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
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Winchester-on-the-Severn, Annapolis

Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
United States
Michael
The price is ₹9,765
₹10,839 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (640)
"Nice location and restaurants galore in area. "
United States
David
The price is ₹13,108
₹14,550 total
includes taxes & fees
26 Oct - 27 Oct
Hyatt Place Kent Narrows & Marina
Free daily buffet breakfast
Holiday Inn Express Baltimore At The Stadiums by IHG
Holiday Inn Express Baltimore At The Stadiums by IHG
2.5 star property
8.6 out of 10, Excellent, (350)
"Great Place Places to Stay "
United States
Bhavesh R
The price is ₹8,709
₹10,234 total
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn Express Baltimore At The Stadiums by IHG
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
9.0 out of 10, Wonderful, (1006)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is ₹12,913
₹14,333 total
includes taxes & fees
26 Oct - 27 Oct
Hilton Garden Inn Kent Island Marina
Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
United States
Eric
The price is ₹16,627
₹21,760 total
includes taxes & fees
21 Oct - 22 Oct
Kent Island Resort
View from property
The Westin Annapolis
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1006)
"Would stay there again very soon "
United States
Robert
The price is ₹15,747
₹17,952 total
includes taxes & fees
26 Oct - 27 Oct
The Westin Annapolis
Front of property
Comfort Suites Columbia Gateway
Comfort Suites Columbia Gateway
2.5 star property
8.2 out of 10, Very good, (1002)
"Staff at this place were very nice "
United States
Sylvia
The price is ₹7,471
₹8,442 total
includes taxes & fees
16 Nov - 17 Nov
Comfort Suites Columbia Gateway
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very good, (1000)
"Clean room and good location to biking trail."
United States
Cynthia
The price is ₹8,095
₹8,986 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Kent Narrows Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn
Quality Inn
2.5 star property
7.8 out of 10, Good, (842)
"Great place and great staff"
United States
Rhonda
The price is ₹8,458
₹9,388 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn
Property amenity
Courtyard by Marriott Baltimore Downtown/McHenry Row
Courtyard by Marriott Baltimore Downtown/McHenry Row
3.0 star property
9.0 out of 10, Wonderful, (675)
"Great location "
United States
Kimberley
The price is ₹11,797
₹13,862 total
includes taxes & fees
2 Nov - 3 Nov
Courtyard by Marriott Baltimore Downtown/McHenry Row
Indoor pool
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 star property
8.8 out of 10, Excellent, (1004)
"Good location"
United States
William Charles Reinhart
The price is ₹8,797
₹10,029 total
includes taxes & fees
2 Nov - 3 Nov
Crowne Plaza Annapolis by IHG
Front of property
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour Marina
2.5 star property
9.4 out of 10, Exceptional, (463)
"Property was very nice. They only downside was a limited breakfast."
United States
Elisha
The price is ₹15,756
₹17,962 total
includes taxes & fees
21 Oct - 22 Oct
Anchored Inn at Hidden Harbour Marina
Lobby
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center
2.5 star property
7.8 out of 10, Good, (1002)
"We always stay here when in Baltimore."
United States
Leslie
The price is ₹9,395
₹11,039 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Hotel & Conference Center
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (923)
"Had a great stay."
United States
Melvin
The price is ₹7,302
₹8,324 total
includes taxes & fees
16 Nov - 17 Nov
Sonesta ES Suites Annapolis
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (422)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is ₹17,053
₹21,167 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
1 bedroom, hypo-allergenic bedding, desk, blackout curtains
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1018)
"Had a wonderful stay"
United States
John
The price is ₹8,525
₹9,718 total
includes taxes & fees
2 Nov - 3 Nov
Country Inn & Suites by Radisson, Annapolis, MD
Reception
Village Inn Annapolis MD
Village Inn Annapolis MD
2.0 star property
6.2 out of 10, (504)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is ₹7,302
₹8,324 total
includes taxes & fees
2 Nov - 3 Nov
Village Inn Annapolis MD
Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1863)
"The hotel was absolutely clean and close to the shops and restaurants. "
United States
Trudy
Historic Inns of Annapolis
Garden
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1019)
"Comfortable place to stay, nice shopping area close by. "
United States
Roya
The price is ₹9,242
₹10,535 total
includes taxes & fees
18 Nov - 19 Nov
DoubleTree by Hilton Hotel Annapolis
Exterior
Best Western Annapolis
Best Western Annapolis
2.5 star property
7.8 out of 10, Good, (1016)
"Clean room, nice staff and plenty of parking "
United States
Chauntese
The price is ₹6,651
₹7,582 total
includes taxes & fees
16 Nov - 17 Nov
Best Western 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 Maryland State House and William Paca 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, Ballet Theater of Maryland and Spa Creek are top sights worth seeing.

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.

Cape Saint Claire

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

Top Winchester-on-the-Severn Hotel Reviews

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

10/10 Excellent
"Great hotel!"
Shanikka 3-night trip
Posted 17 hours ago
The Hotel at Arundel Preserve

Explore a world of travel with Expedia

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.