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 day to stay in a vacation rental in Annapolis?

The cheapest day to stay in Annapolis is Thursday ($757). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $1,534.
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Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 655 hotels in Annapolis and price data was last updated on 9 September 2025. The average price for a hotel in Annapolis is .
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
$127
Avg. per night
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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
$159
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 9 September 2025.
Scroll to and zoom in on the areas in Annapolis you plan on visiting to find nearby properties. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday 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 9 September 2025.

  • How much does a holiday rental in Annapolis cost?

    $666/night is a typical cost for a holiday rental in Annapolis throughout the year. Rental prices do vary though, and you’ll find that October is the most expensive month to book, and March is the cheapest month to book. HotelsCombined users recently found Annapolis holiday rentals for as low as $71/night. In general, any Annapolis rental for $625 or less is a good deal.

  • What part of Annapolis is best to stay in?

    Downtown is the most popular area of Annapolis to stay in. In the past year, 98% of HotelsCombined users looking for Annapolis holiday rentals searched within Downtown. Based on user data, the Cozy 2br home w/ parking in downtown Annapolis is one of the most popular holiday rentals in Downtown.

  • Are there any Inn holiday rentals in Annapolis?

    At the moment, there are 2 properties listed as a Inn holiday rental in Annapolis. A popular Inn in Annapolis amongst our users is Village Inn.

Find better results for your stay in Annapolis

Consider other places to stay in Annapolis

Stay at one of these places that users have found on HotelsCombined.
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