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Holiday hires in Annapolis

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Annapolis, United States
1 May — 2 May2
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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 February ($549). Conversely, the most expensive month to stay in Annapolis is September ($1,179).

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

The cheapest day to stay in Annapolis is Monday ($540). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,176.

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 $319 per night.
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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 24 April 2025. The average price for a hotel in Annapolis is $552/night.
Show all 553 stays
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince George Street, Annapolis, MD, United States
0.5 km from city centre
Free Wi-Fi
$824
Avg. per night
View Deal
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Drive, Annapolis, MD, United States
4.9 km from city centre
Free Wi-Fi
$155
Avg. per night
View Deal
Inn At Horn Point
Inn At Horn Point

Inn At Horn Point

534 Burnside Street, Annapolis, MD, United States
1.5 km from city centre
Free Wi-Fi
Air conditioning
$443
Avg. per night
View Deal
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
$146
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
$149
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
$498
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 24 April 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 24 April 2025.

  • How much does a holiday rental in Annapolis cost?

    $553 per night is how much a holiday rental in Annapolis costs, on average. $66 per night was the cheapest price recently found by our users, though anything for $520 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 April, and the cheapest time to book is March.

  • 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 Red Roof Inn Annapolis as it’s currently the most popular Inn rental among our users.

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