

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

Murray Hill

If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.

Cape Saint Claire

While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.

Maryland Quiet Waters Park showing a garden and a house

Hillsmere

While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.

Top Winchester-on-the-Severn Hotel Reviews

Frequently asked questions

What's it like in Winchester-on-the-Severn?
Travellers will be sure to enjoy their time in Annapolis's Winchester-on-the-Severn neighbourhood.
If I need to cancel my hotel reservation in Winchester-on-the-Severn, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of booking. Put your dates in and click on "Search", then filter by "fully refundable" to get the best deals in Winchester-on-the-Severn.
What is there to do in this Annapolis neighbourhood?
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.