Annapolis Holiday Rentals
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465 rentals in Annapolis.
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere
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Best Location. Best Price. Across from Gate One & Steps from the Waterfront
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Upscale home with parking for 4 cars in driveway. Walk to downtown.
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Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
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Cozy place close to the city dock
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Historic Downtown Charmer, Water Views and Parking!
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Amazing views, short walks to great dining!
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3 Story Stunner in Murray Hill <1 mile from USNA!
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Cozy 1st Floor King George one bedroom apartment right across from USNA
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ACROSS FROM STADIUM - walk to downtown Annapolis.
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Sailor's Retreat! Perfect home for the getaway weekend. Best location!
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Renovated Historic Home located downtown with parking - Walk everywhere !
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Annapolis Condominium in the heart of the historic center
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Stunning Waterfront Cottage with Breathtaking Views!
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PERFECT LOCATION in the heart of history
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Charming Annapolis WaterVIEW Home
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Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
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421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
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Charming Historic Annapolis Home With Two Off-street Parking Places!
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Heart of Historic District!
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Jackson's Bunker in Eastport with fenced-in backyard
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Waterfront dog-friendly home with beach just mins to Downtown Annapolis
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The Yellow Cottage on Harness Creek
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Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
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Bay View Studio Apartment
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Freshly renovated 3-story home 1 block from USNA!
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
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La Maison - Stunning waterfront views with pool
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Private yard and screened porch at Historic happy home, steps to Main Street
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
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Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week
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Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
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Downtown Annapolis Townhome ! Beautiful!!
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Location Location Location!!!50 Steps from Main Street and all of the action
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Walk to USNA and Main Street with Parking at Historic Wisteria
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Welcome Aboard the Kathleen Marie!
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Chic Condo w/ Balcony in the Heart of Annapolis!
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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private
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Waterfront Annapolis Home: Fire Pit & Fishing Pier
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Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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Nautical Feel to This Beautiful Eastport Home
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
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Beautiful Historic Home With Great Location!
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Showing results 1-50 of 465
Frequently Asked Questions about Annapolis
- Yes, here are some popular holiday rentals in Annapolis that have a pool:
- Walk to Lake & Boat Ramp: Central Gem in Annapolis
- Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
- Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Yes, here are some popular holiday rentals in Annapolis that have internet access:
- Walk to Lake & Boat Ramp: Central Gem in Annapolis
- Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
- Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- The best pet friendly rentals in Annapolis are:
- Walk to Lake & Boat Ramp: Central Gem in Annapolis
- Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
- Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Some of the most popular kid friendly rentals in Annapolis are:
- Walk to Lake & Boat Ramp: Central Gem in Annapolis
- Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
- Best Location. Best Price. Across from Gate One & Steps from the Waterfront
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