Vacation rentals in Annapolis

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Popular amenities for Annapolis vacation rentals

Stay near Annapolis's top sights

Annapolis City Dock34 locals recommend
Navy-Marine Corps Memorial Stadium34 locals recommend
Graduate Annapolis11 locals recommend
Maryland State House81 locals recommend
Historic Inns of Annapolis8 locals recommend
Rams Head On Stage22 locals recommend

Other great vacation rentals in Annapolis

Guest favourite

Guest suite in Annapolis

4.97 out of 5 average rating, 163 reviews

Private 2B Apt--less than 1 mi to Downtown

Oct. 27 – Nov. 3

$246 CAD per night
Guest favourite

Guest suite in Annapolis

4.97 out of 5 average rating, 115 reviews

Great reviews! Pool, DT, stadium, goats, and more!

Nov. 21 – 28

$261 CAD per night
Guest favourite

Guest suite in Edgewater

4.89 out of 5 average rating, 437 reviews

South River Park Apartment

Jul. 30 – Aug. 6

$153 CAD per night
Guest favourite

Guest suite in Arnold

4.85 out of 5 average rating, 497 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

Jul. 11 – 18

$181 CAD per night
Guest favourite

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

Apr. 13 – 20

$618 CAD per night
Guest favourite

Condo in Annapolis

4.96 out of 5 average rating, 147 reviews

The Crow's Nest - Excellent downtown Annapolis Apt

Jul. 10 – 17

$326 CAD per night
Guest favourite

Boat in Annapolis

4.94 out of 5 average rating, 351 reviews

Stay aboard the S/V MY STUDIO on Annapolis Harbor

Nov. 30 – Dec. 7

$317 CAD per night
Guest favourite

Condo in Annapolis

4.96 out of 5 average rating, 54 reviews

Funky Uptown Apt meets Downtown - Hist District

May 28 – Jun. 4

$249 CAD per night

Quick stats about vacation rentals in Annapolis

  • Total rentals

    640 properties

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

  • Rentals with a pool

    40 properties have a pool

  • Pet-friendly rentals

    180 properties allow pets

  • Family-friendly rentals

    440 properties are a good fit for families

  • Total number of reviews

    28K reviews

Destinations to explore