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

A living room with a fireplace, a chandelier, and a sofa.

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

Historic District, 2 km from Annapolis Sailing School

฿10,672

฿12,166 total

includes taxes & fees

6 Oct - 7 Oct

A white two-story building with a central entrance, a staircase, and a small garden area.

A table with a champagne bottle and glasses, a lamp, and a window with blinds.

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.

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

฿7,164

฿8,167 total

includes taxes & fees

4 Oct - 5 Oct

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

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.

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

3. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

฿7,635

฿8,704 total

includes taxes & fees

4 Oct - 5 Oct

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.

A historic brick building with a red roof, multiple windows, and a central staircase.

4. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Ashley

฿3,843

฿5,531 total

includes taxes & fees

25 Oct - 26 Oct

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

5. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

฿6,687

฿7,623 total

includes taxes & fees

25 Oct - 26 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.

A waterfront area with boats docked, a clear sky, and buildings in the background.

6. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

William

฿9,111

฿10,387 total

includes taxes & fees

12 Oct - 13 Oct

A modern lobby with a seating area, a fireplace, and a bookshelf.

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.

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

7. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

petra

฿4,381

฿4,995 total

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 spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

8. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

฿6,427

฿7,988 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 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.

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

9. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Mark

฿3,170

฿3,614 total

includes taxes & fees

12 Oct - 13 Oct

10. Laurel Grove Inn on the South

9.3 km from Annapolis Sailing School

Ruth

฿6,049

฿6,895 total

includes taxes & fees

4 Oct - 5 Oct

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 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.

11. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

฿3,021

฿3,444 total

includes taxes & fees

4 Oct - 5 Oct

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.

12. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Cynthia

฿3,696

฿4,214 total

includes taxes & fees

4 Oct - 5 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 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.

13. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

฿4,164

฿4,747 total

includes taxes & fees

28 Oct - 29 Oct

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.

14. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Darren

฿3,394

฿4,035 total

includes taxes & fees

26 Oct - 27 Oct

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

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

15. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Philip

฿3,056

฿3,484 total

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

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.

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.

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

7.4 km from Annapolis Sailing School

Leslie

฿3,199

฿3,647 total

includes taxes & fees

20 Oct - 21 Oct

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

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

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

17. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Jim

฿3,815

฿4,349 total

includes taxes & fees

6 Oct - 7 Oct

A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

A pool table with balls, a pool cue, and three framed pictures on the wall.

A hotel lobby with a dining area, a fireplace, and a view of the outside.

18. Hampton Inn & Suites Annapolis

6.4 km from Annapolis Sailing School

Courtney

฿3,530

฿4,024 total

includes taxes & fees

28 Oct - 29 Oct

A modern lobby with a reception desk, seating area, and potted plants.

A modern bar area with a wooden counter, bar stools, and a wine display.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

19. Hilton Garden Inn Annapolis

6.9 km from Annapolis Sailing School

Glenn

฿3,399

฿3,875 total

includes taxes & fees

12 Oct - 13 Oct

20. Village Inn Annapolis MD

6.3 km from Annapolis Sailing School

"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."

Keith

฿2,789

฿3,180 total

includes taxes & fees

1 Oct - 2 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
Flag House Inn	9.2 Wonderful 97 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,027 reviews	View
The Westin Annapolis	8.8 Excellent 1,000 reviews	View

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"V"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

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 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 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

Filter by

Star rating

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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. Flag House Inn

4. Historic Inns of Annapolis

5. The Westin Annapolis

6. Annapolis Waterfront Hotel, Autograph Collection

7. Hilton Garden Inn Annapolis Downtown

8. The Inn at Chesapeake Bay Beach Club

9. Microtel Inn & Suites by Wyndham Gambrills/Odenton

10. Laurel Grove Inn on the South

11. DoubleTree by Hilton Hotel Annapolis

12. Crowne Plaza Annapolis by IHG

13. TownePlace Suites by Marriott Annapolis

14. Candlewood Suites Annapolis by IHG

15. Sonesta ES Suites Annapolis

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

17. Courtyard by Marriott Annapolis

18. Hampton Inn & Suites Annapolis

19. Hilton Garden Inn Annapolis

20. Village Inn Annapolis MD

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

Inn at Horn Point

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