Holiday rentals in Annapolis
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Travel insights for holiday rentals in Annapolis
Use these up-to-date, data-driven insights about booking a holiday rental in Annapolis including ideal times to book, pricing trends, and more.
What is the cheapest month to book a vacation rental in Annapolis?
The cheapest month to book a vacation rental in Annapolis is June ($583). Conversely, the most expensive month to stay in Annapolis is August ($1,652).
What is the cheapest day to stay in a vacation rental in Annapolis?
The cheapest day to stay in Annapolis is Monday ($608). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $1,554.
How far ahead should you book a vacation rental in Annapolis?
Save money by booking a vacation rental at least 66 days before your trip to Annapolis. The lowest price found when booking 66 days ahead was $339 per night.
Other accommodations in Annapolis
Find the perfect holiday rental for your stay in Annapolis. There are 553 hotels in Annapolis and price data was last updated on 8 June 2025. The average price for a hotel in Annapolis is $593/night.
Show all 553 stays
210 Holiday Court, Annapolis, MD, United States
4.8 km from city centre
Free Wi-Fi
Parking
$224
Avg. per night
134 Prince George Street, Annapolis, MD, United States
0.5 km from city centre
Free Wi-Fi
$832
Avg. per night
124 Womack Drive, Annapolis, MD, United States
4.9 km from city centre
Free Wi-Fi
$175
Avg. per night
2520C Riva Road, Annapolis, MD, United States
4.8 km from city centre
Free Wi-Fi
Air conditioning
$155
Avg. per night
69 Old Mill Bottom Road, Annapolis, MD, United States
5.2 km from city centre
Free Wi-Fi
Air conditioning
$171
Avg. per night
26 Randall Street, Annapolis, MD, United States
0.5 km from city centre
Free Wi-Fi
Air conditioning
$528
Avg. per night