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

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Our top choices for Annapolis Sailing School hotels

86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Jo

AED 996 total

includes taxes & fees

1 Jul - 2 Jul

134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

AED 780 total

includes taxes & fees

1 Jul - 2 Jul

Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

AED 912 total

includes taxes & fees

1 Jul - 2 Jul

Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Randy

AED 503 total

includes taxes & fees

6 Jul - 7 Jul

Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

David

AED 673 total

includes taxes & fees

6 Jul - 7 Jul

Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Victoria

AED 476 total

includes taxes & fees

19 Jul - 20 Jul

The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

Damika

AED 1,013 total

includes taxes & fees

6 Jul - 7 Jul

Kent Island Resort

13.1 km from Annapolis Sailing School

Sue

AED 728 total

includes taxes & fees

5 Jul - 6 Jul

SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Daniel Glen Zechenelly

AED 519 total

includes taxes & fees

5 Jul - 6 Jul

TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Cheryl

AED 494 total

includes taxes & fees

12 Jul - 13 Jul

Country Inn & Suites by Radisson, Annapolis, MD

7.4 km from Annapolis Sailing School

Theresa

AED 459 total

includes taxes & fees

12 Jul - 13 Jul

Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Mehran

AED 466 total

includes taxes & fees

7 Jul - 8 Jul

Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jeffrey

AED 477 total

includes taxes & fees

12 Jul - 13 Jul

Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Michele

AED 415 total

includes taxes & fees

1 Jul - 2 Jul

DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Diane

AED 399 total

includes taxes & fees

5 Jul - 6 Jul

Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

AED 444 total

includes taxes & fees

6 Jul - 7 Jul

Microtel Inn & Suites by Wyndham Gambrills

19.7 km from Annapolis Sailing School

Erin

AED 427 total

includes taxes & fees

12 Jul - 13 Jul

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

AED 461 total

includes taxes & fees

5 Jul - 6 Jul

Hampton Inn & Suites Annapolis

6.4 km from Annapolis Sailing School

Robert Y. Vaughn

AED 434 total

includes taxes & fees

5 Jul - 6 Jul

Hilton Garden Inn Annapolis

6.9 km from Annapolis Sailing School

Paul

AED 374 total

includes taxes & fees

6 Jul - 7 Jul

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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 6 reviews	View
134 Prince - Luxury Boutique Hotel	2.5 star property	9.8 Exceptional 38 reviews	View
Flag House Inn	3.5 star property	9.2 Wonderful 94 reviews	View
Historic Inns of Annapolis	3.5 star property	9.0 Wonderful 1,877 reviews	View
Graduate by Hilton Annapolis	4.0 star property	9.4 Exceptional 1,003 reviews	View

Top Annapolis Sailing School Hotel Reviews

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10/10 Excellent

"Beautiful home with a spectacular Zen garden and pool right in the heart of Eastport. Restaurants within walking distance. Cannot beat the location."

Historic Inns of Annapolis

10/10 Excellent

"I loved the building. It’s in a lovely spot a block from the bay so shops and restaurants are right out the front door. The building I stayed in was terrific. The only bummer, was my room was quite small, so I would advise not staying in room 1408. It was the smallest room I’ve ever stayed in. I arrived late at night as was too tired to call for my car and go back to the office to change rooms. That said it was quiet so I slept well."

Dog-Friendly Annapolis Apartment | Parking, Private Backyard & Walkable to Shops and Restaurants

10/10 Excellent

"I stayed at Below Deck for 2 weeks and had an amazing time staying at this home. I work from home so I spent the weekdays working and then would explore the town and waterways every day after work - so much to do in Annapolis in the summer, especially for water sport lovers! The backyard and deck setup was so nice for grilling and hanging out with my dogs. The bed was comfortable. The kitchen was stocked with everything you’d need. I’ll definitely be returning!"

Inn at Horn Point

10/10 Excellent

"My fiance Kevin and I stayed at the Inn at Horn Point for a weekend to explore Annapolis and relax. This Inn was our favorite part of the stay. It was cozy, chic, quiet, comfortable and elevated at the same time. Corey and Carol were both so friendly, and treated us like old friends. The breakfast was amazing!!! I also went to sleep looking forward to the coffee in the morning. It was an easy and nice walk into town to do some of the touristy stuff, but we were glad to have a place like this at the end of the night."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."

Hotels near other Annapolis Sailing School attractions

A marina with boats docked, wooden pilings, and a clear sky.

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 87 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 87 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, Maynard-Burgess House, and Kunta Kinte Plaque & Alex Haley Memorial. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.

Find hotels near Annapolis Sailing School, Annapolis from AED 374

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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

Historic Inns of Annapolis

Graduate by Hilton Annapolis

Hilton Garden Inn Annapolis Downtown

The Inn at Chesapeake Bay Beach Club

Kent Island Resort

SpringHill Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Candlewood Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

Microtel Inn & Suites by Wyndham Gambrills

Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Hilton Garden Inn Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Hotels near other Annapolis Sailing School attractions

Susan Campbell Park

Frequently asked questions

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Hotels near popular Annapolis Attractions

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