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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 cozy lounge area with a cushioned bench, two small tables with lamps, a brick wall, and a fireplace.
A living room with a fireplace, a chandelier, and a sofa.
A church with a spire, surrounded by trees and illuminated by warm lights.

1. 86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
Historic District, 2 km from Annapolis Sailing School
Norway
Jo
NT$8,644
NT$9,854 total
includes taxes & fees
Sep 23 - Sep 24
86 State Circle - 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 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.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
2.3 km from Annapolis Sailing School
United States
Boryana
NT$4,862
NT$5,543 total
includes taxes & fees
Sep 30 - Oct 1
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 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 dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.

3. Flag House Inn

Flag House Inn
Historic District, 1.7 km from Annapolis Sailing School
United States
Nathan
NT$6,918
NT$7,886 total
includes taxes & fees
Sep 23 - Sep 24
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.

4. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District, 1.9 km from Annapolis Sailing School
United States
Shennetta
NT$3,134
NT$4,659 total
includes taxes & fees
Oct 12 - Oct 13
Historic Inns of Annapolis
An outdoor patio with tables, chairs, and a fire feature.
A bar area with a long counter, multiple stools, and a television screen above.
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.

5. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Francis
NT$4,572
NT$5,212 total
includes taxes & fees
Sep 30 - Oct 1
Residence Inn By Marriott Annapolis
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 lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

6. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Imola
NT$4,287
NT$4,887 total
includes taxes & fees
Sep 30 - Oct 1
Fairfield Inn & Suites By Marriott Annapolis
A balcony with a table set for two, overlooking a marina with boats.
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.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.

7. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District, 1.4 km from Annapolis Sailing School
United States
William
NT$7,341
NT$8,369 total
includes taxes & fees
Oct 4 - Oct 5
Annapolis Waterfront Hotel, Autograph Collection
A modern lobby with a seating area, a fireplace, and a bookshelf.
A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.
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.

8. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
2.5 km from Annapolis Sailing School
United States
Jeffrey
NT$3,879
NT$4,423 total
includes taxes & fees
Sep 30 - Oct 1
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 living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

9. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
13 km from Annapolis Sailing School
United States
scott
NT$6,073
NT$7,548 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 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.

10. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton
19.7 km from Annapolis Sailing School
United States
Arlaan
NT$2,915
NT$3,323 total
includes taxes & fees
Oct 12 - Oct 13
Microtel Inn & Suites by Wyndham Gambrills/Odenton
A large, two-story barn-style building with a covered front porch and a garage.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A large, two-story white house with a porch and multiple windows.

11. Kent Island Resort

Kent Island Resort
13.1 km from Annapolis Sailing School
United States
Bethany
NT$4,861
NT$6,470 total
includes taxes & fees
Oct 12 - Oct 13
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 reception area with a reception desk, a television, and seating area.
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

12. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
6.4 km from Annapolis Sailing School
United States
FRANK
NT$4,096
NT$4,669 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill 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 Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.
A swimming pool with a tiled edge, wooden chairs, and tables around it.

13. 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$3,023
NT$3,446 total
includes taxes & fees
Oct 12 - Oct 13
Country Inn & Suites by Radisson, Annapolis, MD
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
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.

14. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
6.3 km from Annapolis Sailing School
United States
Cynthia
NT$3,493
NT$3,982 total
includes taxes & fees
Sep 30 - Oct 1
Crowne Plaza Annapolis by IHG
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
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.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

15. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
6.3 km from Annapolis Sailing School
United States
Michele
NT$2,634
NT$3,002 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton Hotel Annapolis
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 modern gym with weight racks, benches, and exercise equipment.
A hotel room with a bed, desk, chair, television, and a window with curtains.

16. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
6.2 km from Annapolis Sailing School
United States
Stacy
NT$3,119
NT$3,713 total
includes taxes & fees
Oct 4 - Oct 5
Candlewood Suites Annapolis by IHG
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.

17. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
6.6 km from Annapolis Sailing School
United States
Philip
NT$3,077
NT$3,507 total
includes taxes & fees
Oct 1 - Oct 2
Sonesta ES Suites Annapolis

18. Laurel Grove Inn on the South

Laurel Grove Inn on the South
9.3 km from Annapolis Sailing School
United States
Ruth
NT$5,715
NT$6,516 total
includes taxes & fees
Oct 4 - Oct 5
Laurel Grove Inn on the South
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

19. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
6.8 km from Annapolis Sailing School
United States
Phyllis
NT$3,185
NT$3,631 total
includes taxes & fees
Sep 28 - Sep 29
Courtyard by Marriott Annapolis
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.
A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.
A microwave, a coffee maker, and a refrigerator in a kitchen area.
A breakfast bar with labeled sections for cereal and fruit, a kettle, and condiments.

20. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
6 km from Annapolis Sailing School
United States
Wilma
NT$3,214
NT$3,664 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express & 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 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
1,002 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
2,018 reviews
View
An outdoor patio with tables, chairs, and a fire feature.
Residence Inn By Marriott Annapolis
9.0
Wonderful
91 reviews
View

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"The restaurant inside the hotel is a great idea. but the variety of food is very limited. But it is just my opinion."
Paul and Maryse 3-night trip
Posted less than an hour ago
Hilton Garden Inn Annapolis Downtown
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."
Karen 3-night trip
Posted 3 hours ago
Annapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 19 hours 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 8 days 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 3 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.
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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.
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 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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