Annapolis Downtown Vacation Rentals
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Bedrooms
Bathrooms
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Distinctive Features
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5 mi
433 rentals in Annapolis.
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Best Location. Best Price. Across from Gate One & Steps from the Waterfront
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Upscale home with parking for 4 cars in driveway. Walk to downtown.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Cozy Downtown Annapolis Apartment
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Cozy place close to the city dock
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic Downtown Charmer, Water Views and Parking!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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West Annapolis Waterfront Stay with Views, Dock & Boat
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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3 Story Stunner in Murray Hill <1 mile from USNA!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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Historic District Charm with two mid-size or smaller parking spots!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Cozy 1st Floor King George one bedroom apartment right across from USNA
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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ACROSS FROM STADIUM - walk to downtown Annapolis.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Renovated Historic Home located downtown with parking - Walk everywhere !
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Annapolis Condominium in the heart of the historic center
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Waterfront Cottage with Breathtaking Views!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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PERFECT LOCATION in the heart of history
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Annapolis WaterVIEW Home
Rental Home
4 bedrooms
4 bathrooms
Sleeps 14
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Historic Annapolis Home With Two Off-street Parking Places!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Heart of Historic District!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
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Happy days on the Bay at dog-friendly beachfront home on the Chesapeake
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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The Yellow Cottage on Harness Creek
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Bay View Studio Apartment
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Freshly renovated 3-story home 1 block from USNA!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Your Annapolis adventure starts here!!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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La Maison - Stunning waterfront views with pool
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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New rates! Historic happy home, steps to Main Street, parking and lots of
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Little Magothy Riverfront Home With Pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Downtown Annapolis Townhome ! Beautiful!!
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Condo Amazing Views with Resort Amenities
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Affiliated with FlipKey
Location Location Location!!!50 Steps from Main Street and all of the action
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Welcome Aboard the Kathleen Marie!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chic Condo w/ Balcony in the Heart of Annapolis!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Rates! Modern and cozy Captain’s Crossing Cape house in West Annapolis
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Waterfront Annapolis Getaway w / Fishing Pier!
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Nautical Feel to This Beautiful Eastport Home
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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