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Search results; Over 1,000 homes in Annapolis

Guest favorite
Private room
A private room with its own entrance and deck in Historic Annapolis
1 bedroom, 1 bed, 1 shared bath
Aug 12 – 17
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4.84 out of 5 average rating, 478 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
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
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
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
Top guest favorite
Wake to creek views at this 1910 waterfront cottage in West Annapolis
4.98 out of 5 average rating, 163 reviews, 1 bed, 1 bath
Aug 29 – Sep 3
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
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
Guest favorite
This historic downtown Annapolis townhouse gives you a private patio and 1900s charm
4.92 out of 5 average rating, 25 reviews, 2 bedrooms, 6 beds, 2 baths
Aug 16 – 21
Top guest favorite
Sun-drenched Annapolis apartment with a huge balcony less than a block from the water
5.0 out of 5 average rating, 41 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 14 – 19
Guest favorite
This historic Annapolis house puts you a 2-minute walk from the city dock
4.95 out of 5 average rating, 78 reviews, 1 bedroom, 2 beds, 1.5 baths
Aug 12 – 17
Guest favorite
Soak in South River views from the deck of this waterfront Annapolis house
4.92 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 2.5 baths
Sep 7 – 12
Guest favorite
This Annapolis guesthouse gives you a bluestone patio, fire pit, and wooded privacy
4.95 out of 5 average rating, 210 reviews, 1 bedroom, 1 bed, 1 bath
Aug 12 – 17
This newly renovated Annapolis townhome gives you designer finishes and a fenced deck
New place to stay, 4 bedrooms, 4 beds, 3.5 baths
Aug 16 – 21
Top guest favorite
You’ll take in Chesapeake Bay Bridge views from this 43-foot Annapolis yacht
4.96 out of 5 average rating, 114 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 18 – 23
Top guest favorite
This Admiral Heights house gives you a fire pit, patio, and fireplace
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 15 – 20
Top guest favorite
Wake to Chesapeake Bay views from bed at this waterfront guesthouse with a pool
4.99 out of 5 average rating, 359 reviews, 1 bed, 1 bath
Aug 16 – 21
Top guest favorite
This restored 1928 Annapolis cottage greets you with vaulted ceilings and a brick terrace
4.93 out of 5 average rating, 227 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 12 – 17
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