The Best Hotels Closest to Annapolis Sailing School in Annapolis - 2026 Updated Prices

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

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

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Rp5.282.544

Rp6.022.100 total

includes taxes & fees

18 Oct - 19 Oct

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.

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

Rp5.346.278

Rp6.094.757 total

includes taxes & fees

25 Oct - 26 Oct

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

2.3 km from Annapolis Sailing School

Mark

Rp2.629.270

Rp2.997.368 total

includes taxes & fees

26 Oct - 27 Oct

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.

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

Rp4.070.013

Rp4.639.825 total

includes taxes & fees

18 Oct - 19 Oct

A room with a fireplace, two armchairs, a table, and a chandelier.

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 spacious indoor area with brick walls, multiple tables and chairs, and string lights.

5. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Ashley

Rp1.533.672

Rp2.360.566 total

includes taxes & fees

9 Nov - 10 Nov

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 living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

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

Francis

Rp2.720.800

Rp3.101.712 total

includes taxes & fees

27 Oct - 28 Oct

A bar area with a long counter, multiple stools, and a television above.

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

Rp2.416.500

Rp2.754.810 total

includes taxes & fees

27 Oct - 28 Oct

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

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

8. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

William

Rp3.995.280

Rp4.554.619 total

includes taxes & fees

2 Nov - 3 Nov

9. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

petra

Rp1.893.225

Rp2.158.276 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

10. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

Rp4.009.288

Rp4.906.012 total

includes taxes & fees

19 Oct - 20 Oct

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 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.

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

paul

Rp1.598.735

Rp1.822.558 total

includes taxes & fees

3 Nov - 4 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 rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

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.

12. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

Rp2.168.061

Rp2.998.139 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

A hotel pool area with two pools, chairs, and a sunshade.

13. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Lisa

Rp2.131.647

Rp2.430.078 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

A modern kitchen with a white countertop, stainless steel appliances, and wooden cabinets.

14. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

Rp2.042.082

Rp2.327.974 total

includes taxes & fees

20 Oct - 21 Oct

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 hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

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

7.4 km from Annapolis Sailing School

Catherine

Rp1.633.666

Rp1.862.380 total

includes taxes & fees

9 Nov - 10 Nov

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 restaurant with wooden tables and chairs, a bar area, and a tiled floor.

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

16. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

Rp1.894.837

Rp2.160.114 total

includes taxes & fees

18 Oct - 19 Oct

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

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

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

17. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

Rp1.915.300

Rp2.183.442 total

includes taxes & fees

11 Nov - 12 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 room with a bed, desk, chair, television, and a window with curtains.

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

18. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Rp1.665.909

Rp1.987.626 total

includes taxes & fees

25 Oct - 26 Oct

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 patio area with a stone fire pit, outdoor furniture, and a covered seating area.

A gym with treadmills, weight machines, and dumbbells.

19. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Rp1.683.822

Rp1.919.557 total

includes taxes & fees

1 Nov - 2 Nov

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.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

20. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Jim

Rp1.797.032

Rp2.048.617 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
86 State Circle - Luxury Boutique Hotel	10.0 Exceptional 10 reviews	View
134 Prince - Luxury Boutique Hotel	9.8 Exceptional 48 reviews	View
Graduate by Hilton Annapolis	9.4 Exceptional 1,000 reviews	View
Flag House Inn	9.2 Wonderful 97 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,048 reviews	View

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

8/10 Good

"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"all good. Very good when it comes to parking during a boat show."

The Westin Annapolis

10/10 Excellent

"Easy parking. Super comfy bed."

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."

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 savour 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 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.

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, take a look at the 88 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 88 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, 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.

Search Hotels Near Annapolis Sailing School, Annapolis

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Annapolis Sailing School hotels

1. 86 State Circle - Luxury Boutique Hotel

2. 134 Prince - 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. Annapolis Waterfront Hotel, Autograph Collection

9. Hilton Garden Inn Annapolis Downtown

10. The Inn at Chesapeake Bay Beach Club

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

12. Kent Island Resort

13. SpringHill Suites by Marriott Annapolis

14. TownePlace Suites by Marriott Annapolis

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

16. DoubleTree by Hilton Hotel Annapolis

17. Crowne Plaza Annapolis by IHG

18. Candlewood Suites Annapolis by IHG

19. Sonesta ES Suites Annapolis

20. Courtyard by Marriott Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

Inn at Horn Point

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