Find hotels in Winchester-on-the-Severn, Annapolis from ₩133,066

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Discover 1,275 Winchester-on-the-Severn hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is ₩179,033
₩198,726 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (629)
"Great location and rooms. Great place!"
The price is ₩210,047
₩233,152 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (999)
"Hotel was great, beautiful location near the water"
The price is ₩222,058
₩246,484 total
includes taxes & fees
Oct 5 - Oct 6
Hilton Garden Inn Kent Island 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, (331)
"Great Place Places to Stay "
The price is ₩122,645
₩144,109 total
includes taxes & fees
Oct 1 - Oct 2
Holiday Inn Express Baltimore At The Stadiums by IHG
Comfort Suites Columbia Gateway
Front of property

Comfort Suites Columbia Gateway

2.5 star property
8.2 out of 10, Very Good, (1002)
"Staff at this place were very nice "
The price is ₩125,605
₩141,935 total
includes taxes & fees
Oct 5 - Oct 6
Comfort Suites Columbia Gateway
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1008)
"Would stay there again very soon "
The price is ₩280,532
₩319,807 total
includes taxes & fees
Sep 28 - Sep 29
The Westin Annapolis
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is ₩266,435
₩348,691 total
includes taxes & fees
Oct 21 - Oct 22
Kent Island Resort
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 hotel "
The price is ₩163,089
₩191,631 total
includes taxes & fees
Oct 1 - Oct 2
Best Western Plus Hotel & Conference Center
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1000)
"The room was great, and the staff was great. "
The price is ₩160,707
₩183,206 total
includes taxes & fees
Oct 20 - Oct 21
Courtyard by Marriott Annapolis
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1001)
"Excellent location"
The price is ₩178,216
₩197,819 total
includes taxes & fees
Oct 5 - Oct 6
Best Western Kent Narrows Inn
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (831)
"Great place and great staff"
The price is ₩145,834
₩161,876 total
includes taxes & fees
Oct 19 - Oct 20
Quality Inn
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, (665)
"I liked that it was conveniently next to a grocery store. I also liked that the rooms were spacious and appeared to be soundproof. "
The price is ₩189,042
₩222,125 total
includes taxes & fees
Oct 19 - Oct 20
Courtyard by Marriott Baltimore Downtown/McHenry Row
Sonesta ES Suites Annapolis
Egyptian cotton sheets, premium bedding, pillowtop beds, desk

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (897)
"Had a great stay."
The price is ₩149,711
₩170,673 total
includes taxes & fees
Sep 28 - Sep 29
Sonesta ES Suites Annapolis
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, (1014)
"Nice location and staff was friendly and helpful."
The price is ₩161,243
₩183,817 total
includes taxes & fees
Oct 19 - Oct 20
Hampton Inn & Suites Annapolis
Anchored Inn at Hidden Harbour Marina
Front of property

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (454)
"Very clean and fresh!❤️Loved the room. bar loud at happy hour outside . Food good at food truck. Would for sure stay again, looking forward to our next stay at anchored inn."
The price is ₩252,479
₩287,835 total
includes taxes & fees
Sep 28 - Sep 29
Anchored Inn at Hidden Harbour Marina
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, (1022)
"Great place to stay. The pool and hot tub are great amenities. "
The price is ₩142,592
₩162,555 total
includes taxes & fees
Oct 14 - Oct 15
Country Inn & Suites by Radisson, Annapolis, MD
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, (420)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is ₩288,991
₩356,644 total
includes taxes & fees
Oct 26 - Oct 27
The Inn at Chesapeake Bay Beach Club
Crowne Plaza Annapolis by IHG
Indoor pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1018)
"Good location"
The price is ₩157,888
₩179,992 total
includes taxes & fees
Oct 14 - Oct 15
Crowne Plaza Annapolis by IHG
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1856)
"Perfect location…terrific staff…spacious room with a king sized bed! "
The price is ₩157,958
₩228,283 total
includes taxes & fees
Oct 27 - Oct 28
Historic Inns of Annapolis
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1019)
"Friendly staff with a good breakfast"
The price is ₩116,724
₩133,066 total
includes taxes & fees
Sep 30 - Oct 1
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.
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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.
Annapolis which includes street scenes and a city as well as a small group of people

Historic District

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

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

Murray Hill

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

Maryland Quiet Waters Park featuring a garden and a house

Hillsmere

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

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.

Top Winchester-on-the-Severn Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"."
Kenneth 1-night trip
Posted 2 days ago
Best Western Plus Hotel & Conference Center

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Explore a world of travel with Expedia

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.