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

A bedroom with a large window, a chair, a bedside table with a lamp, and a bookshelf.

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

A cozy lounge area with a cushioned bench, two small tables with lamps, a brick wall, and a fireplace.

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

NT$10,093

NT$11,506 total

includes taxes & fees

Oct 6 - Oct 7

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

A dining room with a large rectangular table, six chairs, a chandelier, and a built-in bookshelf with various decorative items.

A table with a champagne bottle and glasses, a lamp, and a window with blinds.

A couple standing in front of a black wooden building with white-framed windows.

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

NT$6,775

NT$7,723 total

includes taxes & fees

Oct 4 - Oct 5

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

A sailboat docked at a waterfront with buildings in the background.

A dark blue bookshelf with decorative items and books.

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

3. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

NT$7,221

NT$8,232 total

includes taxes & fees

Oct 4 - Oct 5

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

A marina with multiple boats docked during sunset.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

4. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Ashley

NT$3,379

NT$4,939 total

includes taxes & fees

Oct 12 - Oct 13

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

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

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

5. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

NT$6,324

NT$7,210 total

includes taxes & fees

Oct 25 - Oct 26

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

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

6. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

William

NT$8,617

NT$9,824 total

includes taxes & fees

Oct 25 - Oct 26

A modern lobby with a seating area, a fireplace, and a bookshelf.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

7. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

petra

NT$4,064

NT$4,633 total

includes taxes & fees

Oct 1 - Oct 2

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

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

8. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

NT$6,078

NT$7,555 total

includes taxes & fees

Oct 19 - Oct 20

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

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

A snack and beverage vending area with various snacks and drinks.

9. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Mark

NT$2,998

NT$3,418 total

includes taxes & fees

Oct 12 - Oct 13

10. Laurel Grove Inn on the South

9.3 km from Annapolis Sailing School

Ruth

NT$5,720

NT$6,521 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

11. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

NT$2,857

NT$3,257 total

includes taxes & fees

Oct 4 - Oct 5

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A multi-story hotel with a brick facade, large windows, and an American flag.

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

12. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Cynthia

NT$3,496

NT$3,985 total

includes taxes & fees

Oct 4 - Oct 5

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

A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

13. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

NT$3,750

NT$4,275 total

includes taxes & fees

Oct 5 - Oct 6

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

A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

A hotel room with a bed, desk, chair, television, and a window with curtains.

A modern gym with weight racks, benches, and exercise equipment.

14. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Darren

NT$3,210

NT$3,816 total

includes taxes & fees

Oct 26 - Oct 27

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

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

A modern lobby with a reception desk, seating area, and a patterned rug.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

15. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Philip

NT$2,892

NT$3,297 total

includes taxes & fees

Oct 28 - Oct 29

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

A swimming pool with a tiled edge, wooden chairs, and tables around it.

A hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

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

7.4 km from Annapolis Sailing School

Leslie

NT$3,025

NT$3,449 total

includes taxes & fees

Oct 20 - Oct 21

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

A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

17. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Jim

NT$3,608

NT$4,113 total

includes taxes & fees

Oct 5 - Oct 6

A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

A hotel lobby with a dining area, a fireplace, and a view of the outside.

A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

A pool table with balls, a pool cue, and three framed pictures on the wall.

18. Hampton Inn & Suites Annapolis

6.4 km from Annapolis Sailing School

Courtney

NT$3,338

NT$3,806 total

includes taxes & fees

Oct 28 - Oct 29

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

A Hilton Garden Inn with a large building and a smaller entrance building.

A modern bar area with a wooden counter, bar stools, and a wine display.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

19. Hilton Garden Inn Annapolis

6.9 km from Annapolis Sailing School

Glenn

NT$3,101

NT$3,535 total

includes taxes & fees

Oct 12 - Oct 13

20. Village Inn Annapolis MD

6.3 km from Annapolis Sailing School

"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."

Keith

NT$2,638

NT$3,007 total

includes taxes & fees

Oct 1 - Oct 2

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Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
86 State Circle - Luxury Boutique Hotel	10.0 Exceptional 10 reviews	View
134 Prince - Luxury Boutique Hotel	9.8 Exceptional 47 reviews	View
Flag House Inn	9.2 Wonderful 97 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,027 reviews	View
The Westin Annapolis	8.8 Excellent 1,000 reviews	View

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"V"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

134 Prince - Luxury Boutique Hotel

10/10 Excellent

"Lovely hotel with incredible staff"

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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A waterfront dining area with boats docked nearby.

Ego Alley

Explore the waterfront in Annapolis with a trip to Ego Alley. While you're here, you can savor the top-notch restaurants.

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Annapolis Landing Marina

Explore the waterfront in Annapolis with a trip to Annapolis Landing Marina. Stroll along the riverfront or experience the area's live music.

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Annapolis Maritime Museum

9.0/10 (27 reviews)

You can study the exhibits at Annapolis Maritime Museum, a museum with a storied past, during your trip to Annapolis. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

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Sparrows Beach

Why not spend a lazy afternoon at Sparrows Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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Annapolis Harbor

Explore the waterfront in Annapolis with a trip to Annapolis Harbor.

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Carrs Beach

Why not spend a lazy afternoon at Carrs Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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Kunta Kinte Plaque & Alex Haley Memorial

You can find out about the history of Annapolis with a visit to Kunta Kinte Plaque & Alex Haley Memorial.

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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 91 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 91 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$3,007

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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. Flag House Inn

4. Historic Inns of Annapolis

5. The Westin Annapolis

6. Annapolis Waterfront Hotel, Autograph Collection

7. Hilton Garden Inn Annapolis Downtown

8. The Inn at Chesapeake Bay Beach Club

9. Microtel Inn & Suites by Wyndham Gambrills/Odenton

10. Laurel Grove Inn on the South

11. DoubleTree by Hilton Hotel Annapolis

12. Crowne Plaza Annapolis by IHG

13. TownePlace Suites by Marriott Annapolis

14. Candlewood Suites Annapolis by IHG

15. Sonesta ES Suites Annapolis

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

17. Courtyard by Marriott Annapolis

18. Hampton Inn & Suites Annapolis

19. Hilton Garden Inn Annapolis

20. Village Inn Annapolis MD

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

134 Prince - Luxury Boutique Hotel

Inn at Horn Point

Other attractions near Annapolis Sailing School

Susan Campbell Park

Ego Alley

Annapolis Landing Marina

Annapolis Maritime Museum

Sparrows Beach

Annapolis Harbor

Carrs Beach

Kunta Kinte Plaque & Alex Haley Memorial

Frequently asked questions

Explore a world of travel with Expedia