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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 February ($224). Conversely, the most expensive month to stay in Annapolis is September ($548).

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

The cheapest day to stay in Annapolis is Monday ($220). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $451.

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 $204 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 1 May 2025. The average price for a hotel in Annapolis is $358/night.
Show all 553 stays
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
$93
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
$95
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
$318
Avg. per night
View Deal
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
$514
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
$99
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
$283
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 1 May 2025.
Utilize the map to find properties close to the Annapolis area(s) or attractions you plan on visiting. You can find more information on a particular vacation rental within the map by clicking on its name.

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 1 May 2025.

  • How much does a holiday rental in Annapolis cost?

    The average cost for a holiday rental in Annapolis is $358/night. A good holiday rental deal in Annapolis would be for $334/night or less. The cheapest rental deal found recently by our users was $42/night. If you’re flexible with your travel dates, then try to avoid booking September, the most expensive month of the year. Booking March is the cheapest month to book a holiday rental in Annapolis.

  • Are there any Inn holiday rentals in Annapolis?

    Yes, there are 2 Inn holiday rentals in Annapolis. According to our data, Red Roof Inn Annapolis is currently the most popular Inn rental in the city.

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