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

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Our top choices for Annapolis Sailing School hotels

A white two-story building with a central entrance, a staircase, and a small garden area.

1. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

NT$7,920 total

includes taxes & fees

Nov 2 - Nov 3

A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.

2. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Angela

NT$10,955 total

includes taxes & fees

Nov 1 - Nov 2

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Kathleen

NT$5,148 total

includes taxes & fees

Nov 22 - Nov 23

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Thomas

NT$8,414 total

includes taxes & fees

Nov 1 - Nov 2

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

5. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Christiaan

NT$4,297 total

includes taxes & fees

Nov 9 - Nov 10

An outdoor patio with tables, chairs, and a fire feature.

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

NT$4,999 total

includes taxes & fees

Nov 23 - Nov 24

7. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

NT$4,703 total

includes taxes & fees

Nov 15 - Nov 16

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

8. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

NT$6,278 total

includes taxes & fees

Nov 22 - Nov 23

A balcony with a table set for two, overlooking a marina with boats.

9. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

John

NT$7,969 total

includes taxes & fees

Nov 23 - Nov 24

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Joel

NT$3,442 total

includes taxes & fees

Nov 15 - Nov 16

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

NT$8,564 total

includes taxes & fees

Nov 15 - Nov 16

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Tucker

NT$3,189 total

includes taxes & fees

Nov 23 - Nov 24

A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

13. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

NT$4,370 total

includes taxes & fees

Nov 4 - Nov 5

A large, two-story barn-style building with a covered front porch and a garage.

14. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

NT$5,503 total

includes taxes & fees

Nov 17 - Nov 18

15. Laurel Grove Inn on the South

9.3 km from Annapolis Sailing School

Ruth

NT$6,687 total

includes taxes & fees

Nov 11 - Nov 12

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

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

7.4 km from Annapolis Sailing School

Isidore

NT$3,091 total

includes taxes & fees

Nov 23 - Nov 24

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

17. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

FRANK

NT$4,607 total

includes taxes & fees

Nov 22 - Nov 23

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

18. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

NT$3,320 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

19. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

NT$3,752 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

20. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Panagiotis

NT$3,158 total

includes taxes & fees

Nov 16 - Nov 17

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Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
134 Prince - Luxury Boutique Hotel	2.5 star property	9.8 Exceptional 49 reviews	View
86 State Circle - Luxury Boutique Hotel	2.0 star property	9.8 Exceptional 11 reviews	View
Graduate by Hilton Annapolis	4.0 star property	9.4 Exceptional 1,013 reviews	View
Flag House Inn	3.5 star property	9.2 Wonderful 99 reviews	View
Historic Inns of Annapolis	3.5 star property	9.0 Wonderful 2,065 reviews	View

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"N/A…………………..,,,,,,,. Xxx. Cc"

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."

Other attractions near Annapolis Sailing School

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 88 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 88 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, Hammond-Harwood House, or London Town. 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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Maryland Vacation Rentals

Find hotels near Annapolis Sailing School, Annapolis from NT$3,091

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Our top choices for Annapolis Sailing School hotels

1. 134 Prince - Luxury Boutique Hotel

2. 86 State Circle - 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. Annapolis Waterfront Hotel, Autograph Collection

10. Hilton Garden Inn Annapolis Downtown

11. The Inn at Chesapeake Bay Beach Club

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

13. TownePlace Suites by Marriott Annapolis

14. Kent Island Resort

15. Laurel Grove Inn on the South

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

17. SpringHill Suites by Marriott Annapolis

18. DoubleTree by Hilton Hotel Annapolis

19. Crowne Plaza Annapolis by IHG

20. Sonesta ES Suites Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

Other attractions near Annapolis Sailing School

Susan Campbell Park

Frequently asked questions

Explore a world of travel with Expedia