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Price per night from
$344
Vintage Bungalow-cozy, walk to shops, water, free pkg.
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$476
Perfect Annapolis with Lots of Parking & Hot Tub
Annapolis townhouse
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$796
“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.
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$487
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$1,025
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$1,145
Responds fast! avg. 18 minutes
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$232
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$801
New rates! Historic Union Row House Downtown with Parking and private patio
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 27 minutes
Price per night from
$403
The Fleet's Inn just steps from the Waterfront in this modern Historic home
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Responds fast! avg. 2 hours 27 minutes
Price per night from
$397
Responds fast! avg. 2 hours 27 minutes
Price per night from
$417
New rates! 2 parking spots and Walkable to Main Street at Seashell in the City
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 27 minutes
Price per night from
$195
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$670
Take your Leave of Absence around gardens with driveway parking
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
Responds fast! avg. 2 hours 27 minutes
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$426
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$430
Responds fast! avg. 2 hours 27 minutes
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$639
Hanover House across from USNA Gate 3 with Parking Pass!
Annapolis house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 27 minutes
Price per night from
$382
Pet-friendly Loft in popular Eastport on 2nd Floor
Annapolis apartment
- 2 bedrooms
- 1 bathroom
- sleeps 5
Responds fast! avg. 2 hours 27 minutes
Price per night from
$269
1 Block to USNA with Chapel Views big back patio and off-site parking!
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 7
Responds fast! avg. 2 hours 27 minutes
Price per night from
$415
New Pet-friendly, stunning decor and parking at On Cloud 9
Annapolis house
- 4 bedrooms
- 4 bathrooms
- sleeps 14
Responds fast! avg. 2 hours 27 minutes
Price per night from
$407
New Rates! Modern and cozy Captain’s Crossing Cape house in West Annapolis
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 27 minutes
Price per night from
$406
Now Pet Friendly! Hang just 2 blocks from Navy Stadium all on 1 floor
Annapolis house
- 3 bedrooms
- 1 bathroom
- sleeps 6
Responds fast! avg. 2 hours 27 minutes
Price per night from
$337
Waterfront Condo with pool and parking walkable to all of DTA
Annapolis condo
- 2 bedrooms
- 2 bathrooms
- sleeps 7
Responds fast! avg. 2 hours 27 minutes
Price per night from
$397
Comfort & Luxury near downtown, mall, coffee shops and more
Annapolis apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Price per night from
$195
New Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
Annapolis house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 27 minutes
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$367
Responds fast! avg. 2 hours 27 minutes
Price per night from
$419
Cottage by the Bay on one level in family-friendly community (small dog friendly
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 27 minutes
Price per night from
$367
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$441
Newly-renovated home in Bay Ridge, exclusive water-privileged community
Annapolis house
- 5 bedrooms
- 4 bathrooms
- sleeps 11
Responds fast! avg. 2 hours 27 minutes
Price per night from
$446
New Rates! Historic Carriage House in the center of town with parking
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 27 minutes
Price per night from
$343
Pet-friendly Waterfront Coastal home just minutes to Annapolis
Annapolis house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
Responds fast! avg. 2 hours 27 minutes
Price per night from
$398
Responds fast! avg. 2 hours 27 minutes
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$411
Responds fast! avg. 2 hours 27 minutes
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$382
Responds fast! avg. 2 hours 27 minutes
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$220
Responds fast! avg. 2 hours 27 minutes
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$637
Responds fast! avg. 2 hours 27 minutes
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$629
Responds fast! avg. 2 hours 27 minutes
Price per night from
$394
New Rates! Steps from the water, Easy parking private backyard and pet-friendly
Annapolis house
- 2 bedrooms
- 2 bathrooms
- sleeps 7
Responds fast! avg. 2 hours 27 minutes
Price per night from
$355
Viewing 38 of 121
rentals in Annapolis
About Annapolis
Come to Annapolis to experience the best of old world style and Chesapeake Bay charm. This distinguished town, located on the salty bay, has provided visitors with the perfect Maryland vacation getaway for centuries. Visit the museums here and learn more about the early settlers of the area, the natural history and the wildlife that populate fragile Maryland ecosystems, and the important events in American history that took place here. Find a vacation rental, summer home, or bayside cottage overlooking the shoreline. Head downtown to experience Maryland's annual festivals celebrating regional music and the famous Maryland blue crab. Go antique and craft shopping in the heart of the city. Explore Annapolis museums and art galleries and spend some time on the emerald green golf courses around the Chesapeake Bay. At night, head downtown for world-class seafood and a live performance at a local theater.
Here are a few additional suggestions for your trip:
- Visit the Maryland State House: Annapolis was America's first peacetime capitol, and the statehouse is the oldest still in legislative use.
- Visit the US Naval Academy: Take a tour of the Naval Academy, one of the proud institutions of Annapolis.
- Go on a pirate adventure: Take a real life pirate adventure on a ship in Annapolis Harbor. Pirate Adventures on the Chesapeake offers a full day of true buccaneering on an Annapolis boat, complete with face paint, pirate fashions, and a water cannon battle.
- Experience Annapolis sailing: Nothing can compare with a real sailing adventure aboard an authentic Chesapeake Skipjack. Help man the sails, try your hand at Annapolis fishing and crabbing, or just relax on the deck and watch the harbor birds sail overhead.
- Visit the William Paca Garden: This colonial garden offers peace, serenity, and history lessons along with guided tours.
- Explore Quiet Waters Park: This 340 acre park just outside the city center offers more than six miles of trails perfect for strolling, jogging, or biking.
Thousands of visitors come to this area every year to enjoy long weekend getaways, family reunions, and beautiful wedding venues in Annapolis. If you're among them, find the perfect rental apartment in the heart of downtown, or a bayside condo near the harbor. While you're here, consider visiting a few other popular vacation destinations in Maryland like Arnold and Lake Shore.
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