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 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.

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

Angela

AED 960

AED 1,094 total

includes taxes & fees

21 Oct - 22 Oct

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

A couple standing in front of a black wooden building with white-framed windows.

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.

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

AED 1,096

AED 1,250 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 bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

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

2.3 km from Annapolis Sailing School

Nadine

AED 569

AED 649 total

includes taxes & fees

11 Nov - 12 Nov

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

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

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Thomas

AED 835

AED 951 total

includes taxes & fees

26 Oct - 27 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 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, 1.9 km from Annapolis Sailing School

Jennifer

AED 315

AED 484 total

includes taxes & fees

30 Oct - 31 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 modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Francis

AED 558

AED 636 total

includes taxes & fees

27 Oct - 28 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

3 km from Annapolis Sailing School

Imola

AED 496

AED 565 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

AED 820

AED 935 total

includes taxes & fees

1 Nov - 2 Nov

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.

9. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

AED 731

AED 833 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with two beds, a desk with a television, a chair, and a balcony with a view of the city.

A conference room with multiple round tables and chairs, large windows with curtains, and a patterned carpet.

A multi-story hotel with a modern design, featuring a prominent entrance with arches and a sign for Hilton Garden Inn.

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

petra

AED 389

AED 443 total

includes taxes & fees

2 Nov - 3 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 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.

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

AED 785

AED 965 total

includes taxes & fees

15 Nov - 16 Nov

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.

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Tucker

AED 328

AED 374 total

includes taxes & fees

15 Nov - 16 Nov

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

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

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.

13. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

AED 449

AED 620 total

includes taxes & fees

11 Nov - 12 Nov

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 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.

14. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Kaiya

AED 437

AED 498 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 hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

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

15. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

AED 433

AED 494 total

includes taxes & fees

1 Nov - 2 Nov

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

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

16. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

AED 389

AED 444 total

includes taxes & fees

17 Nov - 18 Nov

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

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.

A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

17. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

AED 358

AED 409 total

includes taxes & fees

27 Oct - 28 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 hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

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

18. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Darren

AED 309

AED 370 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

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

7.4 km from Annapolis Sailing School

Catherine

AED 335

AED 382 total

includes taxes & fees

9 Nov - 10 Nov

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

20. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Dennis

AED 338

AED 385 total

includes taxes & fees

11 Nov - 12 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 1,003 reviews	View
Flag House Inn	9.2 Wonderful 98 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,055 reviews	View

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"Nice place very cool place!"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"

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

10/10 Excellent

"Excellent location. Perfect property. Very hard to rate price for value as a five because I was their during the sailboat show and all prices are (gulp) astronomical. I’m sure the pricing is better at other times. Overall, great stay. Perfect if you are visiting Eastport or downtown Annapolis."

Beautiful Condo - Water View Near City Dock

10/10 Excellent

"I think this was a great value and an excellent location. We were there for the powerboat show and this couldn’t have been more convenient. The place was well stocked and had everything we needed and was very very clean."

Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

10/10 Excellent

"Great place. Close to Annapolis and great layout for our 4 grandkids and parents."

Eastport Cottage .5 mi from Downtown Annapolis

10/10 Excellent

"Great location. Very communicative host"

Walk to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard

10/10 Excellent

"Our stay was perfect. A beautiful, clean home within walking distance to everything. The house had everything we needed. We went for a girls weekend and it was everyone’s first time in Annapolis and we all can’t wait to bring our families back next time."

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

8/10 Good

"Nice neighborhood. Charming house . Was missing a few basics such as hand soap , soap, and shampoo in the showers, tissue paper. Was a little confused with food left in the refrigerator if it was complementary, or was for purchase. Was a little difficult opening up the key box for someone not familiar with how that works. Could've used a little better description. Finally, the foldout Sofa has a very thin mattress, and only sleeps one . It was But overall, the house worked well for our family."

Bay View Studio Apartment

10/10 Excellent

"Our second time here and won't be our last. Great place for a relaxing get away. Location is spectacular and patio is essentially in the water. Host is very cognizant of their guests and their privacy. Plenty of food options in close proximity (highly recommend black market bakery), but there is a grill and fully stocked kitchen if you want to prepare your own meals like we did. The host is quick to respond with any questions you may have. The hot tub and kayaks provide entertainment for all adventure levels. Can't wait to visit again!"

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 savor 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 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.

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, check out the 88 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 88 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.

Find hotels near Annapolis Sailing School, Annapolis from AED 370

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Treat yourself

Be picky

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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. The Westin Annapolis

10. Hilton Garden Inn Annapolis Downtown

11. The Inn at Chesapeake Bay Beach Club

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

13. Kent Island Resort

14. SpringHill Suites by Marriott Annapolis

15. TownePlace Suites by Marriott Annapolis

16. Crowne Plaza Annapolis by IHG

17. DoubleTree by Hilton Hotel Annapolis

18. Candlewood Suites Annapolis by IHG

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

20. Sonesta ES Suites Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

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

Beautiful Condo - Water View Near City Dock

Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

Eastport Cottage .5 mi from Downtown Annapolis

Walk to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard

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

Bay View Studio Apartment

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