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Vacation 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 November (S$ 222). Conversely, the most expensive month to stay in Annapolis is July (S$ 1,293).

What is the cheapest day to stay in a vacation rental in Annapolis?

The cheapest day to stay in Annapolis is Tuesday (S$ 429). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 1,314.

How far ahead should you book a vacation rental in Annapolis?

Save money by booking a vacation rental at least 65 days before your trip to Annapolis. The lowest price found when booking 65 days ahead was S$ 271 per night.
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Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 554 hotels in Annapolis and price data was last updated on 5 July 2025. The average price for a hotel in Annapolis is S$ 463/night.
Red Roof Inn Annapolis
Red Roof Inn Annapolis

Red Roof Inn Annapolis

2520C Riva Road, Annapolis, MD, United States
4.8 km from city centre
Free Wi-Fi
Air conditioning
S$ 118
Avg. per night
View Deal
Village Inn
Village Inn

Village Inn

69 Old Mill Bottom Road, Annapolis, MD, United States
5.2 km from city centre
Free Wi-Fi
Air conditioning
S$ 125
Avg. per night
View Deal
Flag House Inn
Flag House Inn

Flag House Inn

26 Randall Street, Annapolis, MD, United States
0.5 km from city centre
Free Wi-Fi
Air conditioning
S$ 316
Avg. per night
View Deal

Where to stay in Annapolis

Explore different neighbourhoods and areas within Annapolis to find the perfect location for your stay. Map data was last updated on 5 July 2025.
Utilize the map to find properties close to the Annapolis area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular vacation rental.

Facts about staying in Annapolis

Find useful tips and insights about staying in Annapolis to help you make the most of your experience. FAQs were last updated on 5 July 2025.

  • How much does a holiday rental in Annapolis cost?

    On average, it costs S$ 463 per night for a Annapolis holiday rental, but S$ 441 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Annapolis was for S$ 54 per night. If you can, try to avoid booking your rental October (as this is the most expensive month). Booking March (the cheapest month) may end up saving you money.

  • Are there any Inn holiday rentals in Annapolis?

    There are 2 holiday rentals in Annapolis that fall under the Inn category, the most popular is Village Inn.

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