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 1,505 total

includes taxes & fees

21 Jul - 22 Jul

134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

AED 893 total

includes taxes & fees

21 Jul - 22 Jul

Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Gabriela

AED 694 total

includes taxes & fees

27 Jul - 28 Jul

Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Tyler

AED 912 total

includes taxes & fees

21 Jul - 22 Jul

Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Caitlin

AED 603 total

includes taxes & fees

12 Aug - 13 Aug

Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

AED 636 total

includes taxes & fees

26 Jul - 27 Jul

The Westin Annapolis

2.7 km from Annapolis Sailing School

Jessica

AED 833 total

includes taxes & fees

26 Jul - 27 Jul

Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Eileen

AED 565 total

includes taxes & fees

26 Jul - 27 Jul

Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Victoria

AED 467 total

includes taxes & fees

16 Aug - 17 Aug

TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Cheryl

AED 494 total

includes taxes & fees

26 Jul - 27 Jul

The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

Damika

AED 1,054 total

includes taxes & fees

2 Aug - 3 Aug

Kent Island Resort

13.1 km from Annapolis Sailing School

Leigh

AED 724 total

includes taxes & fees

5 Aug - 6 Aug

SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Zhun Wha

AED 540 total

includes taxes & fees

26 Jul - 27 Jul

Country Inn & Suites by Radisson, Annapolis, MD

7.4 km from Annapolis Sailing School

Theresa

AED 459 total

includes taxes & fees

3 Aug - 4 Aug

Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Mehran

AED 397 total

includes taxes & fees

2 Aug - 3 Aug

Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jeffrey

AED 494 total

includes taxes & fees

2 Aug - 3 Aug

DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Lena

AED 477 total

includes taxes & fees

20 Aug - 21 Aug

Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Craig

AED 482 total

includes taxes & fees

2 Aug - 3 Aug

Microtel Inn & Suites by Wyndham Gambrills

19.7 km from Annapolis Sailing School

Patrick

AED 409 total

includes taxes & fees

16 Aug - 17 Aug

Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Tyriek

AED 444 total

includes taxes & fees

27 Jul - 28 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 7 reviews	View
134 Prince - Luxury Boutique Hotel	2.5 star property	9.8 Exceptional 38 reviews	View
Graduate by Hilton Annapolis	4.0 star property	9.4 Exceptional 1,004 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 1,890 reviews	View

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"The hotel was very conveniently located but since it was right downtown, the rooms were a little small."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"The hotel is lovely and right in the heart of everything. We walked to each meal and walked even further for exercise. The room was clean and had all that we needed aside from some missing toiletries. As busy as the hotel was, the noise was contained and did not bother us. Overall a great stay and we will definitely choose this hotel in the future."

Beautiful Condo - Water View Near City Dock

10/10 Excellent

"This little apartment was perfect for the two of us. The location was within walking distance to historic downtown Annapolis. There are many fun restaurants within walking distance as well. We spent one day at Quiet Waters Park for a family gathering. This is a beautiful park with shaded paved trails, and water views. There is also fenced dog park and even a dog beach."

2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

10/10 Excellent

"My girlfriends and I take a long trip every year to a different city. We are at a point in our lives where we have very high standards and this beautiful home met all of our needs and more! It is in a quiet Eastport neighborhood, with approximately 8 to 10 minute walk to the heart of Annapolis. We each had our own bedroom and there were three full bathrooms (each with a bidet!!) and an outdoor shower. The living space was beautifully decorated and very spacious. The kitchen was updated and was a lovely space to create our happy hour snacks and our morning meals. The outdoor deck and patio with fire pit were fantastic for our late night wine talks! Because we go out for dinner every night, we didn't use the dining room but for people who want to cook and eat in, it is the perfect space! They even had a music room with piano and a guitar for the musically inclined. The entire house was super clean! There is a driveway right beside the home. We parked our car and unpacked and didn't start it until we left. The location is extremely walkable to everything. We had a minor issue on the first night with one of the toilets, and the host responded super fast. The handyman fixed the problem and was super sweet as well. The experience we had with this rental was incredible, and we would definitely stay here again on a future trip to Annapolis. Highly recommend!!!"

Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

10/10 Excellent

"This property was truly a wonderful place to stay! It is beautiful, well-kept with great amenities (jacuzzi tub, barbecue pit, private driveway, etc.), and we were very cozy and comfortable. The view of the Chesapeake Bay from the primary bedroom is breathtaking! Also, the location in Eastport with its great restaurants which is within walking distance to Annapolis and the US Naval Academy is very convenient. We highly recommend staying at this property for a wonderful get away!"

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 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

Graduate by Hilton Annapolis

Flag House Inn

Historic Inns of Annapolis

Residence Inn By Marriott Annapolis

The Westin Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Hilton Garden Inn Annapolis Downtown

TownePlace Suites by Marriott Annapolis

The Inn at Chesapeake Bay Beach Club

Kent Island Resort

SpringHill Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Candlewood Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Sonesta ES Suites Annapolis

Microtel Inn & Suites by Wyndham Gambrills

Courtyard by Marriott Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hotels near other Annapolis Sailing School attractions

Susan Campbell Park

Frequently asked questions

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