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Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Entire apartment
  2. Annapolis
The Crow's Nest - Excellent downtown Annapolis Apt

Convenient and cozy, self check-in apartment in downtown Annapolis. Steps away from the Naval Academy and Main Street. The perfect place for a getaway to explore the city, visit USNA, or stay for business.

$228 SGD per night
SUPERHOST
  1. Entire apartment
  2. Annapolis
New Downtown Annapolis Condo With Free Parking

This newly constructed property brings chic, low-maintenance living to the heart of West Street in Annapolis. Boutique condos that display style and class atop the charm of the Arts District. No parties, events, or large gatherings are permitted at any time during the stay! Airbnb provides damage protection for broken items and property damage! A week-long stay discount is 20%! A month-long stay discount is 30%! Pets are only $75 per stay! Additional guests are $15 per person per night

$245 SGD per night
SUPERHOST
  1. Entire apartment
  2. Annapolis
Annapolis Waterfront Condo - Unit #: A-203

Experience the quiet beauty of Eastport. Fifteen minute walk to downtown Annapolis and USNA. Free parking options, can accommodate a trailer. One bedroom apartment with queen bed, one bath, living room has a queen sleeper sofa and fire place, full kitchen, and protected spacious deck overlooking Spa Creek and Annapolis. Condo is completely non-smoking. Keurig. Washer/dryer. Grilling area. Pool - Memorial to Labor Day, ONLY. Pool Hours Weekdays 4pm - 8, Holidays and weekends 11-8.

$222 SGD per night

Holiday rentals for every style

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Stay near Annapolis's top sights

Photo of Annapolis City Dock
Annapolis City Dock15 locals recommend
Photo of United States Naval Academy
United States Naval Academy49 locals recommend
Photo of US Naval Academy Museum
US Naval Academy Museum15 locals recommend
Photo of Downtown Annapolis Partnership
Downtown Annapolis Partnership10 locals recommend
Photo of Truxtun Park
Truxtun Park10 locals recommend
Photo of Jonas Park
Jonas Park5 locals recommend

Other great holiday rentals in Annapolis

  1. Private room
  2. Annapolis
Single room
$60 SGD per night
PLUS
  1. Entire loft
  2. Annapolis
Step Out to Main Street From a Chic Loft
$234 SGD per night
PLUS
  1. Entire rental unit
  2. Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
$295 SGD per night
  1. Private room
  2. Annapolis
Howard's Cove Retreat
$101 SGD per night
  1. Entire townhouse
  2. Annapolis
Beautiful Townhome Downtown Annapolis
$229 SGD per night
SUPERHOST
  1. Private room
  2. Annapolis
Annapolis 1 bedroom quest suite
$89 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Annapolis
Private Annapolis Inlaw Apartment
$132 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Annapolis
Modern Apartment over the Heart of Main Street!
$192 SGD per night
SUPERHOST
  1. Entire apartment
  2. Annapolis
Beautiful Condo By The Navy Academy
$210 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Annapolis
Charming Eastport
$223 SGD per night
SUPERHOST
  1. Entire home
  2. Annapolis
New Hotel Chic
$335 SGD per night
  1. Private room
  2. Annapolis
Chesapeake Mornings
$86 SGD per night