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4 Oct - 5 Oct
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5 Oct - 6 Oct
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9 Oct - 11 Oct
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16 Oct - 18 Oct

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

1. 86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
Historic District, 2 km from Annapolis Sailing School
Norway
Jo
AED 1,062
AED 1,210 total
includes taxes & fees
6 Oct - 7 Oct
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 table with a champagne bottle and glasses, a lamp, and a window with blinds.

2. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
1.6 km from Annapolis Sailing School
United States
Chris
AED 1,253
AED 1,428 total
includes taxes & fees
20 Oct - 21 Oct
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 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 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.

3. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
2.3 km from Annapolis Sailing School
United States
Humberto
AED 539
AED 615 total
includes taxes & fees
26 Oct - 27 Oct
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 sailboat docked at a waterfront with buildings in the background.

4. Flag House Inn

Flag House Inn
Historic District, 1.7 km from Annapolis Sailing School
United States
Nathan
AED 800
AED 912 total
includes taxes & fees
5 Oct - 6 Oct
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.
An aerial view of a coastal town with a marina, houses, and a bridge in the background.
A marina with multiple boats docked during sunset.

5. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District, 1.9 km from Annapolis Sailing School
United States
Ashley
AED 314
AED 483 total
includes taxes & fees
1 Nov - 2 Nov
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 bar area with a long counter, multiple stools, and a television screen above.

6. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Francis
AED 558
AED 636 total
includes taxes & fees
27 Oct - 28 Oct
Residence Inn By Marriott Annapolis
An outdoor patio with tables, chairs, and a fire feature.
A modern living room with a fireplace, a sofa, and a coffee table.
A bar area with a long counter, multiple stools, and a television above.
A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

7. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Imola
AED 371
AED 423 total
includes taxes & fees
13 Oct - 14 Oct
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.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

8. The Westin Annapolis

The Westin Annapolis
2.7 km from Annapolis Sailing School
United States
Bobbi
AED 731
AED 833 total
includes taxes & fees
5 Oct - 6 Oct
The Westin Annapolis
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

Annapolis Waterfront Hotel, Autograph Collection
Historic District, 1.4 km from Annapolis Sailing School
United States
William
AED 849
AED 968 total
includes taxes & fees
1 Nov - 2 Nov
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 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
AED 419
AED 477 total
includes taxes & fees
1 Nov - 2 Nov
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 spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

11. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
13 km from Annapolis Sailing School
United States
scott
AED 702
AED 873 total
includes taxes & fees
19 Oct - 20 Oct
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 reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.
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.

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
AED 353
AED 402 total
includes taxes & fees
1 Nov - 2 Nov
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Land view from property
Interior detail
Floor plan
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
AED 661
AED 754 total
includes taxes & fees
6 Oct - 7 Oct
Laurel Grove Inn on the South
A large, two-story barn-style building with a covered front porch and a garage.
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.
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.

14. Kent Island Resort

Kent Island Resort
13.1 km from Annapolis Sailing School
United States
Bethany
AED 592
AED 782 total
includes taxes & fees
28 Oct - 29 Oct
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 room with a bed, a desk, a chair, a coffee machine, and a tray table.

15. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
6.4 km from Annapolis Sailing School
United States
Lisa
AED 474
AED 540 total
includes taxes & fees
25 Oct - 26 Oct
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 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.

16. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
6.7 km from Annapolis Sailing School
United States
Nkusu Lauren
AED 433
AED 494 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

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
AED 350
AED 399 total
includes taxes & fees
25 Oct - 26 Oct
Country Inn & Suites by Radisson, Annapolis, MD
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 DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

18. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
6.3 km from Annapolis Sailing School
United States
Michele
AED 356
AED 406 total
includes taxes & fees
12 Oct - 13 Oct
DoubleTree by Hilton Hotel Annapolis
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.

19. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
6.3 km from Annapolis Sailing School
United States
Cynthia
AED 419
AED 477 total
includes taxes & fees
3 Nov - 4 Nov
Crowne Plaza Annapolis by IHG
A modern living room with a large window, a dining area, and a kitchen in the background.
A hotel room with a bed, desk, chair, television, and a window with curtains.
An outdoor patio with a brick floor, surrounded by lush greenery and trees.
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
AED 342
AED 408 total
includes taxes & fees
1 Nov - 2 Nov
Candlewood Suites Annapolis by IHG
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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 13 hours ago
Graduate by Hilton Annapolis
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10/10 Excellent
"We had an absolutely incredible stay here over the Naval Academy reunion weekend! The house was the perfect home base for all the festivities. The absolute highlight was the pool area—it was the ultimate spot for hosting classmates, catching up, and relaxing between reunion events. Plus, the location was incredibly convenient; being able to easily hop on the water taxi made getting downtown and back completely seamless. The layout of the home accommodated everyone comfortably, the amenities were fantastic, and the host was incredibly welcoming and communicative. If you’re coming to Annapolis for a Navy weekend, this is the place to stay. Go Navy! Beat Army!"
Dawn Heather G. 3-night trip
Posted 9 days ago
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Eastport Cottage .5 mi from Downtown Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

10/10 Excellent
"Terrific host, amazing location, lovely house."
Carla M. 2-night trip
Posted 12 days ago
Eastport Cottage .5 mi from Downtown Annapolis
Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

10/10 Excellent
"House was pristine. Very comfortable space for a group. Great location. Very walkable."
Colleen E. 3-night trip
Posted 13 days ago
Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Waterfront 2-Bedroom Condo on Spa Creek

Waterfront 2-Bedroom Condo on Spa Creek

10/10 Excellent
"Beautiful condo in an incredible location. It was very easy to walk to downtown as well as local restaurants and a bakery for breakfast. I did not realize the second bedroom is a pull-out sofa only (my error for not digging into the website particulars). Marie was very understanding, however, there were not any other accommodations available. I can not speak enough about the beauty of the location and the peaceful atmosphere."
Shannon V. 2-night trip
Posted 2 weeks ago
Waterfront 2-Bedroom Condo on Spa Creek
Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard

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

10/10 Excellent
"Very clean and comfortable beds. Good amenities as well. Would suggest larger towels and a couple of boxes of tissues"
janice l. 2-night trip
Posted 3 weeks ago
Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard
Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock

10/10 Excellent
"Perfect location, easy walking to everything in downtown, and plenty of parking. Condo was small but very nice. Host was very responsive and checked in on us."
James P. 5-night trip
Posted 3 weeks ago
Beautiful Condo - Water View Near City Dock
Bay View Studio Apartment

Bay View Studio Apartment

10/10 Excellent
"Great spot for a couple beautiful location, convenient to downtown and a great peaceful view."
Rodney M. 2-night trip
Posted 3 weeks ago
Bay View Studio Apartment
Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

10/10 Excellent
"Was just perfect!! Stayed there twice this summer! Loved being there! So clean and has everything you need."
Lizzy H. 17-night trip
Posted 2 months ago
Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

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.
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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 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.