Find hotels near Annapolis Sailing School, Annapolis from ￥13,545

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Dec 14 - Dec 15
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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Our top choices for Annapolis Sailing School hotels

Lobby lounge
Flag House Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District, 1.7 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (83)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is ￥28,493
￥32,482 total
includes taxes & fees
Dec 16 - Dec 17
Flag House Inn
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
2.3 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is ￥20,793
￥23,704 total
includes taxes & fees
Dec 22 - Dec 23
Graduate by Hilton Annapolis
Meeting facility
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District, 1.9 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (1900)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Terrace/patio
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
3 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (165)
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is ￥17,139
￥19,539 total
includes taxes & fees
Dec 19 - Dec 20
Fairfield Inn & Suites By Marriott Annapolis
Terrace/patio
Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3.0 star property
3 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (54)
"had a great stay staff was fabulous room was perfect for our needs location was convenient to shopping and restaurants"
United States
karen c.
The price is ￥19,788
￥22,558 total
includes taxes & fees
Dec 21 - Dec 22
Residence Inn By Marriott Annapolis
Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District, 1.4 km from Annapolis Sailing School
8.8 out of 10, Excellent, (882)
"Great location, nice and clean "
United States
Micah
The price is ￥27,680
￥31,555 total
includes taxes & fees
Dec 21 - Dec 22
Annapolis Waterfront Hotel, Autograph Collection
Lobby
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
2.5 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1008)
"Great value for stay with breakfast included "
United States
Aisling
The price is ￥12,340
￥14,067 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Annapolis Downtown
Property amenity
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
2.7 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is ￥23,995
￥27,355 total
includes taxes & fees
Dec 15 - Dec 16
The Westin Annapolis
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
1.6 km from Annapolis Sailing School
9.8 out of 10, Exceptional, (31)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Bar (on property)
86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District, 2 km from Annapolis Sailing School
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is ￥51,294
￥58,476 total
includes taxes & fees
Dec 15 - Dec 16
86 State Circle - Luxury Boutique Hotel
BBQ/picnic area
TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
3.0 star property
6.6 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (50)
"The staff was welcoming, the room was very clean and comfortable and tue pocation waa great."
United States
Karen
The price is ￥14,490
￥16,519 total
includes taxes & fees
Jan 11 - Jan 12, 2026
TownePlace Suites by Marriott Annapolis
Free daily self-serve breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
6.4 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (1002)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is ￥15,760
￥17,967 total
includes taxes & fees
Dec 22 - Dec 23
SpringHill Suites by Marriott Annapolis
Lobby
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
7.3 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (1003)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is ￥14,833
￥16,909 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Exterior
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
6.2 km from Annapolis Sailing School
8.8 out of 10, Excellent, (180)
"Nice staff, clean room, comfortable bed. "
United States
Jayne
The price is ￥13,088
￥14,920 total
includes taxes & fees
Dec 19 - Dec 20
Candlewood Suites Annapolis by IHG
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
6.3 km from Annapolis Sailing School
8.8 out of 10, Excellent, (1002)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is ￥16,516
￥18,828 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Crowne Plaza Annapolis by IHG
Free daily buffet breakfast
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
6.6 km from Annapolis Sailing School
8.8 out of 10, Excellent, (963)
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is ￥14,179
￥16,164 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sonesta ES Suites Annapolis
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
13 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (430)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is ￥28,645
￥35,760 total
includes taxes & fees
Dec 18 - Dec 19
The Inn at Chesapeake Bay Beach Club
Reception
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
6.3 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1006)
"Great place!"
United States
Tawnya
The price is ￥11,882
￥13,545 total
includes taxes & fees
Dec 28 - Dec 29
DoubleTree by Hilton Hotel Annapolis
Property amenity
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
6.8 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1002)
"Wonderful stay. "
United States
Angela
The price is ￥13,088
￥14,920 total
includes taxes & fees
Dec 29 - Dec 30
Courtyard by Marriott Annapolis
Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
13.1 km from Annapolis Sailing School
9.2 out of 10, Wonderful, (128)
"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
The price is ￥22,291
￥30,309 total
includes taxes & fees
Dec 16 - Dec 17
Kent Island Resort
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

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 3 days ago
Historic Inns of Annapolis

Hotels near other Annapolis Sailing School attractions

Annapolis Harbor
Photo by Michael Lore
Open Photo by Michael Lore

Susan Campbell Park

Susan Campbell Park is just one of the places to see in Annapolis, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties
Ego Alley

Ego Alley

Explore the waterfront in Annapolis with a trip to Ego Alley. While you're here, you can savor the top-notch restaurants.
See properties

Frequently asked questions

What's the area like around Annapolis Sailing School?
Annapolis Sailing School is located in an area of Annapolis known for its interesting historical sites. If you're looking for a convenient place to stay, check out the 99 hotels and other accommodations you'll find within a mile.
What's the best hotel to stay near Annapolis Sailing School?
Annapolis Waterfront Hotel, Autograph Collection is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and a 24-hour fitness center. It's located just a short 0.9 mi (1.4 km) from Annapolis Sailing School. Other good choices within 5 miles include Historic Inns of Annapolis and Hilton Garden Inn Annapolis Downtown.
How many hotels are there near Annapolis Sailing School?
Expedia has 99 hotels and other accommodations within a mile from Annapolis Sailing School.
If I need to cancel the hotel reservation for my stay near Annapolis Sailing School, will I receive a refund?
Yes, most room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to review the best deals near Annapolis Sailing School.
Where can I learn more about changing or cancelling my trip in the area near Annapolis Sailing School?
To access more information about picking new dates or cancelling your stay near Annapolis Sailing School, go to https://www.expedia.com/service/.
What can I see and do near Annapolis Sailing School?
Study the collections at Annapolis Maritime Museum, London Town, or Hammond-Harwood House. Explore landmarks like William Paca House, 97, 99 and 101 East Street, and Kunta Kinte Plaque & Alex Haley Memorial. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.

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