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

Our top choices for Annapolis Sailing School hotels

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Jo

￥65,517 total

includes taxes & fees

Jul 21 - Jul 22

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

￥39,468 total

includes taxes & fees

Jul 21 - Jul 22

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Gabriela

￥30,999 total

includes taxes & fees

Jul 26 - Jul 27

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Tyler

￥40,335 total

includes taxes & fees

Jul 21 - Jul 22

5. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Caitlin

￥26,657 total

includes taxes & fees

Aug 3 - Aug 4

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

￥28,141 total

includes taxes & fees

Jul 26 - Jul 27

7. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Eileen

￥24,993 total

includes taxes & fees

Jul 26 - Jul 27

8. The Westin Annapolis

2.7 km from Annapolis Sailing School

Jessica

￥36,842 total

includes taxes & fees

Jul 26 - Jul 27

9. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Tammy

￥21,142 total

includes taxes & fees

Aug 3 - Aug 4

10. Kent Island Resort

13.1 km from Annapolis Sailing School

Leigh

￥31,992 total

includes taxes & fees

Aug 6 - Aug 7

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

Damika

￥46,596 total

includes taxes & fees

Aug 2 - Aug 3

12. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Jamila

￥21,846 total

includes taxes & fees

Jul 26 - Jul 27

13. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Zhun Wha

￥23,883 total

includes taxes & fees

Jul 26 - Jul 27

14. Country Inn & Suites by Radisson, Annapolis, MD

7.4 km from Annapolis Sailing School

Lawrence

￥20,301 total

includes taxes & fees

Aug 3 - Aug 4

15. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Lena

￥21,102 total

includes taxes & fees

Aug 19 - Aug 20

16. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jane

￥21,846 total

includes taxes & fees

Aug 2 - Aug 3

17. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Mehran

￥17,044 total

includes taxes & fees

Jul 27 - Jul 28

18. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Craig

￥21,160 total

includes taxes & fees

Aug 2 - Aug 3

19. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Tyriek

￥23,883 total

includes taxes & fees

Jul 22 - Jul 23

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

20. Holiday Inn Express & Suites Annapolis by IHG

6 km from Annapolis Sailing School

Jaime

￥17,797 total

includes taxes & fees

Jul 26 - Jul 27

View all properties

Compare popular hotels close to Annapolis Sailing School

Property	Star rating	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 1,005 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 1,891 reviews	View

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

8/10 Good

"The Hilton was a very nice hotel close to Downtown Annapolis. The staff was very helpful and our room was nice. $35 to park is a bit steep and I think there are other parking garages within a short walk that might have been less expensive so I recommend looking into that if you are on a budget. Overall a good experience."

Beachfront Home Minutes to Downtown Annapolis Dogs OK

10/10 Excellent

"We had a wonderful stay at this charming waterfront home! While the house is older, it has so much character and was incredibly comfortable. The location is unbeatable—the peaceful waterfront views and beautiful sunsets made every day special. The home was clean, cozy, and had everything we needed for a relaxing getaway. If you’re looking for a place with charm, comfort, and an amazing setting rather than a modern luxury property, this is the perfect spot. We would absolutely stay here again and highly recommend it!"

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.

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 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

1. 86 State Circle - Luxury Boutique Hotel

2. 134 Prince - Luxury Boutique Hotel

3. Graduate by Hilton Annapolis

4. Flag House Inn

5. Historic Inns of Annapolis

6. Residence Inn By Marriott Annapolis

7. Fairfield Inn & Suites By Marriott Annapolis

8. The Westin Annapolis

9. Hilton Garden Inn Annapolis Downtown

10. Kent Island Resort

11. The Inn at Chesapeake Bay Beach Club

12. TownePlace Suites by Marriott Annapolis

13. SpringHill Suites by Marriott Annapolis

14. Country Inn & Suites by Radisson, Annapolis, MD

15. DoubleTree by Hilton Hotel Annapolis

16. Crowne Plaza Annapolis by IHG

17. Candlewood Suites Annapolis by IHG

18. Sonesta ES Suites Annapolis

19. Courtyard by Marriott Annapolis

20. Holiday Inn Express & Suites Annapolis by IHG

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