Find hotels in Winchester-on-the-Severn, Annapolis

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

Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
14.7 mi from Winchester-on-the-Severn
9.2 out of 10, Wonderful, (922)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
$103 nightly
The price is $114
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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
18.9 mi from Winchester-on-the-Severn
8.6 out of 10, Excellent, (384)
"Friendly staff and good clean rooms."
United States
Jean
$91 nightly
The price is $107
Dec 1 - Dec 2
Total with taxes and fees
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
14.7 mi from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1002)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
$102 nightly
The price is $113
Nov 25 - Nov 26
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
14.5 mi from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (655)
"My favorite hotel "
United States
Jen
$159 nightly
The price is $176
Nov 19 - Nov 20
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Front of property
Comfort Suites Columbia Gateway

Comfort Suites Columbia Gateway

2.5 star property
18.5 mi from Winchester-on-the-Severn
8.2 out of 10, Very Good, (1006)
"Great receptionnist "
Canada
Denys
$86 nightly
The price is $97
Dec 7 - Dec 8
Total with taxes and fees
Comfort Suites Columbia Gateway
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
2.7 mi from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1002)
"Great environment"
United States
Salvador E
$154 nightly
The price is $176
Dec 14 - Dec 15
Total with taxes and fees
The Westin Annapolis
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
18.4 mi from Winchester-on-the-Severn
7.8 out of 10, Good, (1005)
"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "
United States
Carmen
$116 nightly
The price is $136
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Hotel & Conference Center
Premium bedding, pillowtop beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
3.5 mi from Winchester-on-the-Severn
8.2 out of 10, Very Good, (1005)
"I had a great experience at my stay at Hampton "
United States
Idris O
$96 nightly
The price is $109
Dec 1 - Dec 2
Total with taxes and fees
Hampton Inn & Suites Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
10.2 mi from Winchester-on-the-Severn
9.2 out of 10, Wonderful, (125)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$139 nightly
The price is $151
Dec 9 - Dec 10
Total with taxes and fees
Kent Island Resort
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3.0 star property
3.7 mi from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1004)
"Wonderful stay. "
United States
Angela
$100 nightly
The price is $114
Dec 7 - Dec 8
Total with taxes and fees
Courtyard by Marriott Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
2.8 mi from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1004)
"Clean, easy parking, nice staff but over priced breakfast"
United States
Gabrielle
$93 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
Crowne Plaza Annapolis by IHG
1 bedroom, hypo-allergenic bedding, desk, blackout drapes
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
3.3 mi from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1010)
"Wonderful country inn!"
United States
Jennifer
$93 nightly
The price is $106
Dec 9 - Dec 10
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Property amenity
Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
18.1 mi from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (694)
"Parking was easy. The property is very nice and the personel very friendly."
United States
Katia
$134 nightly
The price is $158
Nov 23 - Nov 24
Total with taxes and fees
Courtyard by Marriott Baltimore Downtown/McHenry Row
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
3.8 mi from Winchester-on-the-Severn
8.2 out of 10, Very Good, (1003)
"I had a lovely stay."
United States
Kalynn
$74 nightly
The price is $84
Dec 7 - Dec 8
Total with taxes and fees
Hilton Garden Inn Annapolis
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
3.7 mi from Winchester-on-the-Severn
8.8 out of 10, Excellent, (950)
"Nice breakfast, clean room, great parking"
United States
Amy
$83 nightly
The price is $95
Dec 7 - Dec 8
Total with taxes and fees
Sonesta ES Suites Annapolis
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District, 2.7 mi from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1896)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
$162 nightly
The price is $185
Nov 24 - Nov 25
Total with taxes and fees
Historic Inns of Annapolis
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District, 3 mi from Winchester-on-the-Severn
8.8 out of 10, Excellent, (876)
"Clean room. Friendly staff awesome location. "
United States
Brent
$160 nightly
The price is $183
Nov 30 - Dec 1
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
14.6 mi from Winchester-on-the-Severn
8.0 out of 10, Very Good, (1006)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$92 nightly
The price is $102
Nov 26 - Nov 27
Total with taxes and fees
Best Western Kent Narrows Inn
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
10.1 mi from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (426)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
$207 nightly
The price is $230
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
3.1 mi from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1007)
"Room was comfortable and the staff were courtesy!"
United States
Danny
$68 nightly
The price is $78
Nov 25 - Nov 26
Total with taxes and fees
DoubleTree by Hilton Hotel 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.

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

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

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

10/10 Excellent
"Room was in great shape. "
Richard 1-night trip
Posted 15 hours ago
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

Frequently asked questions

Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester-on-the-Severn.
How can I save on a Winchester-on-the-Severn hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchester-on-the-Severn hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winchester-on-the-Severn hotel?
Hotel prices in Winchester-on-the-Severn often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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