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

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

A bookshelf with books, decorative items, and a fireplace.

1. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

AED 1,096

AED 1,250 total

includes taxes & fees

27 Oct - 28 Oct

A brick building with a large window and a dome in the background.

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

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

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 970

AED 1,106 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

AED 509

AED 580 total

includes taxes & fees

22 Nov - 23 Nov

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

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

A dark blue bookshelf with decorative items and books.

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

AED 800

AED 912 total

includes taxes & fees

27 Oct - 28 Oct

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

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

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

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

AED 283

AED 449 total

includes taxes & fees

26 Nov - 27 Nov

A modern hotel room with a large bed, a flat-screen TV, a sofa, and a window with a view of greenery.

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

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

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

AED 496

AED 565 total

includes taxes & fees

1 Nov - 2 Nov

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

AED 466

AED 532 total

includes taxes & fees

1 Nov - 2 Nov

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

A store with shelves of beverages, a counter with a cash register, and baskets with items.

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

8. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

AED 621

AED 708 total

includes taxes & fees

22 Nov - 23 Nov

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

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

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

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

9. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

John

AED 790

AED 901 total

includes taxes & fees

8 Nov - 9 Nov

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

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

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Lori

AED 384

AED 438 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

AED 785

AED 965 total

includes taxes & fees

15 Nov - 16 Nov

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

A modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

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.

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Tucker

AED 315

AED 359 total

includes taxes & fees

23 Nov - 24 Nov

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

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.

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

13. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

AED 433

AED 494 total

includes taxes & fees

1 Nov - 2 Nov

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

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

14. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

AED 449

AED 620 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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.

15. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

FRANK

AED 403

AED 459 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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

7.4 km from Annapolis Sailing School

Catherine

AED 306

AED 348 total

includes taxes & fees

23 Nov - 24 Nov

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

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

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.

17. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

AED 334

AED 381 total

includes taxes & fees

26 Nov - 27 Nov

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

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

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

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

18. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

AED 364

AED 415 total

includes taxes & fees

24 Nov - 25 Nov

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

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

19. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Darren

AED 309

AED 370 total

includes taxes & fees

1 Nov - 2 Nov

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.

A gym with treadmills, weight machines, and dumbbells.

20. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Ann Christine

AED 312

AED 356 total

includes taxes & fees

16 Nov - 17 Nov

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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

Historic Inns of Annapolis

10/10 Excellent

"Great location!"

Eastport Cottage .5 mi from Downtown Annapolis

10/10 Excellent

"Cozy and comfortable cottage in a great location with easy accessibility to downtown Annapolis. The owner was excellent with communication. House had everything we needed for our stay. Especially appreciated good coffee, a decent hair dryer, and laundry. We all slept well, so the beds were comfortable too. Will definitely keep this one on our list for future Annapolis visits!"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Great place"

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."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Easy access to downtown, Great waterside restaurants."

Beautiful Condo - Water View Near City Dock

10/10 Excellent

"Lovely condo within walking distance of downtown Annapolis and many great restaurants in the neighborhood. The host was very responsive and helpful."

The Westin Annapolis

10/10 Excellent

"Great last minute booking. All went smoothly"

Eastport Historic Firehouse with Parking, Dogs OK

10/10 Excellent

"The Firehouse was comfortable, charming, well equipped, and clean. It is the perfect location to walk into town for the boat show and nearby restaurants. The hosts had good communication. We recommend this place for your Annapolis experience."

Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard

10/10 Excellent

"Excellent location. Perfect property. Very hard to rate price for value as a five because I was their during the sailboat show and all prices are (gulp) astronomical. I’m sure the pricing is better at other times. Overall, great stay. Perfect if you are visiting Eastport or downtown Annapolis."

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.

Find hotels near Annapolis Sailing School, Annapolis from AED 348

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Treat yourself

Be picky

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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

Historic Inns of Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

Hilton Garden Inn Annapolis Downtown

Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Beautiful Condo - Water View Near City Dock

The Westin Annapolis

Eastport Historic Firehouse with Parking, Dogs OK

Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard

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