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 church with a spire, surrounded by trees and illuminated by warm lights.

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Angela

NT$8,705 total

includes taxes & fees

Nov 18 - Nov 19

A two-story white building with a central entrance, steps, and a pink door.

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

NT$7,986 total

includes taxes & fees

Nov 16 - Nov 17

A spacious atrium with a high ceiling, skylights, and a patterned floor.

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

REBECCA

NT$4,884 total

includes taxes & fees

Nov 29 - Nov 30

A dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Thomas

NT$8,512 total

includes taxes & fees

Nov 15 - Nov 16

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$3,794 total

includes taxes & fees

Nov 23 - Nov 24

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

NT$4,758 total

includes taxes & fees

Nov 24 - Nov 25

A modern living room with a fireplace, a sofa, and a coffee table.

7. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

NT$4,458 total

includes taxes & fees

Nov 24 - Nov 25

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

Donna

NT$8,062 total

includes taxes & fees

Nov 23 - Nov 24

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

9. The Westin Annapolis

2.7 km from Annapolis Sailing School

Loraine

NT$5,957 total

includes taxes & fees

Nov 15 - Nov 16

A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Joel

NT$3,656 total

includes taxes & fees

Nov 22 - Nov 23

A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

NT$7,439 total

includes taxes & fees

Dec 9 - Dec 10

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

12. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

NT$5,550 total

includes taxes & fees

Dec 1 - Dec 2

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

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

7.4 km from Annapolis Sailing School

Joel

NT$3,267 total

includes taxes & fees

Dec 6 - Dec 7

A modern hotel room with a sofa set, armchairs, a coffee table, and a TV mounted on the wall.

14. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Abby

NT$3,784 total

includes taxes & fees

Nov 22 - Nov 23

A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

15. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

FRANK

NT$4,459 total

includes taxes & fees

Nov 29 - Nov 30

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

16. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

michel demanche

NT$3,348 total

includes taxes & fees

Nov 23 - Nov 24

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

17. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Panagiotis

NT$3,147 total

includes taxes & fees

Nov 24 - Nov 25

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

NT$3,859 total

includes taxes & fees

Dec 13 - Dec 14

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

Ivette

NT$3,147 total

includes taxes & fees

Nov 22 - Nov 23

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

20. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Christopher

NT$3,759 total

includes taxes & fees

Nov 29 - Nov 30

View all properties

Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
86 State Circle - Luxury Boutique Hotel	2.0 star property	9.8 Exceptional 12 reviews	View
134 Prince - Luxury Boutique Hotel	2.5 star property	9.8 Exceptional 52 reviews	View
Graduate by Hilton Annapolis	4.0 star property	9.2 Wonderful 1,014 reviews	View
Flag House Inn	3.5 star property	9.2 Wonderful 101 reviews	View
Historic Inns of Annapolis	3.5 star property	9.0 Wonderful 2,065 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.

See properties

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

Laurel Grove Inn on the South

Annapolis

10/10 Excellent

Marti

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

10/10 Excellent

Anonymous traveler

TownePlace Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Abby

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

Fairfield Inn & Suites By Marriott Annapolis

Annapolis

10/10 Excellent

Property opened 5/2024. Still pristine when I visited with my fam. Free breakfast was very good. Gym is as you would expect in a Marriott- great. Staff working out some kinks in the check in process. Understandable to me as this is a new team. Nasty surprise when we checked in to learn there was a $30 parking fee. The lot is self park and an open lot. This was not disclosed when I booked on Expedia. I will not return to this property for this reason.

ronald

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

Candlewood Suites Annapolis by IHG

Annapolis

10/10 Excellent

Ivette

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Robert

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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Find hotels near Annapolis Sailing School, Annapolis from NT$2,342

Check prices for these dates

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Property class

Guest rating

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. Annapolis Waterfront Hotel, Autograph Collection

9. The Westin Annapolis

10. Hilton Garden Inn Annapolis Downtown

11. The Inn at Chesapeake Bay Beach Club

12. Kent Island Resort

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

14. TownePlace Suites by Marriott Annapolis

15. SpringHill Suites by Marriott Annapolis

16. DoubleTree by Hilton Hotel Annapolis

17. Sonesta ES Suites Annapolis

18. Crowne Plaza Annapolis by IHG

19. Candlewood Suites Annapolis by IHG

20. Courtyard by Marriott 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?

Explore a world of travel with Expedia