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 bathroom with a white sink, a toilet, a bathtub, and a glass-enclosed shower area.

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

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.

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

AED 1,132

AED 1,290 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 bookshelf with books, decorative items, and a fireplace.

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.

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

AED 1,238

AED 1,411 total

includes taxes & fees

13 Oct - 14 Oct

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

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.

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Mark

AED 539

AED 615 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 dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.

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

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

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Nathan

AED 857

AED 978 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

AED 315

AED 484 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

A store with shelves of beverages, a counter with a cash register, and baskets with items.

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

8. The Westin Annapolis

2.7 km from Annapolis Sailing School

Bobbi

AED 731

AED 833 total

includes taxes & fees

25 Oct - 26 Oct

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

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

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

9. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

William

AED 820

AED 935 total

includes taxes & fees

26 Oct - 27 Oct

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

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

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

petra

AED 389

AED 443 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 bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

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 749

AED 925 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 reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

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.

12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

paul

AED 328

AED 374 total

includes taxes & fees

3 Nov - 4 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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.

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 445

AED 615 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 room with a bed, a desk, a chair, a coffee machine, and a tray table.

A hotel pool area with two pools, chairs, and a sunshade.

14. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Lisa

AED 437

AED 498 total

includes taxes & fees

1 Nov - 2 Nov

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 modern kitchen with a white countertop, stainless steel appliances, and wooden cabinets.

15. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Nkusu Lauren

AED 419

AED 477 total

includes taxes & fees

19 Oct - 20 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 modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

16. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Jose

AED 386

AED 440 total

includes taxes & fees

25 Oct - 26 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.

17. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Michele

AED 392

AED 446 total

includes taxes & fees

18 Oct - 19 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.

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

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 342

AED 408 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 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 swimming pool with a tiled edge, wooden chairs, and tables around it.

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

A gym with treadmills, weight machines, and dumbbells.

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

Philip

AED 334

AED 381 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 47 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 2,043 reviews	View

Top Annapolis Sailing School Hotel Reviews

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!"

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."

Waterfront 2-Bedroom Condo on Spa Creek

10/10 Excellent

"Beautiful condo in an incredible location. It was very easy to walk to downtown as well as local restaurants and a bakery for breakfast. I did not realize the second bedroom is a pull-out sofa only (my error for not digging into the website particulars). Marie was very understanding, however, there were not any other accommodations available. I can not speak enough about the beauty of the location and the peaceful atmosphere."

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."

Walk Everywhere From Eastport Cape Cod with Gourmet Kitchen

10/10 Excellent

"Was just perfect!! Stayed there twice this summer! Loved being there! So clean and has everything you need."

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.

See properties

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 374

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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. Annapolis Waterfront Hotel, Autograph Collection

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

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

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

Waterfront 2-Bedroom Condo on Spa Creek

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

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