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 963 total

includes taxes & fees

11 Nov - 12 Nov

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

AED 546 total

includes taxes & fees

29 Nov - 30 Nov

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

AED 912 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.

5. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Christiaan

AED 435 total

includes taxes & fees

6 Dec - 7 Dec

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

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

AED 565 total

includes taxes & fees

23 Nov - 24 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

15 Nov - 16 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

Donna

AED 901 total

includes taxes & fees

23 Nov - 24 Nov

9. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

AED 532 total

includes taxes & fees

10 Nov - 11 Nov

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Joel

AED 443 total

includes taxes & fees

22 Nov - 23 Nov

11. 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.

12. 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.

13. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Tucker

AED 370 total

includes taxes & fees

15 Nov - 16 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 hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

16. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

AED 374 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.

17. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Jose

AED 370 total

includes taxes & fees

15 Nov - 16 Nov

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

18. 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 modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

19. Holiday Inn Express & Suites Annapolis by IHG

6 km from Annapolis Sailing School

Marc

AED 368 total

includes taxes & fees

23 Nov - 24 Nov

A modern lobby with a reception desk, seating area, and potted plants.

20. Hilton Garden Inn Annapolis

6.9 km from Annapolis Sailing School

Walter

AED 365 total

includes taxes & fees

17 Nov - 18 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
Graduate by Hilton Annapolis	4.0 star property	9.4 Exceptional 1,007 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 2,059 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

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

Inn at Horn Point

Eastport

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...

Allison J

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

Jamila

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

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

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

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

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.

Find hotels near Annapolis Sailing School, Annapolis from AED 270

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. Graduate by Hilton Annapolis

4. Flag House Inn

5. Historic Inns of Annapolis

6. Residence Inn By Marriott Annapolis

7. The Westin Annapolis

8. Annapolis Waterfront Hotel, Autograph Collection

9. Fairfield Inn & Suites By Marriott Annapolis

10. Hilton Garden Inn Annapolis Downtown

11. Laurel Grove Inn on the South

12. The Inn at Chesapeake Bay Beach Club

13. Microtel Inn & Suites by Wyndham Gambrills/Odenton

14. SpringHill Suites by Marriott Annapolis

15. TownePlace Suites by Marriott Annapolis

16. DoubleTree by Hilton Hotel Annapolis

17. Candlewood Suites Annapolis by IHG

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

19. Holiday Inn Express & Suites Annapolis by IHG

20. Hilton Garden Inn 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?