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Annapolis House Rentals

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346 rentals in Annapolis.
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Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, vacation rental in Annapolis

Charming Historic Annapolis Home With Two Off-street Parking Places!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis

Annapolis waterfront "tiny house" in garden setting

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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The Yellow Cottage on Harness Creek, vacation rental in Annapolis
The Yellow Cottage on Harness Creek, vacation rental in Annapolis
The Yellow Cottage on Harness Creek, vacation rental in Annapolis

The Yellow Cottage on Harness Creek

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, vacation rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis

Welcome Aboard the Kathleen Marie!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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La Maison - Stunning waterfront views with pool, vacation rental in Annapolis
La Maison - Stunning waterfront views with pool, vacation rental in Annapolis
La Maison - Stunning waterfront views with pool, vacation rental in Annapolis

La Maison - Stunning waterfront views with pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Charming historic home  just steps from Main Street!, vacation rental in Annapolis
Charming historic home  just steps from Main Street!, vacation rental in Annapolis
Charming historic home  just steps from Main Street!, vacation rental in Annapolis

Charming historic home just steps from Main Street!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Large Contemporary in Wooded Privacy, vacation rental in Annapolis
Large Contemporary in Wooded Privacy, vacation rental in Annapolis
Large Contemporary in Wooded Privacy, vacation rental in Annapolis

Large Contemporary in Wooded Privacy

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis
Beautiful Waterfront Townhome In Historic Annapolis, vacation rental in Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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We Get Repeat Renters!!, vacation rental in Annapolis
We Get Repeat Renters!!, vacation rental in Annapolis
We Get Repeat Renters!!, vacation rental in Annapolis

We Get Repeat Renters!!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Charming Annapolis Victorian, vacation rental in Annapolis
Charming Annapolis Victorian, vacation rental in Annapolis
Charming Annapolis Victorian, vacation rental in Annapolis

Charming Annapolis Victorian

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Water Views - Close to Downtown Annapolis, vacation rental in Annapolis
Water Views - Close to Downtown Annapolis, vacation rental in Annapolis
Water Views - Close to Downtown Annapolis, vacation rental in Annapolis

Water Views - Close to Downtown Annapolis

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Beautiful Historic Home With Great Location!, vacation rental in Annapolis
Beautiful Historic Home With Great Location!, vacation rental in Annapolis
Beautiful Historic Home With Great Location!, vacation rental in Annapolis

Beautiful Historic Home With Great Location!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !, vacation rental in Annapolis

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Tastefully decorated Eastport Annapolis house with water views, vacation rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, vacation rental in Annapolis
Tastefully decorated Eastport Annapolis house with water views, vacation rental in Annapolis

Tastefully decorated Eastport Annapolis house with water views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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The Cottage on Spa Creek, vacation rental in Annapolis
The Cottage on Spa Creek, vacation rental in Annapolis
The Cottage on Spa Creek, vacation rental in Annapolis

The Cottage on Spa Creek

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, vacation rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue, vacation rental in Annapolis
Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue, vacation rental in Annapolis
Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue, vacation rental in Annapolis

Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Walk to Naval Academy + City Dock, vacation rental in Annapolis
Walk to Naval Academy + City Dock, vacation rental in Annapolis
Walk to Naval Academy + City Dock, vacation rental in Annapolis

Walk to Naval Academy + City Dock

Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps, Vacation Rental House
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Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis
Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA, vacation rental in Annapolis

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Vacation Rental House
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Heart of Historic District!, vacation rental in Annapolis
Heart of Historic District!, vacation rental in Annapolis
Heart of Historic District!, vacation rental in Annapolis

Heart of Historic District!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, Vacation Rental House
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Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis
Charming Historic Annapolis with Impressive Updates Throughout, vacation rental in Annapolis

Charming Historic Annapolis with Impressive Updates Throughout

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, Vacation Rental House
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Historic District Renovated Home Available for 2023 Legislative Session, vacation rental in Annapolis
Historic District Renovated Home Available for 2023 Legislative Session, vacation rental in Annapolis
Historic District Renovated Home Available for 2023 Legislative Session, vacation rental in Annapolis

Historic District Renovated Home Available for 2023 Legislative Session

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, vacation rental in Annapolis
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, vacation rental in Annapolis
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, vacation rental in Annapolis

Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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PERFECT LOCATION in the heart of history, vacation rental in Annapolis
PERFECT LOCATION in the heart of history, vacation rental in Annapolis
PERFECT LOCATION in the heart of history, vacation rental in Annapolis

PERFECT LOCATION in the heart of history

Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps, Vacation Rental House
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Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis
Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis
Two Blocks to Town, Underground Parking Garage, vacation rental in Annapolis

Two Blocks to Town, Underground Parking Garage

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, vacation rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, vacation rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, vacation rental in Annapolis

Best Location. Best Price. Across from Gate One & Steps from the Waterfront

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Upscale home with parking for 4 cars in driveway.  Walk to downtown., vacation rental in Annapolis
Upscale home with parking for 4 cars in driveway.  Walk to downtown., vacation rental in Annapolis
Upscale home with parking for 4 cars in driveway.  Walk to downtown., vacation rental in Annapolis

Upscale home with parking for 4 cars in driveway. Walk to downtown.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Space & Relaxation you Crave ! With plenty of Parking!, vacation rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, vacation rental in Annapolis
Space & Relaxation you Crave ! With plenty of Parking!, vacation rental in Annapolis

Space & Relaxation you Crave ! With plenty of Parking!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Now Available Commissioning Week 2023! (May 19th to May 27th), vacation rental in Annapolis
Now Available Commissioning Week 2023! (May 19th to May 27th), vacation rental in Annapolis
Now Available Commissioning Week 2023! (May 19th to May 27th), vacation rental in Annapolis

Now Available Commissioning Week 2023! (May 19th to May 27th)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Stunning Home in Historic District, Steps to USNA & Downtown, vacation rental in Annapolis
Stunning Home in Historic District, Steps to USNA & Downtown, vacation rental in Annapolis
Stunning Home in Historic District, Steps to USNA & Downtown, vacation rental in Annapolis

Stunning Home in Historic District, Steps to USNA & Downtown

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Historic Annapolis Home And Garden, vacation rental in Annapolis
Historic Annapolis Home And Garden, vacation rental in Annapolis
Historic Annapolis Home And Garden, vacation rental in Annapolis

Historic Annapolis Home And Garden

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Beautiful Eastport Home walking distance to downtown and USNA. Includes parking, vacation rental in Annapolis
Beautiful Eastport Home walking distance to downtown and USNA. Includes parking, vacation rental in Annapolis
Beautiful Eastport Home walking distance to downtown and USNA. Includes parking, vacation rental in Annapolis

Beautiful Eastport Home walking distance to downtown and USNA. Includes parking

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis, vacation rental in Annapolis

Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Lovely Family Home Just Minutes From Annapolis, vacation rental in Annapolis
Lovely Family Home Just Minutes From Annapolis, vacation rental in Annapolis
Lovely Family Home Just Minutes From Annapolis, vacation rental in Annapolis

Lovely Family Home Just Minutes From Annapolis

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, vacation rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, vacation rental in Annapolis
THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, vacation rental in Annapolis

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, vacation rental in Annapolis
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, vacation rental in Annapolis
Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis, vacation rental in Annapolis

Parking and Pet Friendly Renovated Eastport Firehouse in Annapolis

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Stunning Annapolis Home! Across from the library, walk to Naval Graduation, vacation rental in Annapolis
Stunning Annapolis Home! Across from the library, walk to Naval Graduation, vacation rental in Annapolis
Stunning Annapolis Home! Across from the library, walk to Naval Graduation, vacation rental in Annapolis

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Historic District"Crab Cakes and Football", vacation rental in Annapolis
Historic District"Crab Cakes and Football", vacation rental in Annapolis
Historic District"Crab Cakes and Football", vacation rental in Annapolis

Historic District"Crab Cakes and Football"

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, vacation rental in Annapolis

Location Location Location!!!50 Steps from Main Street and all of the action

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis
Eastport Cottage .5 mi from Downtown Annapolis, vacation rental in Annapolis

Eastport Cottage .5 mi from Downtown Annapolis

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, Vacation Rental House
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Enjoy the convenience of being forty yards from the US Naval Academy Barry Gate, vacation rental in Annapolis
Enjoy the convenience of being forty yards from the US Naval Academy Barry Gate, vacation rental in Annapolis
Enjoy the convenience of being forty yards from the US Naval Academy Barry Gate, vacation rental in Annapolis

Enjoy the convenience of being forty yards from the US Naval Academy Barry Gate

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Historic Downtown Annapolis Home for Rent- Steps to Naval Academy, vacation rental in Annapolis
Historic Downtown Annapolis Home for Rent- Steps to Naval Academy, vacation rental in Annapolis
Historic Downtown Annapolis Home for Rent- Steps to Naval Academy, vacation rental in Annapolis

Historic Downtown Annapolis Home for Rent- Steps to Naval Academy

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, Vacation Rental House
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Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis
Walk everywhere . . .just minutes to historic Annapolis,  Updated., vacation rental in Annapolis

Walk everywhere . . .just minutes to historic Annapolis, Updated.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Charming cottage - easy walk to downtown with parking, vacation rental in Annapolis
Charming cottage - easy walk to downtown with parking, vacation rental in Annapolis
Charming cottage - easy walk to downtown with parking, vacation rental in Annapolis

Charming cottage - easy walk to downtown with parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps, Vacation Rental House
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