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

AED 893 total

includes taxes & fees

8 Nov - 9 Nov

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

AED 1,027 total

includes taxes & fees

11 Nov - 12 Nov

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

3. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Thomas

AED 951 total

includes taxes & fees

8 Nov - 9 Nov

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

4. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Christiaan

AED 575 total

includes taxes & fees

27 Nov - 28 Nov

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

5. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

AED 565 total

includes taxes & fees

23 Nov - 24 Nov

6. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

AED 532 total

includes taxes & fees

10 Nov - 11 Nov

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

7. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

AED 708 total

includes taxes & fees

22 Nov - 23 Nov

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

8. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

John

AED 935 total

includes taxes & fees

29 Nov - 30 Nov

9. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Joel

AED 432 total

includes taxes & fees

2 Dec - 3 Dec

10. Laurel Grove Inn on the South

9.3 km from Annapolis Sailing School

Ruth

AED 754 total

includes taxes & fees

11 Nov - 12 Nov

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

AED 845 total

includes taxes & fees

2 Dec - 3 Dec

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

AED 363 total

includes taxes & fees

15 Nov - 16 Nov

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

13. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

AED 620 total

includes taxes & fees

18 Nov - 19 Nov

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

14. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

FRANK

AED 424 total

includes taxes & fees

29 Nov - 30 Nov

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

15. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

AED 423 total

includes taxes & fees

22 Nov - 23 Nov

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

Michael

AED 365 total

includes taxes & fees

29 Nov - 30 Nov

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

17. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

AED 374 total

includes taxes & fees

10 Nov - 11 Nov

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

18. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

AED 423 total

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a large window, a dining area, and a kitchen in the background.

19. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Jose

AED 370 total

includes taxes & fees

29 Nov - 30 Nov

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

AED 343 total

includes taxes & fees

29 Nov - 30 Nov

View all properties

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 51 reviews	View
86 State Circle - Luxury Boutique Hotel	2.0 star property	9.8 Exceptional 12 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 2,057 reviews	View
Residence Inn By Marriott Annapolis	3.0 star property	9.0 Wonderful 95 reviews	View

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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Top Annapolis Sailing School Hotel Reviews

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

86 State Circle - Luxury Boutique Hotel

Historic District

10/10 Excellent

MARA

A house with a porch, a red umbrella, and a garden with pink flowers.

Inn at Horn Point

Eastport

10/10 Excellent

ronald

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Celina

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.

Sheree

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.

Find hotels near Annapolis Sailing School, Annapolis from AED 379

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Annapolis Sailing School hotels

1. 134 Prince - Luxury Boutique Hotel

2. 86 State Circle - Luxury Boutique Hotel

3. Flag House Inn

4. Historic Inns of Annapolis

5. Residence Inn By Marriott Annapolis

6. Fairfield Inn & Suites By Marriott Annapolis

7. The Westin Annapolis

8. Annapolis Waterfront Hotel, Autograph Collection

9. Hilton Garden Inn Annapolis Downtown

10. Laurel Grove Inn on the South

11. The Inn at Chesapeake Bay Beach Club

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

13. Kent Island Resort

14. SpringHill Suites by Marriott Annapolis

15. TownePlace Suites by Marriott Annapolis

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

17. DoubleTree by Hilton Hotel Annapolis

18. Crowne Plaza Annapolis by IHG

19. Candlewood Suites Annapolis by IHG

20. Sonesta ES Suites Annapolis

Compare popular hotels close to Annapolis Sailing School

Other attractions near Annapolis Sailing School

Susan Campbell Park

Top Annapolis Sailing School Hotel Reviews

134 Prince - Luxury Boutique Hotel

10/10 Excellent

Frequently Asked Questions

What's the area like around Annapolis Sailing School?

What's the best hotel to stay near Annapolis Sailing School?

How many hotels are there near Annapolis Sailing School?

If I need to cancel the hotel reservation for my stay near Annapolis Sailing School, will I receive a refund?

Where can I learn more about changing or cancelling my trip in the area near Annapolis Sailing School?

What can I see and do near Annapolis Sailing School?