Pet Friendly Holiday Rentals in Annapolis
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111 rentals in Annapolis.
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Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!
4 bedrooms
3 bathrooms
Sleeps 9
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Annapolis waterfront 'tiny house' in garden setting
1 bedroom
1 bathroom
Sleeps 4
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Charming historic home just steps from Main Street!
3 bedrooms
3 bathrooms
Sleeps 8
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere
2 bedrooms
1 bathroom
Sleeps 4
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Charming Historic Annapolis Home With Two Off-street Parking Places!
3 bedrooms
3 bathrooms
Sleeps 8
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The Yellow Cottage on Harness Creek
2 bedrooms
1 bathroom
Sleeps 6
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Two Blocks to Town, Underground Parking Garage
3 bedrooms
4 bathrooms
Sleeps 6
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PERFECT LOCATION in the heart of history
3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Waterfront Townhome In Historic Annapolis
3 bedrooms
4 bathrooms
Sleeps 8
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
1 bedroom
1 bathroom
Sleeps 4
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Save time - get the best Annapolis rentals sent straight to your email!
Renovated Historic Home located downtown with parking - Walk everywhere !
3 bedrooms
2 bathrooms
Sleeps 7
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
4 bedrooms
4 bathrooms
Sleeps 11
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
5 bedrooms
4 bathrooms
Sleeps 13
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate
4 bedrooms
4 bathrooms
Sleeps 10
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Historic Downtown Charmer, Water Views and Parking!
2 bedrooms
2 bathrooms
Sleeps 5
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool.
5 bedrooms
3 bathrooms
Sleeps 12
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Beautiful Historic Home With Great Location!
4 bedrooms
3 bathrooms
Sleeps 10
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
4 bedrooms
2 bathrooms
Sleeps 9
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The Cottage on Spa Creek
2 bedrooms
2 bathrooms
Sleeps 4
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Impeccable, near Navy Stadium
5 bedrooms
5 bathrooms
Sleeps 10
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Walk Everywhere with Off-Street Parking !!!
3 bedrooms
3 bathrooms
Sleeps 7
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Cozy Cottage by the Beach
2 bedrooms
1 bathroom
Sleeps 4
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Come enjoy Historic Annapolis!
2 bedrooms
2 bathrooms
Sleeps 5
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Historic Annapolis Home And Garden
2 bedrooms
2 bathrooms
Sleeps 6
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Pristine Renovation: Perfect Downtown Location walk to the Academy or Stadium!
4 bedrooms
3 bathrooms
Sleeps 8
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Heart of the Historic District!
5 bedrooms
3 bathrooms
Sleeps 10
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
3 bedrooms
2 bathrooms
Sleeps 6
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
1 bedroom
1 bathroom
Sleeps 2
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Annapolis Condominium in the Heart of Historic Downtown
3 bedrooms
2 bathrooms
Sleeps 6
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Location Location Location!!!50 Steps from Main Street and all of the action
3 bedrooms
2 bathrooms
Sleeps 8
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Welcome Aboard the Kathleen Marie!
2 bedrooms
2 bathrooms
Sleeps 4
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
1 bedroom
1 bathroom
Sleeps 2
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Charming waterfront home located in Downtown Historic Annapolis
3 bedrooms
3 bathrooms
Sleeps 8
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Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
3 bedrooms
2 bathrooms
Sleeps 5
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Walk to Naval Academy + City Dock
3 bedrooms
3 bathrooms
Sleeps 7
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
2 bedrooms
3 bathrooms
Sleeps 5
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Extended Stays Available Please contact for Availability and Pricing.
1 bedroom
1 bathroom
Sleeps 4
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Walk everywhere . . .just minutes to historic Annapolis, Updated.
2 bedrooms
2 bathrooms
Sleeps 4
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0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!
4 bedrooms
3 bathrooms
Sleeps 8
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Sleeps 10! Great Reviews.
4 bedrooms
4 bathrooms
Sleeps 10
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
2 bedrooms
1 bathroom
Sleeps 5
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Charming Historic Annapolis with Impressive Updates Throughout
5 bedrooms
4 bathrooms
Sleeps 14
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Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn
4 bedrooms
3 bathrooms
Sleeps 10
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Heart of Downtown, superior location!
4 bedrooms
3 bathrooms
Sleeps 10
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Historic beach Cottage
3 bedrooms
2 bathrooms
Sleeps 8
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Eastport Cottage .5 mi from Downtown Annapolis
2 bedrooms
1 bathroom
Sleeps 3
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Large Luxury Apartment In Downtown Annapolis
2 bedrooms
2 bathrooms
Sleeps 4
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Waterside with it All! Private Pier, Hot Tub and Pool.
6 bedrooms
6 bathrooms
Sleeps 18
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Casual Coastal Living in Historic Eastport/Annapolis
4 bedrooms
3 bathrooms
Sleeps 10
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0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock.
6 bedrooms
7 bathrooms
Sleeps 14
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