The Best Hotels Closest to 14 Fleet Street in Annapolis - 2026 Updated Prices

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Our top choices for 14 Fleet Street hotels

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

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

A church with a spire, surrounded by trees and illuminated by warm lights.

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, 0.2 mi from 14 Fleet Street

£247

includes taxes & fees

6 Oct - 7 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

< 0.1 mi from 14 Fleet Street

Chris

£183

includes taxes & fees

4 Oct - 5 Oct

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

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.

A dark blue bookshelf with decorative items and books.

3. Flag House Inn

Historic District, 0.1 mi from 14 Fleet Street

Nathan

£195

includes taxes & fees

4 Oct - 5 Oct

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

A historic brick building with a red roof, multiple windows, and a central staircase.

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.

4. Historic Inns of Annapolis

Historic District, 0.1 mi from 14 Fleet Street

Ashley

£117

includes taxes & fees

12 Oct - 13 Oct

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

5. The Westin Annapolis

0.9 mi from 14 Fleet Street

Bobbi

£171

includes taxes & fees

25 Oct - 26 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.

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.

6. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 0.2 mi from 14 Fleet Street

William

£233

includes taxes & fees

12 Oct - 13 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 restaurant with a yellow cushioned bench, wooden tables, and chairs.

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

7. Hilton Garden Inn Annapolis Downtown

0.7 mi from 14 Fleet Street

petra

£105

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A dining area with a fireplace, framed botanical prints, and a vase with flowers.

8. 1313 West Luxury Boutique Hotel

Homewood, 1.4 mi from 14 Fleet Street

Sheila

£224

includes taxes & fees

4 Oct - 5 Oct

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

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

A Courtyard by Marriott hotel with a curved entrance, multiple floors, and a brick facade.

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

9. Courtyard by Marriott Bowie

12.1 mi from 14 Fleet Street

Halima

£114

includes taxes & fees

19 Oct - 20 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 residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

10. The Inn at Chesapeake Bay Beach Club

8.7 mi from 14 Fleet Street

scott

£180

includes taxes & fees

19 Oct - 20 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.

11. Microtel Inn & Suites by Wyndham Gambrills/Odenton

11.3 mi from 14 Fleet Street

Mark

£81

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

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.

12. TownePlace Suites by Marriott Annapolis

3.4 mi from 14 Fleet Street

Nkusu Lauren

£107

includes taxes & fees

28 Oct - 29 Oct

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 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.

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

3.7 mi from 14 Fleet Street

Leslie

£82

includes taxes & fees

20 Oct - 21 Oct

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

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

14. DoubleTree by Hilton Hotel Annapolis

3.1 mi from 14 Fleet Street

Michele

£77

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

15. Crowne Plaza Annapolis by IHG

3.1 mi from 14 Fleet Street

Cynthia

£95

includes taxes & fees

4 Oct - 5 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 gym with weight racks, benches, and exercise equipment.

A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

16. Candlewood Suites Annapolis by IHG

3.2 mi from 14 Fleet Street

Darren

£91

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

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

A gym with treadmills, weight machines, and dumbbells.

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

17. Sonesta ES Suites Annapolis

3.4 mi from 14 Fleet Street

Philip

£78

includes taxes & fees

28 Oct - 29 Oct

18. Laurel Grove Inn on the South

5.2 mi from 14 Fleet Street

Ruth

£155

includes taxes & fees

4 Oct - 5 Oct

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

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

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

19. Courtyard by Marriott Annapolis

3.5 mi from 14 Fleet Street

Jim

£98

includes taxes & fees

6 Oct - 7 Oct

A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

A hotel lobby with a dining area, a fireplace, and a view of the outside.

A pool table with balls, a pool cue, and three framed pictures on the wall.

A hotel room with two desks, two chairs, a carpeted floor, and artwork on the wall.

20. Hampton Inn & Suites Annapolis

3.3 mi from 14 Fleet Street

Courtney

£90

includes taxes & fees

28 Oct - 29 Oct

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Compare popular hotels close to 14 Fleet Street

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
Flag House Inn	9.2 Wonderful 97 reviews	View
Historic Inns of Annapolis	9.0 Wonderful 2,028 reviews	View
The Westin Annapolis	8.8 Excellent 1,000 reviews	View

Top 14 Fleet Street Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"Parking You will have to use a garage or pay hotel $50.00 per night"

Graduate by Hilton Annapolis

10/10 Excellent

"V"

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."

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

10/10 Excellent

"We enjoyed our stay! The home was clean, comfortable with a very convenient location. Communication was quick and smooth throughout. We would recommend it to future guests."

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

10/10 Excellent

"The location of this property was perfect. The home was clean and nicely appointed. Communication with management company was excellent. My only suggestion would be to provide down pillows. Thank you for a wonderful stay"

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

134 Prince - Luxury Boutique Hotel

10/10 Excellent

"Lovely hotel with incredible staff"

Naval Academy Gate 1

10/10 Excellent

"The property was very clean. We loved the location as we wanted to be in walking distance of DTA and USNA. The host was responsive when we contacted him. I would stay again as we greatly enjoyed our time in Annapolis."

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.

10/10 Excellent

"This property was perfect for my son’s wedding weekend! It was so centrally located and had every amenity. The beds were comfy and the bathrooms were beautiful. Having the porches was such a bonus. Our only hitch was fitting the cars into the parking area. Shorter vehicles work best. Thanks for a great stay!"

Other attractions near 14 Fleet Street

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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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 enjoy retail therapy at Annapolis City Dock during your trip to Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

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Kunta Kinte Plaque & Alex Haley Memorial

You can find out about the history of Annapolis when you stop by Kunta Kinte Plaque & Alex Haley Memorial.

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John Smith House

Find out about the history of Annapolis when you spend time 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 popular theatre 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 holiday in 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, take a look at the 277 hotels and other accommodation options you'll find within a mile.

Where is 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 traveller data, and this hotel offers a 24-hour fitness centre and a bar. Other good options within a short distance include Graduate by Hilton Annapolis and Annapolis Waterfront Hotel, Autograph Collection.

How many hotels can I expect to find close to 14 Fleet Street?

Expedia has 277 hotels and other accommodation options 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! The majority of room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you booked a non-refundable reservation, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available near 14 Fleet Street.

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.

Search Hotels Near 14 Fleet Street, Annapolis

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for 14 Fleet Street hotels

1. 86 State Circle - Luxury Boutique Hotel

2. 134 Prince - Luxury Boutique Hotel

3. Flag House Inn

4. Historic Inns of Annapolis

5. The Westin Annapolis

6. Annapolis Waterfront Hotel, Autograph Collection

7. Hilton Garden Inn Annapolis Downtown

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. TownePlace Suites by Marriott Annapolis

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

14. DoubleTree by Hilton Hotel Annapolis

15. Crowne Plaza Annapolis by IHG

16. Candlewood Suites Annapolis by IHG

17. Sonesta ES Suites Annapolis

18. Laurel Grove Inn on the South

19. Courtyard by Marriott Annapolis

20. Hampton Inn & Suites Annapolis

Compare popular hotels close to 14 Fleet Street

Top 14 Fleet Street Hotel Reviews

Historic Inns of Annapolis

Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

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

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

The Westin Annapolis

134 Prince - Luxury Boutique Hotel

Naval Academy Gate 1

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.

Other attractions near 14 Fleet Street

William Paca House

48 Fleet Street

Annapolis City Dock

Kunta Kinte Plaque & Alex Haley Memorial

John Smith House

97, 99 and 101 East Street

The Colonial Players

Maryland Federation of Art

Frequently asked questions