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

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, 2 km from Annapolis Sailing School

₹26,413

₹30,111 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 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

1.6 km from Annapolis Sailing School

Chris

₹28,587

₹32,589 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 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.

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.

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Mark

₹14,059

₹16,027 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 sailboat docked at a waterfront with buildings in the background.

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

₹21,649

₹24,680 total

includes taxes & fees

18 Oct - 19 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.

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

₹8,164

₹12,565 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

₹14,483

₹16,511 total

includes taxes & fees

27 Oct - 28 Oct

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.

7. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Imola

₹12,863

₹14,664 total

includes taxes & fees

27 Oct - 28 Oct

A balcony with a table set for two, overlooking a marina with boats.

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.

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

Historic District, 1.4 km from Annapolis Sailing School

William

₹21,267

₹24,244 total

includes taxes & fees

2 Nov - 3 Nov

9. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

petra

₹10,079

₹11,490 total

includes taxes & fees

10 Nov - 11 Nov

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

10. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

₹19,438

₹24,000 total

includes taxes & fees

2 Nov - 3 Nov

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

19.7 km from Annapolis Sailing School

paul

₹8,549

₹9,745 total

includes taxes & fees

3 Nov - 4 Nov

A large, two-story barn-style building with a covered front porch and a garage.

A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

A large, two-story white house with a porch and multiple windows.

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

₹11,532

₹15,948 total

includes taxes & fees

28 Oct - 29 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 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.

13. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Lisa

₹11,339

₹12,926 total

includes taxes & fees

9 Nov - 10 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 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.

14. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

₹10,862

₹12,383 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 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.

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

7.4 km from Annapolis Sailing School

₹8,690

₹9,906 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 modern living room with a sofa, armchairs, a coffee table, and a fireplace.

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

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

16. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

₹10,132

₹11,550 total

includes taxes & fees

18 Oct - 19 Oct

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

17. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

₹10,195

₹11,623 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.

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

A hotel room with a bed, desk, chair, television, and a window with curtains.

18. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Darren

₹8,861

₹10,573 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 modern lobby with a reception desk, seating area, and a patterned rug.

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

Dennis

₹9,052

₹10,319 total

includes taxes & fees

8 Nov - 9 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.

20. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Jim

₹9,609

₹10,954 total

includes taxes & fees

1 Nov - 2 Nov

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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 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

Historic Inns of Annapolis

10/10 Excellent

"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."

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

Historic Inns of Annapolis

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