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

1. 86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
Historic District, 2 km from Annapolis Sailing School
Norway
Jo
NT$9,396
NT$10,711 total
includes taxes & fees
Oct 6 - Oct 7
86 State Circle - Luxury Boutique Hotel
A white two-story building with a central entrance, a staircase, and a small garden area.
A bookshelf with books, decorative items, and a fireplace.
A couple standing in front of a black wooden building with white-framed windows.
A dining room with a large rectangular table, six chairs, a chandelier, and a built-in bookshelf with various decorative items.

2. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
1.6 km from Annapolis Sailing School
United States
Chris
NT$10,868
NT$12,389 total
includes taxes & fees
Oct 20 - Oct 21
134 Prince - Luxury Boutique Hotel
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 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.
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.

3. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
2.3 km from Annapolis Sailing School
United States
Humberto
NT$4,677
NT$5,331 total
includes taxes & fees
Oct 26 - Oct 27
Graduate by Hilton Annapolis
A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.
A dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.
A sailboat docked at a waterfront with buildings in the background.
A neatly made bed with white bedding, a striped pillow, and a vase with white flowers on a bedside table.

4. Flag House Inn

Flag House Inn
Historic District, 1.7 km from Annapolis Sailing School
United States
Nathan
NT$6,942
NT$7,913 total
includes taxes & fees
Oct 5 - Oct 6
Flag House Inn
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
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.
An aerial view of a coastal town with a marina, houses, and a bridge in the background.

5. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District, 1.9 km from Annapolis Sailing School
United States
Ashley
NT$2,722
NT$4,192 total
includes taxes & fees
Nov 1 - Nov 2
Historic Inns of Annapolis
An outdoor patio with tables, chairs, and a fire feature.
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.
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

Residence Inn By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Francis
NT$4,843
NT$5,521 total
includes taxes & fees
Oct 27 - Oct 28
Residence Inn By Marriott Annapolis
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.
A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.
A modern living room with a fireplace, a sofa, and a coffee table.

7. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Imola
NT$3,218
NT$3,668 total
includes taxes & fees
Oct 13 - Oct 14
Fairfield Inn & Suites By Marriott Annapolis
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.
View from property
A store with shelves of beverages, a counter with a cash register, and baskets with items.

8. The Westin Annapolis

The Westin Annapolis
2.7 km from Annapolis Sailing School
United States
Bobbi
NT$6,340
NT$7,228 total
includes taxes & fees
Oct 5 - Oct 6
The Westin Annapolis
A balcony with a table set for two, overlooking a marina with boats.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.
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

Annapolis Waterfront Hotel, Autograph Collection
Historic District, 1.4 km from Annapolis Sailing School
United States
William
NT$7,366
NT$8,398 total
includes taxes & fees
Nov 1 - Nov 2
Annapolis Waterfront Hotel, Autograph Collection
A modern lobby with a seating area, a fireplace, and a bookshelf.
A restaurant with a yellow cushioned bench, wooden tables, and chairs.
A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.
A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

10. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
2.5 km from Annapolis Sailing School
United Kingdom
petra
NT$3,632
NT$4,140 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Annapolis Downtown
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 spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

11. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
13 km from Annapolis Sailing School
United States
scott
NT$6,093
NT$7,574 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.
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.
A modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton
19.7 km from Annapolis Sailing School
United States
Mark
NT$3,060
NT$3,489 total
includes taxes & fees
Nov 1 - Nov 2
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Land view from property
Outdoor dining
Interior detail
Interior detail

13. Laurel Grove Inn on the South

Laurel Grove Inn on the South
9.3 km from Annapolis Sailing School
United States
Ruth
NT$5,735
NT$6,538 total
includes taxes & fees
Oct 6 - Oct 7
Laurel Grove Inn on the South
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

Kent Island Resort
13.1 km from Annapolis Sailing School
United States
Bethany
NT$5,133
NT$6,782 total
includes taxes & fees
Oct 28 - Oct 29
Kent Island Resort
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 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

SpringHill Suites by Marriott Annapolis
6.4 km from Annapolis Sailing School
United States
Lisa
NT$4,110
NT$4,685 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Annapolis
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 hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.
A modern kitchen with a white countertop, stainless steel appliances, and wooden cabinets.

16. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
6.7 km from Annapolis Sailing School
United States
Nkusu Lauren
NT$3,760
NT$4,286 total
includes taxes & fees
Nov 1 - Nov 2
TownePlace Suites by Marriott Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.
A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

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

Country Inn & Suites by Radisson, Annapolis, MD
7.4 km from Annapolis Sailing School
United States
Leslie
NT$3,033
NT$3,458 total
includes taxes & fees
Oct 25 - Oct 26
Country Inn & Suites by Radisson, Annapolis, MD
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 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.

18. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
6.3 km from Annapolis Sailing School
United States
Michele
NT$3,087
NT$3,519 total
includes taxes & fees
Oct 12 - Oct 13
DoubleTree by Hilton Hotel Annapolis
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 modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

19. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
6.3 km from Annapolis Sailing School
United States
Cynthia
NT$3,632
NT$4,141 total
includes taxes & fees
Nov 3 - Nov 4
Crowne Plaza Annapolis by IHG
A modern living room with a large window, a dining area, and a kitchen in the background.
An outdoor patio with a brick floor, surrounded by lush greenery and trees.
A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.
A modern gym with weight racks, benches, and exercise equipment.

20. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
6.2 km from Annapolis Sailing School
United States
Darren
NT$2,963
NT$3,535 total
includes taxes & fees
Nov 1 - Nov 2
Candlewood Suites Annapolis by IHG
View all properties

Compare popular hotels close to Annapolis Sailing School

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.
86 State Circle - Luxury Boutique Hotel
10.0
Exceptional
10 reviews
View
A white two-story building with a central entrance, a staircase, and a small garden area.
134 Prince - Luxury Boutique Hotel
9.8
Exceptional
47 reviews
View
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
Graduate by Hilton Annapolis
9.4
Exceptional
1,001 reviews
View
A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.
Flag House Inn
9.2
Wonderful
97 reviews
View
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
Historic Inns of Annapolis
9.0
Wonderful
2,027 reviews
View

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great Hotel in a very central location"
Mark 2-night trip
Posted 7 hours ago
Graduate by Hilton Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 12 days ago
The Westin Annapolis
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

10/10 Excellent
"Lovely hotel with incredible staff"
Jason 3-night trip
Posted 3 weeks ago
134 Prince - Luxury Boutique Hotel
Inn at Horn Point

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."
Allison J 2-night trip
Posted 4 months ago
Inn at Horn Point

Other attractions near Annapolis Sailing School

A marina with boats docked, wooden pilings, and a clear sky.
Photo by Michael Lore

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
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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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.
See properties

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.
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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