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.

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

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

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

1. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

NT$8,780

NT$10,010 total

includes taxes & fees

Oct 28 - Oct 29

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 living room with a fireplace, a chandelier, and a sofa.

2. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Angela

NT$8,875

NT$10,117 total

includes taxes & fees

Oct 27 - Oct 28

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

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Nadine

NT$4,518

NT$5,150 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.

A dark blue bookshelf with decorative items and books.

A neatly made bed with white bedding, a striped pillow, and a vase with white flowers on a bedside table.

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

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Thomas

NT$7,103

NT$8,097 total

includes taxes & fees

Oct 27 - Oct 28

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.

A historic brick building with a red roof, multiple windows, and a central staircase.

5. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Christiaan

NT$2,793

NT$4,299 total

includes taxes & fees

Nov 9 - Nov 10

A laundry room with two wall-mounted washing machines, a bench, and two framed pictures on the wall.

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

A modern dining area with wooden tables and leather chairs, large windows with a view of greenery, and decorative wall mirrors.

A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

NT$4,401

NT$5,017 total

includes taxes & fees

Nov 1 - Nov 2

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

A bar area with a long counter, multiple stools, and a television above.

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

A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.

7. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

NT$4,140

NT$4,720 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

8. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

NT$5,510

NT$6,281 total

includes taxes & fees

Nov 22 - Nov 23

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 area with boats docked, a clear sky, and buildings in the background.

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

9. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

John

NT$7,016

NT$7,998 total

includes taxes & fees

Nov 8 - Nov 9

A hotel room with two beds, a desk with a chair, a television, and a large window with a view of greenery.

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Lori

NT$3,407

NT$3,884 total

includes taxes & fees

Nov 3 - Nov 4

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

A marina with multiple boats docked, a large building with a sign reading 'Wilson's Cove,' and a surrounding landscape with greenery and other buildings.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

A balcony with a view of a marina filled with boats.

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

NT$6,971

NT$8,567 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.

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

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

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

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Tucker

NT$2,799

NT$3,191 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.

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

A modern kitchen with a white countertop, stainless steel appliances, and wooden cabinets.

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$3,847

NT$4,385 total

includes taxes & fees

Nov 4 - Nov 5

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

A large, two-story white house with a porch and multiple windows.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

14. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

NT$3,989

NT$5,506 total

includes taxes & fees

Nov 17 - Nov 18

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

A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

A hotel pool area with two pools, chairs, and a sunshade.

A hotel reception area with a reception desk, a television, and seating area.

15. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

FRANK

NT$3,575

NT$4,075 total

includes taxes & fees

Nov 15 - Nov 16

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

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.

A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

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

7.4 km from Annapolis Sailing School

Catherine

NT$2,712

NT$3,092 total

includes taxes & fees

Nov 23 - Nov 24

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

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.

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

17. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

NT$2,967

NT$3,383 total

includes taxes & fees

Nov 22 - Nov 23

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

A modern lobby with a sectional sofa, a coffee table, and a blue armchair.

A hotel lobby with a bar area, seating arrangements, and a patterned carpet.

A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.

18. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

NT$3,228

NT$3,679 total

includes taxes & fees

Nov 24 - Nov 25

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

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

A hotel sign for Candlewood Suites with a modern building in the background.

An outdoor patio with a covered seating area, grill stations, and planters.

19. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Darren

NT$2,738

NT$3,283 total

includes taxes & fees

Nov 1 - Nov 2

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

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

20. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Ann Christine

NT$2,771

NT$3,159 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	9.8 Exceptional 49 reviews	View
86 State Circle - Luxury Boutique Hotel	9.8 Exceptional 11 reviews	View
Graduate by Hilton Annapolis	9.4 Exceptional 1,009 reviews	View
Flag House Inn	9.2 Wonderful 99 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,058 reviews	View

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Great location, friendly staff."

Historic Inns of Annapolis

10/10 Excellent

"Great location!"

Graduate by Hilton Annapolis

8/10 Good

"The hotel was clean and well located, and the staff was pleasant and helpful. My only complaint was that the mattress was a little soft, and I would have preferred a choice of pillows."

134 Prince - Luxury Boutique Hotel

8/10 Good

"A lovely property though not staffed full time. Some maintenance issues that were eventually resolved. Coffee and pastries available but not breakfast. Location was perfect for walking around town."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Easy access to downtown, Great waterside restaurants."

The Westin Annapolis

10/10 Excellent

"Great last minute booking. All went smoothly"

Flag House Inn

10/10 Excellent

"Great location in the heart of old Annapolis. Courtesy staff that were very friendly and helpful. A clean, relaxing room every day. Thank you!"

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 cityscape with a prominent clock tower, a marina with boats, and a mix of historic and modern buildings.

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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A coastal town with a marina, houses, and a bridge in the distance.

Spa Creek

Commune with nature and explore the great outdoors at Spa Creek during your travels in Annapolis.

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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.

See properties

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$3,092

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Treat yourself

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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. SpringHill 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

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Historic Inns of Annapolis

Graduate by Hilton Annapolis

134 Prince - Luxury Boutique Hotel

Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

Flag House Inn

Inn at Horn Point

Other attractions near Annapolis Sailing School

Susan Campbell Park

Ego Alley

Spa Creek

Annapolis Landing Marina

Annapolis Maritime Museum

Sparrows Beach

Annapolis Harbor

Carrs Beach

Frequently asked questions

Explore a world of travel with Expedia