The Best Hotels Closest to 14 Fleet Street in Annapolis for 2026

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Our top choices for 14 Fleet Street hotels

A brick building with a large window and a dome in the background.

A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.

A cozy lounge area with a cushioned bench, two small tables with lamps, a brick wall, and a fireplace.

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, 0.3 km from 14 Fleet Street

Angela

￥43,909

￥50,057 total

includes taxes & fees

Oct 27 - Oct 28

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 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.

2. Graduate by Hilton Annapolis

0.9 km from 14 Fleet Street

Nadine

￥21,720

￥24,760 total

includes taxes & fees

Nov 22 - Nov 23

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 dark blue bookshelf with decorative items and books.

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

3. Flag House Inn

Historic District, 0.2 km from 14 Fleet Street

Thomas

￥35,611

￥40,597 total

includes taxes & fees

Oct 26 - Oct 27

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

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

4. Residence Inn By Marriott Annapolis

1.5 km from 14 Fleet Street

Caitlin

￥21,159

￥24,121 total

includes taxes & fees

Nov 1 - Nov 2

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.

5. Fairfield Inn & Suites By Marriott Annapolis

1.5 km from 14 Fleet Street

Imola

￥19,905

￥22,691 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

6. The Westin Annapolis

1.4 km from 14 Fleet Street

Bobbi

￥26,487

￥30,195 total

includes taxes & fees

Nov 22 - Nov 23

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.

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

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

7. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 0.3 km from 14 Fleet Street

William

￥33,728

￥38,451 total

includes taxes & fees

Nov 23 - Nov 24

A two-story house with a front porch, large windows, and a well-maintained lawn.

A cozy living room with a fireplace, two patterned armchairs, a coffee table with a vase, and a bookshelf.

A house with a covered porch, outdoor seating, and string lights.

A modern living room with a grey sofa, a coffee table, and a bookshelf filled with books and decorative items.

8. 1313 West Luxury Boutique Hotel

Homewood, 2.3 km from 14 Fleet Street

Sheila

￥41,004

￥46,744 total

includes taxes & fees

Oct 25 - Oct 26

An outdoor patio area with seating arrangements and a fire feature.

A hotel room with two beds, a desk, a TV, and a bathroom.

A reception area with two wooden reception desks, a stone wall, and a modern ceiling design.

A modern bar area with a wooden counter, bar stools, a television screen, and a variety of beverages.

9. Courtyard by Marriott Bowie

19.4 km from 14 Fleet Street

Halima

￥21,017

￥23,750 total

includes taxes & fees

Nov 8 - Nov 9

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 balcony with a view of a marina filled with boats.

10. The Inn at Chesapeake Bay Beach Club

14 km from 14 Fleet Street

scott

￥33,513

￥41,187 total

includes taxes & fees

Nov 15 - Nov 16

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 modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

18.2 km from 14 Fleet Street

Tucker

￥13,455

￥15,338 total

includes taxes & fees

Nov 23 - Nov 24

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 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.

12. Kent Island Resort

14.2 km from 14 Fleet Street

Bethany

￥19,178

￥26,469 total

includes taxes & fees

Nov 16 - Nov 17

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.

13. TownePlace Suites by Marriott Annapolis

5.5 km from 14 Fleet Street

Nkusu Lauren

￥18,494

￥21,083 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

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

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.

14. SpringHill Suites by Marriott Annapolis

5.4 km from 14 Fleet Street

Kaiya

￥17,185

￥19,591 total

includes taxes & fees

Nov 15 - Nov 16

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 Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

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

6 km from 14 Fleet Street

Catherine

￥13,040

￥14,865 total

includes taxes & fees

Nov 23 - Nov 24

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

A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.

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

A well-lit snack and beverage kiosk with a variety of snacks and drinks, including bottled water, juices, and snacks.

16. Crowne Plaza Annapolis by IHG

4.9 km from 14 Fleet Street

Jose

￥16,143

￥18,402 total

includes taxes & fees

Nov 22 - Nov 23

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 hotel sign for Candlewood Suites with a modern building in the background.

An outdoor patio with a covered seating area, grill stations, and planters.

17. Candlewood Suites Annapolis by IHG

5.1 km from 14 Fleet Street

Darren

￥13,165

￥15,781 total

includes taxes & fees

Nov 1 - Nov 2

18. Laurel Grove Inn on the South

8.4 km from 14 Fleet Street

Ruth

￥28,211

￥32,161 total

includes taxes & fees

Nov 11 - Nov 12

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

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

A gym with treadmills, weight machines, and dumbbells.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

19. Sonesta ES Suites Annapolis

5.5 km from 14 Fleet Street

Ann Christine

￥13,479

￥15,366 total

includes taxes & fees

Nov 16 - Nov 17

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

20. Courtyard by Marriott Annapolis

5.7 km from 14 Fleet Street

Jim

￥15,723

￥17,924 total

includes taxes & fees

Nov 9 - Nov 10

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Compare popular hotels close to 14 Fleet Street

Property	Star rating	Guest rating
86 State Circle - Luxury Boutique Hotel	10.0 Exceptional 10 reviews	View
Graduate by Hilton Annapolis	9.4 Exceptional 1,008 reviews	View
Flag House Inn	9.2 Wonderful 99 reviews	View
Residence Inn By Marriott Annapolis	9.0 Wonderful 93 reviews	View
Fairfield Inn & Suites By Marriott Annapolis	8.8 Excellent 247 reviews	View

Top 14 Fleet Street Hotel Reviews

134 Prince - Luxury Boutique Hotel

8/10 Good

"A lovely property though not staffed full time. Some maintenance issues that were eventually resolved. Coffee and pastries available but not breakfast. Location was perfect for walking around town."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Easy access to downtown, Great waterside restaurants."

Flag House Inn

10/10 Excellent

"Great location in the heart of old Annapolis. Courtesy staff that were very friendly and helpful. A clean, relaxing room every day. Thank you!"

Boutique Cedar Home 2 blocks from City Dock, USNA & Main Street w Parking

10/10 Excellent

"We stayed at the cedar house for my daughter’s wedding at the Naval Academy, we would love to return to this house to vacation in Annapolis. It is perfectly located and we had access by walking to all of our events. Cathy and Sean from Itrip were more than helpful. I cannot express how much they helped make this trip less stressful. Given that it was the sail boat show, Cathy stayed in touch and we were able to secure early entry. Thank you!! The first floor was large enough for pre wedding gatherings. The Harry Potter bathroom was very convent. This is a historic house with stairs. The second floor was beautifully decorated and the suite on the third floor was incredibly comfy. We had plenty of towels and toiletries. Check out was easy and finding the garbage cans is not hard. Can’t wait to return. 5 stars!"

Walk to Main St, City Dock, USNA from Historic Catch 22 w Private Patio

10/10 Excellent

"We had four travelers stay here. The place was as listed and was clean and plenty roomy. Since we enjoy cooking immensely, we found the kitchenware to be just adequate. For example, there was no large pot for pasta or other big boils, and there might have been Corning-ware or the like but we didn’t find it. There was one cookie sheet and the sole cutting board was a single glass one. Plus oddly, there was no liquid dish soap. We made do in the kitchen. The grill was clean and operable and the appliances functioned excellently. Toiletries were skimpy as well. For a space this size there were only two washcloths, and even though we were warned that there would be sample size soaps and body-wash, there were none at all. Despite the workarounds all other things connected with this location were great!"

Go Navy! Steps to USNA, City Dock & Street Parking

10/10 Excellent

"From the moment you walk onto Fleet Street....you are transported to charming history of Downtown Annapolis. The Fleets Inn was perfect for our USNA family visit. The attention to detail was evident around every corner. From the USNA decor, fully equipped kitchen, comfortable lounging in the living room, comfortable sleeping. Truly a gem in DTA. The owners are a USNA family and made our stay ever so welcoming. Five stars for Fleets Inn."

Naval Academy Gate 1

10/10 Excellent

"Property was in a great location, walking distance from everything downtown. It was clean and everything worked the way that it should."

Historic Row Home in Downtown Annapolis

10/10 Excellent

"Great little house on a perfect location"

18th Cent. Charm in Historic Downtown Annapolis

10/10 Excellent

"Great location and very clean,"

Other attractions near 14 Fleet Street

A white building with a dome, surrounded by lush greenery and a well-maintained garden with pathways and benches.

William Paca House

8.6/10 (24 reviews)

Learn about the life and explore the historic home of 18th-century lawyer and signer of the Declaration of Independence, William Paca.

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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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48 Fleet Street

Learn about the local history of Annapolis when you spend time at 48 Fleet Street.

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Annapolis City Dock

9.4/10 (1,099 reviews)

You can search for that perfect souvenir at Annapolis City Dock during your visit to Annapolis. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

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John Smith House

Find out about the history of Annapolis with a stop at John Smith House.

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97, 99 and 101 East Street

8.0/10 (1 review)

Find out about the history of Annapolis when you take a trip to 97, 99 and 101 East Street.

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The Colonial Players

9.0/10 (2 reviews)

Get tickets for a show at The Colonial Players, a storied theater in Annapolis. While you're in the area, stroll along the waterfront.

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Maryland Federation of Art

8.0/10 (1 review)

You can study the exhibits at Maryland Federation of Art, a museum with a storied past, during your trip to Annapolis. While you're in the area, stroll along the waterfront.

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Frequently asked questions

What's the area like around 14 Fleet Street?

14 Fleet Street is located in Annapolis. If you're looking for a convenient place to stay, check out the 277 hotels and other accommodations you'll find within a mile.

What's the best place to stay near 14 Fleet Street?

Adjacent to 14 Fleet Street, Historic Inns of Annapolis is one of the top choices for your stay based on our traveler data, and this hotel offers a 24-hour fitness center and a bar. Other good choices within a short distance include Graduate by Hilton Annapolis and Annapolis Waterfront Hotel, Autograph Collection.

How many hotels will I be able to find close to 14 Fleet Street?

Expedia has 277 hotels and other accommodations within a mile from 14 Fleet Street.

If I need to cancel the hotel reservation for my stay near 14 Fleet Street, will I receive a refund?

Yes! Most room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Add dates, click "Search", then use the filter option "fully refundable" to review the best options available near 14 Fleet Street.

Where can I learn more about changing or cancelling my trip in the area near 14 Fleet Street?

For more information about changing or cancelling your stay near 14 Fleet Street, head over to our customer service page.

What can I see and do near 14 Fleet Street?

You might want to spend some time browsing the exhibits at Annapolis Maritime Museum, Hammond-Harwood House, or London Town. Explore landmarks like William Paca House, 97, 99 and 101 East Street, and 48 Fleet Street. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.

Find hotels near 14 Fleet Street, Annapolis from ￥14,865

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Our top choices for 14 Fleet Street hotels

1. 86 State Circle - Luxury Boutique Hotel

2. Graduate by Hilton Annapolis

3. Flag House Inn

4. Residence Inn By Marriott Annapolis

5. Fairfield Inn & Suites By Marriott Annapolis

6. The Westin Annapolis

7. Annapolis Waterfront Hotel, Autograph Collection

8. 1313 West Luxury Boutique Hotel

9. Courtyard by Marriott Bowie

10. The Inn at Chesapeake Bay Beach Club

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

12. Kent Island Resort

13. TownePlace Suites by Marriott Annapolis

14. SpringHill Suites by Marriott Annapolis

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

16. Crowne Plaza Annapolis by IHG

17. Candlewood Suites Annapolis by IHG

18. Laurel Grove Inn on the South

19. Sonesta ES Suites Annapolis

20. Courtyard by Marriott Annapolis

Compare popular hotels close to 14 Fleet Street

Top 14 Fleet Street Hotel Reviews

134 Prince - Luxury Boutique Hotel

Annapolis Waterfront Hotel, Autograph Collection

Flag House Inn

Boutique Cedar Home 2 blocks from City Dock, USNA & Main Street w Parking

Walk to Main St, City Dock, USNA from Historic Catch 22 w Private Patio

Go Navy! Steps to USNA, City Dock & Street Parking

Naval Academy Gate 1

Historic Row Home in Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis

Other attractions near 14 Fleet Street

William Paca House

Ego Alley

48 Fleet Street

Annapolis City Dock

John Smith House

97, 99 and 101 East Street

The Colonial Players

Maryland Federation of Art

Frequently asked questions