The Best Hotels Closest to Annapolis Sailing School in Annapolis for 2026

Our top choices for Annapolis Sailing School hotels

86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Jo

₩483,540 total

includes taxes & fees

Jun 8 - Jun 9

134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

₩378,672 total

includes taxes & fees

Jun 10 - Jun 11

Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

₩386,995 total

includes taxes & fees

Jun 8 - Jun 9

Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

David

₩305,876 total

includes taxes & fees

Jun 21 - Jun 22

Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Randy

₩238,570 total

includes taxes & fees

Jun 14 - Jun 15

Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

Salvatore

₩406,146 total

includes taxes & fees

Jul 1 - Jul 2

The Westin Annapolis

2.7 km from Annapolis Sailing School

Jiyoung

₩335,716 total

includes taxes & fees

Jul 2 - Jul 3

Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Eileen

₩239,798 total

includes taxes & fees

Jul 5 - Jul 6

Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Joshua

₩269,994 total

includes taxes & fees

Jul 5 - Jul 6

Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Victoria

₩246,157 total

includes taxes & fees

Jun 21 - Jun 22

Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Mehran

₩201,311 total

includes taxes & fees

Jun 9 - Jun 10

SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Daniel Glen Zechenelly

₩255,162 total

includes taxes & fees

Jun 21 - Jun 22

TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Cheryl

₩209,602 total

includes taxes & fees

Jun 14 - Jun 15

Country Inn & Suites by Radisson, Annapolis, MD

7.4 km from Annapolis Sailing School

David

₩179,670 total

includes taxes & fees

Jun 21 - Jun 22

DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

William

₩194,680 total

includes taxes & fees

Jun 10 - Jun 11

Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jeffrey

₩216,706 total

includes taxes & fees

Jun 21 - Jun 22

Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Michele

₩190,249 total

includes taxes & fees

Jun 10 - Jun 11

Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Anne

₩225,588 total

includes taxes & fees

Jun 21 - Jun 22

Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout drapes

Holiday Inn Express & Suites Annapolis by IHG

6 km from Annapolis Sailing School

Margaret

₩225,588 total

includes taxes & fees

Jun 14 - Jun 15

The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

Winfred

₩429,837 total

includes taxes & fees

Jun 15 - Jun 16

View all properties

Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
86 State Circle - Luxury Boutique Hotel	2.0 star property	10.0 Exceptional 5 reviews	View
134 Prince - Luxury Boutique Hotel	2.5 star property	9.8 Exceptional 37 reviews	View
Flag House Inn	3.5 star property	9.2 Wonderful 94 reviews	View
Graduate by Hilton Annapolis	4.0 star property	9.2 Wonderful 1,004 reviews	View
Historic Inns of Annapolis	3.5 star property	9.0 Wonderful 1,864 reviews	View

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"A great place in the heart of Annapolis! It’s very historic and a great atmosphere. My only gripe was that the bathroom windows didn’t open which made the bathroom way too and humid after showering but other than that, it was great!"

Hilton Garden Inn Annapolis Downtown

6/10 Okay

"Day and Evening front desk staff were friendly, courteous and helpful. The room itself as well as the general condition of the hotel, luggage carts, ice dispensers, carpet condition, especially in room were torn, worn and in need of repair or replacement. The bathroom has peeling wall paper, the refrigerators had broken door rails and the first one we had, froze everything in it on the first day we were there. The exhaust fans in the bathroom operate on their own accord and would cut on with any motion, even coming into the room sometimes. They are old motors, with rattling and a constant loud hum, and the first night stayed on till 5am, the second night till 3am in the morning. After calling the nightstaff, was told "they will eventually cut off". Spoke with the general manager and was moved on the 3rd day to a quiter room in better condition. The fan had to be disconnected, as it was said to have no manual controls. This was a long standing problem, as it appears many guest have complained before, and no one has sought to put a manual switch in the rooms."

Graduate by Hilton Annapolis

8/10 Good

"Everything was good. Only negative was the girl At the coffee shop in the lobby. She put two medium coffees on counter and announced “two medium coffees” and neither the guy next to me or myself realized each was for one of us bc we assumed it was for someone who ordered TWO bc that’s how she announced it. The. Seemed irritated that we didn’t get it. Oh and parking was not extremely convenient but still cost 35 bucks."

Hotels near other Annapolis Sailing School attractions

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.

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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 89 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 0.8 mi (1.4 km) from Annapolis Sailing School. Other good choices within 5 miles include Historic Inns of Annapolis and Graduate by Hilton Annapolis.

How many hotels are there near Annapolis Sailing School?

Expedia has 89 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, Kunta Kinte Plaque & Alex Haley Memorial, and Maynard-Burgess House. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.

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Our top choices for Annapolis Sailing School hotels

86 State Circle - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

Flag House Inn

Graduate by Hilton Annapolis

Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Residence Inn By Marriott Annapolis

Hilton Garden Inn Annapolis Downtown

Candlewood Suites Annapolis by IHG

SpringHill Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

DoubleTree by Hilton Hotel Annapolis

Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

Courtyard by Marriott Annapolis

Holiday Inn Express & Suites Annapolis by IHG

The Inn at Chesapeake Bay Beach Club

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

Hotels near other Annapolis Sailing School attractions

Susan Campbell Park

Frequently asked questions