Annapolis House Rentals
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325 rentals in Annapolis.
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Charming historic home just steps from Main Street!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Charming Historic Annapolis Home With Two Off-street Parking Places!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Gorgeous Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Annapolis waterfront "tiny house" in garden setting
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Stunning Waterfront Cottage with Breathtaking Views!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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The Yellow Cottage on Harness Creek
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
Holiday Rental House
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.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Stunning Home in Historic District, Steps to USNA & Downtown
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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La Maison - Stunning waterfront views with pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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The Cottage on Spa Creek
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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PERFECT LOCATION in the heart of history
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps, Vacation Rental House
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Beautiful Historic Home With Great Location!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Two Blocks to Town, Underground Parking Garage
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Renovated Historic Home located downtown with parking - Walk everywhere !
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Beautiful Waterfront Townhome In Historic Annapolis
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Historic Downtown Charmer, Water Views and Parking!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Tastefully decorated Eastport Annapolis house with water views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Space & Relaxation you Crave ! With plenty of Parking!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Historic Annapolis Home And Garden
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Stunning Annapolis Home! Across from the library, walk to Naval Graduation
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Charming Annapolis Victorian
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Welcome Aboard the Kathleen Marie!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Eastport Cottage .5 mi from Downtown Annapolis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, Vacation Rental House
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Historic District Home with Gorgeous Renovation
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Heart of Historic District!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Charming cottage - easy walk to downtown with parking
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Vacation Rental House
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Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Charming Historic Annapolis with Impressive Updates Throughout
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, Vacation Rental House
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Come enjoy Historic Annapolis!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Walk to Naval Academy + City Dock
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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Walk everywhere . . .just minutes to historic Annapolis, Updated.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Historic District'Crab Cakes and Football'
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Water Views - Close to Downtown Annapolis
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Waterfront Chesapeake Cottage in Oyster Bay - Dock
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, Vacation Rental House
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We Get Repeat Renters!!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Historic Grandeur in the Heart of Downtown
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Annapolis home with ideal historic district locale
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Large Contemporary in Wooded Privacy
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Perfect historic home + Peloton, walk to downtown Annapolis
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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