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

1. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

princess

AED 539

AED 615 total

includes taxes & fees

26 Oct - 27 Oct

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 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.

2. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19.7 km from Annapolis Sailing School

Mark

AED 343

AED 391 total

includes taxes & fees

12 Oct - 13 Oct

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 spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

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

3. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

scott

AED 702

AED 873 total

includes taxes & fees

19 Oct - 20 Oct

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

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.

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.

4. Kent Island Resort

13.1 km from Annapolis Sailing School

Bethany

AED 546

AED 730 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

5. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Cynthia

AED 433

AED 494 total

includes taxes & fees

12 Oct - 13 Oct

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

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

6. 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

A modern living room with a large window, a dining area, and a kitchen in the background.

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

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.

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

A hotel entrance with a covered walkway, a flag, and a landscaped area with trees.

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.

8. Holiday Inn Express & Suites Annapolis by IHG

6 km from Annapolis Sailing School

Omer

AED 371

AED 423 total

includes taxes & fees

6 Oct - 7 Oct

9. 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

AED 305

AED 348 total

includes taxes & fees

4 Oct - 5 Oct

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

A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

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

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

10. Best Western Annapolis

6.4 km from Annapolis Sailing School

Sanaul

AED 294

AED 335 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with two beds, a desk, a television, and a window with curtains.

A hallway with a stainless steel refrigerator, a vending machine, and a door.

A hotel hallway with carpeted floors, doors on both sides, and overhead lighting.

A hotel safety and health protocol document.

11. Red Roof Inn Annapolis

6.5 km from Annapolis Sailing School

Slobodan

AED 272

AED 310 total

includes taxes & fees

4 Oct - 5 Oct

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Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
Graduate by Hilton Annapolis	9.4 Exceptional 1,016 reviews	View
Microtel Inn & Suites by Wyndham Gambrills/Odenton	9.2 Wonderful 1,156 reviews	View
The Inn at Chesapeake Bay Beach Club	9.4 Exceptional 499 reviews	View
Kent Island Resort	9.2 Wonderful 187 reviews	View
Crowne Plaza Annapolis by IHG	8.8 Excellent 1,000 reviews	View

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"Loved how the room was decorated and the atrium!"

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."

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

10/10 Excellent

"We had an absolutely incredible stay here over the Naval Academy reunion weekend! The house was the perfect home base for all the festivities. The absolute highlight was the pool area—it was the ultimate spot for hosting classmates, catching up, and relaxing between reunion events. Plus, the location was incredibly convenient; being able to easily hop on the water taxi made getting downtown and back completely seamless. The layout of the home accommodated everyone comfortably, the amenities were fantastic, and the host was incredibly welcoming and communicative. If you’re coming to Annapolis for a Navy weekend, this is the place to stay. Go Navy! Beat Army!"

Eastport Cottage .5 mi from Downtown Annapolis

10/10 Excellent

"Terrific host, amazing location, lovely house."

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."

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."

Bay View Studio Apartment

10/10 Excellent

"Great spot for a couple beautiful location, convenient to downtown and a great peaceful view."

Waterfront 2-Bedroom Condo on Spa Creek

10/10 Excellent

"Fabulous 17 days."

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 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 310

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Annapolis Sailing School hotels

1. Graduate by Hilton Annapolis

2. Microtel Inn & Suites by Wyndham Gambrills/Odenton

3. The Inn at Chesapeake Bay Beach Club

4. Kent Island Resort

5. Crowne Plaza Annapolis by IHG

6. TownePlace Suites by Marriott Annapolis

7. Candlewood Suites Annapolis by IHG

8. Holiday Inn Express & Suites Annapolis by IHG

9. Village Inn Annapolis MD

10. Best Western Annapolis

11. Red Roof Inn Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

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

Eastport Cottage .5 mi from Downtown Annapolis

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

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

Beautiful Condo - Water View Near City Dock

Bay View Studio Apartment

Waterfront 2-Bedroom Condo on Spa Creek

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