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Search results; Over 1,000 homes in Annapolis

Top guest favorite
Water views and a hot tub greet you at this Annapolis house with a fire pit
4 bedrooms, 4 beds, 2.5 private baths
Sep 13 – 18
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4.99 out of 5 average rating, 140 reviews
Guest favorite
Private room
This 1926 Four Square home in Homewood gives you a fire pit and covered porch
4.95 out of 5 average rating, 186 reviews, 1 queen bed, 3 baths
Sep 20 – 25
Top guest favorite
Exposed brick and metallic textures greet you at this industrial-chic Annapolis loft
4.92 out of 5 average rating, 1132 reviews, 1 bedroom, 2 beds, 1 bath
Nov 1 – 6
Guest favorite
Private room
This 1926 Homewood home gives you a covered porch, fire pit, and mature gardens
4.93 out of 5 average rating, 190 reviews, 1 queen bed, 1.5 baths
Aug 16 – 21
Guest favorite
Private room
Look out over Lake Hillsmere from your private rooftop patio at this treetop suite
4.96 out of 5 average rating, 134 reviews, 1 queen bed, 1 bath
Aug 16 – 21
Top guest favorite
This newly renovated Eastport condo gives you rooftop views of downtown Annapolis
4.96 out of 5 average rating, 168 reviews, 2 beds, 1 bath
Aug 23 – 28
Top guest favorite
Private room
This Cape Cod home in St Margarets gives you a saltwater pool and hot tub
4.94 out of 5 average rating, 358 reviews, 1 king bed, 1 bath
Aug 17 – 22
Top guest favorite
Private room
This Baltimore room puts you 2 blocks from the Chesapeake with a private garden
5.0 out of 5 average rating, 33 reviews, 1 queen bed, 1 bath
Aug 16 – 21
Top guest favorite
This bright Annapolis apartment puts you one block from Main St with a screened porch
4.93 out of 5 average rating, 85 reviews, 2 bedrooms, 1 bed, 1.5 baths
Aug 23 – 28
Guest favorite
This 33-foot sailboat in Annapolis puts you among ospreys and open water
4.93 out of 5 average rating, 60 reviews, 1 bedroom, 2 beds, Half-bath
Aug 17 – 22
Top guest favorite
This Annapolis-area suite gives you a spa-like shower and seasonal pool
4.94 out of 5 average rating, 219 reviews, 1 bedroom, 2 beds, 1 bath
Aug 13 – 18
Top guest favorite
Private room
This renovated Historic District townhouse puts you on a tree-lined Annapolis street
4.97 out of 5 average rating, 258 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 17 – 22
Top guest favorite
This South River waterfront cottage gives you a fire pit, grill, and pool
5.0 out of 5 average rating, 222 reviews, 1 bedroom, 1 bed, 1 bath
Oct 17 – 22
Top guest favorite
This Baltimore cottage gives you a fireplace, fire pit, and patio for quiet evenings
4.96 out of 5 average rating, 78 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Top guest favorite
Look out over Mill Creek from this eclectic wooded cottage near Annapolis
4.97 out of 5 average rating, 469 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Cathedral ceilings and full-length windows greet you at this Murray Hill studio
4.97 out of 5 average rating, 457 reviews, 1 bedroom, 2 beds, 1 bath
Nov 29 – Dec 4
Top guest favorite
French doors open to a pool and hammocks at this forested Annapolis suite
4.95 out of 5 average rating, 142 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 9 – 15
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
4.59 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bath
Aug 13 – 18
Top guest favorite
This boho mid-century Annapolis house gives you a fenced yard, deck, and fire pit
5.0 out of 5 average rating, 37 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 28 – Oct 3