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

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.

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 1.2 mi from Annapolis Sailing School

£230

includes taxes & fees

30 Sept - 1 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 table with a champagne bottle and glasses, a lamp, and a window with blinds.

A bookshelf with books, decorative items, and a fireplace.

2. 134 Prince - Luxury Boutique Hotel

1 mi from Annapolis Sailing School

Chris

£183

includes taxes & fees

30 Sept - 1 Oct

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

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

1.5 mi from Annapolis Sailing School

princess

£126

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 neatly made bed with white bedding, a striped pillow, and a vase with white flowers on a bedside table.

A dark blue bookshelf with decorative items and books.

A sailboat docked at a waterfront with buildings in the background.

4. Flag House Inn

Historic District, 1 mi from Annapolis Sailing School

Nathan

£187

includes taxes & fees

30 Sept - 1 Oct

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 District, 1.2 mi from Annapolis Sailing School

Ashley

£117

includes taxes & fees

12 Oct - 13 Oct

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 wooden tables and leather chairs, large windows with a view of greenery, and decorative wall mirrors.

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

6. Residence Inn By Marriott Annapolis

1.9 mi from Annapolis Sailing School

Francis

£131

includes taxes & fees

28 Oct - 29 Oct

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

1.8 mi from Annapolis Sailing School

Imola

£116

includes taxes & fees

28 Oct - 29 Oct

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

8. The Westin Annapolis

1.7 mi from Annapolis Sailing School

Bobbi

£171

includes taxes & fees

25 Oct - 26 Oct

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.

9. Hilton Garden Inn Annapolis Downtown

1.5 mi from Annapolis Sailing School

petra

£112

includes taxes & fees

25 Oct - 26 Oct

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

8.1 mi from Annapolis Sailing School

scott

£179

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 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.

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

12.2 mi from Annapolis Sailing School

Mark

£78

includes taxes & fees

12 Oct - 13 Oct

12. Laurel Grove Inn on the South

5.8 mi from Annapolis Sailing School

Ruth

£155

includes taxes & fees

29 Oct - 30 Oct

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 reception area with a reception desk, a television, and seating area.

13. SpringHill Suites by Marriott Annapolis

4 mi from Annapolis Sailing School

Lisa

£111

includes taxes & fees

26 Oct - 27 Oct

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.

14. TownePlace Suites by Marriott Annapolis

4.1 mi from Annapolis Sailing School

Nkusu Lauren

£102

includes taxes & fees

5 Oct - 6 Oct

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.

15. DoubleTree by Hilton Hotel Annapolis

3.9 mi from Annapolis Sailing School

Michele

£83

includes taxes & fees

1 Oct - 2 Oct

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

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

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.

16. Crowne Plaza Annapolis by IHG

3.9 mi from Annapolis Sailing School

Cynthia

£95

includes taxes & fees

4 Oct - 5 Oct

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.

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

An outdoor patio with a brick floor, surrounded by lush greenery and trees.

17. Candlewood Suites Annapolis by IHG

3.8 mi from Annapolis Sailing School

Darren

£84

includes taxes & fees

4 Oct - 5 Oct

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 Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

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

4.6 mi from Annapolis Sailing School

Leslie

£82

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A modern lobby with a reception desk, seating area, and a patterned rug.

A gym with treadmills, weight machines, and dumbbells.

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

19. Sonesta ES Suites Annapolis

4.1 mi from Annapolis Sailing School

Philip

£78

includes taxes & fees

28 Oct - 29 Oct

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

A hotel entrance with a covered walkway, a flag, and a landscaped area with trees.

A modern office setup with two monitors, a keyboard, and two wooden chairs.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

20. Holiday Inn Express & Suites Annapolis by IHG

3.7 mi from Annapolis Sailing School

Wilma

£90

includes taxes & fees

4 Oct - 5 Oct

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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 47 reviews	View
Graduate by Hilton Annapolis	9.4 Exceptional 1,012 reviews	View
Flag House Inn	9.2 Wonderful 97 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,026 reviews	View

Top Annapolis Sailing School Hotel Reviews

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!"

Eastport Cottage .5 mi from Downtown Annapolis

10/10 Excellent

"Terrific host, amazing location, lovely house."

Prime Eastport Location - Waterfront Condo w Pool & Parking

10/10 Excellent

"Amazing location with a stunning view!"

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."

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"

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."

Bay View Studio Apartment

10/10 Excellent

"Great spot for a couple beautiful location, convenient to downtown and a great peaceful view."

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

10/10 Excellent

"Awesome stay at this fantastic property."

Waterfront 2-Bedroom Condo on Spa Creek

10/10 Excellent

"Fabulous 17 days."

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 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 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 91 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 91 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. The Westin Annapolis

9. Hilton Garden Inn Annapolis Downtown

10. The Inn at Chesapeake Bay Beach Club

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

12. Laurel Grove Inn on the South

13. SpringHill Suites by Marriott Annapolis

14. TownePlace Suites by Marriott Annapolis

15. DoubleTree by Hilton Hotel Annapolis

16. Crowne Plaza Annapolis by IHG

17. Candlewood Suites Annapolis by IHG

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

19. Sonesta ES Suites Annapolis

20. Holiday Inn Express & Suites Annapolis by IHG

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

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

Eastport Cottage .5 mi from Downtown Annapolis

Prime Eastport Location - Waterfront Condo w Pool & Parking

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

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

Beautiful Condo - Water View Near City Dock

Bay View Studio Apartment

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Waterfront 2-Bedroom Condo on Spa Creek

Other attractions near Annapolis Sailing School

Susan Campbell Park

Ego Alley

Annapolis Landing Marina

Annapolis Maritime Museum

Sparrows Beach

Annapolis Harbor

Carrs Beach

Kunta Kinte Plaque & Alex Haley Memorial

Frequently asked questions