The Best Hotels Closest to Annapolis Sailing School in Annapolis for 2026

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

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

NT$9,356

NT$10,666 total

includes taxes & fees

Sep 27 - Sep 28

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

2. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

princess

NT$4,932

NT$5,623 total

includes taxes & fees

Sep 27 - Sep 28

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.

3. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

NT$7,208

NT$8,217 total

includes taxes & fees

Sep 27 - Sep 28

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

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

4. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

ian

NT$3,374

NT$4,931 total

includes taxes & fees

Oct 12 - Oct 13

An outdoor patio with tables, chairs, and a fire feature.

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.

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

5. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

NT$4,283

NT$4,883 total

includes taxes & fees

Sep 30 - Oct 1

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

2.7 km from Annapolis Sailing School

Bobbi

NT$5,678

NT$6,473 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

7. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

NT$6,068

NT$7,542 total

includes taxes & fees

Oct 19 - Oct 20

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

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.

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

8. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Arlaan

NT$2,939

NT$3,351 total

includes taxes & fees

Oct 12 - Oct 13

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

A swimming pool with a tiled edge, wooden chairs, and tables around it.

A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

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.

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

7.4 km from Annapolis Sailing School

Leslie

NT$3,020

NT$3,443 total

includes taxes & fees

Oct 20 - Oct 21

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

10. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

FRANK

NT$3,748

NT$4,273 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

11. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Cynthia

NT$3,489

NT$3,978 total

includes taxes & fees

Sep 27 - Sep 28

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.

12. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Stacy

NT$2,950

NT$3,520 total

includes taxes & fees

Oct 4 - Oct 5

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 compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

13. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

NT$3,743

NT$4,267 total

includes taxes & fees

Oct 4 - Oct 5

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

14. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Philip

NT$3,074

NT$3,504 total

includes taxes & fees

Sep 28 - Sep 29

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

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

A microwave, a coffee maker, and a refrigerator in a kitchen area.

A breakfast bar with labeled sections for cereal and fruit, a kettle, and condiments.

15. Holiday Inn Express & Suites Annapolis by IHG

6 km from Annapolis Sailing School

Wilma

NT$3,204

NT$3,652 total

includes taxes & fees

Sep 27 - Sep 28

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.

16. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Phyllis

NT$3,322

NT$3,787 total

includes taxes & fees

Sep 30 - Oct 1

17. 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

NT$2,633

NT$3,002 total

includes taxes & fees

Sep 27 - Sep 28

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 modern hotel kitchen with a buffet setup, including a waffle maker, coffee station, and various food containers.

A gym with treadmills, elliptical machines, a bench, and a rack of dumbbells.

18. Hampton Inn & Suites Annapolis

6.4 km from Annapolis Sailing School

Earnest

NT$3,184

NT$3,629 total

includes taxes & fees

Oct 4 - Oct 5

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

A Hilton Garden Inn with a large building and a smaller entrance building.

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

NT$3,096

NT$3,529 total

includes taxes & fees

Oct 12 - Oct 13

A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

A hotel room with a large bed, a desk with a laptop, a television, and a door with a curtain.

A gym with treadmills, elliptical machines, and exercise balls.

A hotel lobby with a reception desk, seating area, and dining space.

20. Best Western Annapolis

6.4 km from Annapolis Sailing School

Sanaul

NT$2,370

NT$2,702 total

includes taxes & fees

Sep 27 - Sep 28

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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
Graduate by Hilton Annapolis	9.4 Exceptional 1,005 reviews	View
Flag House Inn	9.2 Wonderful 97 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,011 reviews	View
Fairfield Inn & Suites By Marriott Annapolis	8.8 Excellent 239 reviews	View

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"I love the Graduate Hotel and it is very convenient. But please fix the parking garage gate 😬! It’s terrible!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

134 Prince - Luxury Boutique Hotel

10/10 Excellent

"Lovely hotel with incredible staff"

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 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.

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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, check out the 91 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 91 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.

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Maryland Vacation Rentals

Find hotels near Annapolis Sailing School, Annapolis from NT$2,702

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Treat yourself

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Our top choices for Annapolis Sailing School hotels

1. 86 State Circle - Luxury Boutique Hotel

2. Graduate by Hilton Annapolis

3. Flag House Inn

4. Historic Inns of Annapolis

5. Fairfield Inn & Suites By Marriott Annapolis

6. The Westin Annapolis

7. The Inn at Chesapeake Bay Beach Club

8. Microtel Inn & Suites by Wyndham Gambrills/Odenton

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

10. SpringHill Suites by Marriott Annapolis

11. Crowne Plaza Annapolis by IHG

12. Candlewood Suites Annapolis by IHG

13. TownePlace Suites by Marriott Annapolis

14. Sonesta ES Suites Annapolis

15. Holiday Inn Express & Suites Annapolis by IHG

16. Courtyard by Marriott Annapolis

17. Village Inn Annapolis MD

18. Hampton Inn & Suites Annapolis

19. Hilton Garden Inn Annapolis

20. Best Western Annapolis

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

134 Prince - Luxury Boutique Hotel

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

Explore a world of travel with Expedia