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Check prices for these dates

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23 Aug - 24 Aug
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24 Aug - 25 Aug
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28 Aug - 30 Aug
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4 Sep - 6 Sep

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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 bookshelf with books, decorative items, and a fireplace.
A couple standing in front of a black wooden building with white-framed windows.

1. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
1.6 km from Annapolis Sailing School
United States
Chris
฿8,799
฿10,031 total
includes taxes & fees
25 Aug - 26 Aug
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 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.

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
2.3 km from Annapolis Sailing School
United States
Patricia
฿4,859
฿5,539 total
includes taxes & fees
30 Aug - 31 Aug
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 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.
A dark blue bookshelf with decorative items and books.

3. Flag House Inn

Flag House Inn
Historic District, 1.7 km from Annapolis Sailing School
United States
Nathan
฿7,118
฿8,114 total
includes taxes & fees
24 Aug - 25 Aug
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 marina with multiple boats docked during sunset.
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.

4. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District, 1.9 km from Annapolis Sailing School
United States
Stephanie
฿3,022
฿4,562 total
includes taxes & fees
30 Aug - 31 Aug
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.

5. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Caitlin
฿4,704
฿5,363 total
includes taxes & fees
30 Aug - 31 Aug
Residence Inn 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.

6. The Westin Annapolis

The Westin Annapolis
2.7 km from Annapolis Sailing School
United States
susan greco
฿5,521
฿6,294 total
includes taxes & fees
30 Aug - 31 Aug
The Westin 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 bar area with a long counter, multiple stools, and a television above.

7. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3 km from Annapolis Sailing School
United States
Gary
฿4,149
฿4,730 total
includes taxes & fees
27 Aug - 28 Aug
Fairfield Inn & Suites By Marriott Annapolis
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 hotel room with a large bed, a chair, a small table, and a view of a body of water.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

8. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District, 1.4 km from Annapolis Sailing School
United States
Deanna
฿6,769
฿7,717 total
includes taxes & fees
30 Aug - 31 Aug
Annapolis Waterfront Hotel, Autograph Collection
A modern lobby with a seating area, a fireplace, and a bookshelf.
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.
A restaurant with a yellow cushioned bench, wooden tables, and chairs.

9. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
2.5 km from Annapolis Sailing School
United States
Nelson
฿3,456
฿3,940 total
includes taxes & fees
7 Sept - 8 Sept
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 residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

10. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
13 km from Annapolis Sailing School
United Kingdom
Jamie
฿7,045
฿8,651 total
includes taxes & fees
31 Aug - 1 Sept
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 reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.
A snack and beverage vending area with various snacks and drinks.

11. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
19.7 km from Annapolis Sailing School
United States
James
฿2,999
฿3,419 total
includes taxes & fees
30 Aug - 31 Aug
Microtel Inn & Suites by Wyndham Gambrills
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 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.

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

Country Inn & Suites by Radisson, Annapolis, MD
7.4 km from Annapolis Sailing School
United States
Leslie
฿3,110
฿3,546 total
includes taxes & fees
13 Sept - 14 Sept
Country Inn & Suites by Radisson, Annapolis, MD
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.

13. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
6.4 km from Annapolis Sailing School
United States
Joshua
฿4,214
฿4,804 total
includes taxes & fees
24 Aug - 25 Aug
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 hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.
A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.
A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

14. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
6.7 km from Annapolis Sailing School
United States
Jamila
฿3,855
฿4,395 total
includes taxes & fees
30 Aug - 31 Aug
TownePlace Suites by Marriott Annapolis
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a high ceiling with skylights.
A hotel lobby with a bar area, seating, and a patterned carpet.
A multi-story hotel with a brick facade, large windows, and an American flag.
A modern lobby with a central seating area, a chandelier, and a bookshelf.

15. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
6.3 km from Annapolis Sailing School
United States
Heather
฿3,430
฿3,911 total
includes taxes & fees
7 Sept - 8 Sept
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.

16. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
6.3 km from Annapolis Sailing School
United States
Fabiana
฿3,188
฿3,634 total
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hotel Annapolis
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 greenery and trees.
A modern gym with weight racks, benches, and exercise equipment.
A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

17. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
6.2 km from Annapolis Sailing School
United States
Javier
฿3,202
฿3,811 total
includes taxes & fees
30 Aug - 31 Aug
Candlewood Suites Annapolis by IHG
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A gym with treadmills, weight machines, and dumbbells.
A modern lobby with a reception desk, seating area, and a patterned rug.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

18. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
6.6 km from Annapolis Sailing School
United States
John
฿3,267
฿3,724 total
includes taxes & fees
22 Sept - 23 Sept
Sonesta ES Suites Annapolis
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.
A laundry room with four stacked washing machines and a black shelf.
A hotel reception desk with a modern design, a digital screen, and a beverage refrigerator.
A buffet with labeled food stations including omelets and cheese.

19. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
6 km from Annapolis Sailing School
United States
Frank
฿3,430
฿3,911 total
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn Express & Suites Annapolis by IHG
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 modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

20. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
6.8 km from Annapolis Sailing School
United States
Phyllis
฿3,006
฿3,426 total
includes taxes & fees
30 Aug - 31 Aug
Courtyard by Marriott Annapolis
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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 white two-story building with a central entrance, a staircase, and a small garden area.
134 Prince - Luxury Boutique Hotel
9.8
Exceptional
46 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
1,027 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
1,970 reviews
View
An outdoor patio with tables, chairs, and a fire feature.
Residence Inn By Marriott Annapolis
9.0
Wonderful
85 reviews
View

Top Annapolis Sailing School Hotel Reviews

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 2 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 savour 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 travels to Annapolis. Stroll along the area's waterfront or simply savour 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 when you stop by Kunta Kinte Plaque & Alex Haley Memorial.
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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, take a look at the 93 hotels and other accommodation options you'll find within a mile.
What's the best place to stay near Annapolis Sailing School?
Annapolis Waterfront Hotel, Autograph Collection is one of the top choices for your stay based on our traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. 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 will I be able to find near Annapolis Sailing School?
Expedia has 93 hotels and other accommodation options 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, you'll find most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review the best options available near Annapolis Sailing School.
What can I see and do near Annapolis Sailing School?
Study the collections at Annapolis Maritime Museum, London Town or Hammond-Harwood House. Explore landmarks like William Paca House, Kunta Kinte Plaque & Alex Haley Memorial and Maynard-Burgess House. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.