Weems Creek Cottage, Annapolis Waterfront 
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9.8 (11 Reviews) Holiday_home
The entire place is yours • 65 m² size • Free on-site parking
Best Price Match Annapolis Vacation Rentals & NearbyHoliday Homes
Find Vacation Rentals in or near Annapolis. Find vacation rentals in Annapolis, Maryland.
Vintage Charm: Annapolis Retreat Best Price Match
9.7 (10 Reviews) Holiday_home
The entire place is yours • 204 m² size • Free private parking
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Bay Ridge unit by Downtown Annapolis and Quiet Waters Park Best Price Match
9.4 (11 Reviews) Apartment
The entire place is yours • 111 m² size • Free on-site parking
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BayRidge house by Quiet Waters, Thomas Point Parks Best Price Match
8.4 (12 Reviews) Apartment
The entire place is yours • 93 m² size • Free on-site parking
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Cozy 2br home w/ parking in downtown Annapolis Best Price Match
7.0 (6 Reviews) Holiday_home
The entire place is yours • 84 m² size • Kitchen
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Private Single Family Home Close to Both Water and Downtown! Best Price Match
9.5 (7 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Free WiFi
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Downtown Annapolis King George 1st Floor Hideaway Best Price Match
8.6 (7 Reviews) Apartment
The entire place is yours • Kitchen • Washing machine
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King George Downtown Annapolis Getaway Best Price Match
8.9 (9 Reviews) Apartment
The entire place is yours • 88 m² size • Kitchen
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Gaia House Best Price Match
9.3 (56 Reviews) Villa
The entire place is yours • Free on-site parking • Pets allowed
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Spectacular Location Two Bedroom State Circle Apartment Best Price Match
8.8 (12 Reviews) Apartment
The entire place is yours • 74 m² size • Private parking
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Annapolis Vacation Home 2 Mi to Quiet Waters Park Best Price Match
9.1 (16 Reviews) Holiday_home
The entire place is yours • 177 m² size • Kitchen
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Annapolis Escape Steps to Harbor backs to Gate 1 Best Price Match
9.8 (9 Reviews) Holiday_home
The entire place is yours • 56 m² size • Free on-site parking
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Walk to the stadium, downtown, West St - close to everything Best Price Match
9.6 (8 Reviews) Holiday_home
The entire place is yours • 203 m² size • Free on-site parking
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Walk to Everything Historic Arts District Best Price Match
8.6 (9 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
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Fisher House - Downtown Annapolis! Best Price Match
9.0 (6 Reviews) Holiday_home
The entire place is yours • 1000 m² size • Pet friendly
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Downtown Annapolis King George 3rd Floor Hideaway Best Price Match
8.7 (7 Reviews) Apartment
The entire place is yours • 65 m² size • Kitchen
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Oasis by the Bay - Waterfront Heated Pool Hot Tub Best Price Match
10.0 (3 Reviews) Holiday_home
The entire place is yours • 520 m² size • Free on-site parking
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Stylish + fresh bungalow 2 blocks from N-MC Stadium Best Price Match
7.6 (10 Reviews) Holiday_home
The entire place is yours • 111 m² size • Free on-site parking
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Historic Row Home 1 Block from Gate 1 at USNA Best Price Match
9.5 (4 Reviews) Holiday_home
The entire place is yours • 186 m² size • Hot tub
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* Midcentury Modern Getaway * Prime Location * Best Price Match
9.8 (4 Reviews) Holiday_home
The entire place is yours • 107 m² size • Balcony
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Annapolis @Gate 1 steps to the Harbor Free parking Best Price Match
9.2 (4 Reviews) Holiday_home
The entire place is yours • 60 m² size • Kitchen
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USNA Home In Downtown Annapolis Best Price Match
7.0 (3 Reviews) Apartment
The entire place is yours • 1000 m² size • Free on-site parking
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Sailboat Experience in Annapolis Best Price Match
8.8 (5 Reviews) Boat
Outdoor swimming pool • Pet friendly • Free WiFi
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Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! Best Price Match
9.6 (10 Reviews) Villa
The entire place is yours • 125 m² size • Free on-site parking
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Entire Private 2 bedrooms house, nice neighborhood Best Price Match
8.9 (14 Reviews) Apartment
The entire place is yours • 111 m² size • Kitchen
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Neptune By The Water Best Price Match
10.0 (8 Reviews) Holiday_home
The entire place is yours • 1000 m² size • Free on-site parking
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Pet-Friendly Beach Getaway, Relax by the Bay! Best Price Match
10.0 (6 Reviews) Apartment
The entire place is yours • 188 m² size • Free on-site parking
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Waterfront Annapolis Home Fire Pit and Fishing Pier Best Price Match
9.4 (6 Reviews) Holiday_home
The entire place is yours • 130 m² size • Private parking
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London Towne Bungalow Wloft - Walk To The Beach! Best Price Match
10.0 (4 Reviews) Holiday_home
The entire place is yours • 94 m² size • Free on-site parking
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Londontowne Hideaway Best Price Match
9.3 (4 Reviews) Holiday_home
The entire place is yours • 154 m² size • Free on-site parking
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Edgewatermayo Getaway! Best Price Match
7.4 (5 Reviews) Holiday_home
The entire place is yours • 1000 m² size • Free on-site parking
Best Price Match About Annapolis Vacation Rentals on NearbyHoliday
Looking for vacation rentals in Annapolis? Compare top options in Maryland.
Find a Vacation Rental and Holiday Home in Annapolis. Compare 31 family vacation homes, private villas, cottages, cabins, and condos in Annapolis.
NearbyHoliday makes it easy to discover vacation rentals in Annapolis that work well for families, groups, and longer stays when you want more room than a standard hotel setup.
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