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Holiday hires 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 ($499). Conversely, the most expensive month to stay in Annapolis is August ($1,413).

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

The cheapest day to stay in Annapolis is Monday ($520). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $1,329.
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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 6 June 2025. The average price for a hotel in Annapolis is $548/night.
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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
$143
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
$158
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
$489
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 6 June 2025.
Navigate to the areas in Annapolis you plan to visit to find holiday rentals that are close by. Users can click on a holiday rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 6 June 2025.

  • How much does a holiday rental in Annapolis cost?

    $549 per night is how much a holiday rental in Annapolis costs, on average. $60 per night was the cheapest price recently found by our users, though anything for $523 per night or less is a good deal. Keep in mind that Annapolis holiday rental prices fluctuate throughout the year: the most expensive month to book is May, and the cheapest time to book is May.

  • Are there any Inn holiday rentals in Annapolis?

    If you’re looking to book a Inn holiday rental in Annapolis, then you have 2 to choose from. We recommend looking at Village Inn as it’s currently the most popular Inn rental among our users.

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