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Holiday rentals in Annapolis

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Travel insights for holiday rentals in Annapolis

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Annapolis.

What is the cheapest month to book a vacation rental in Annapolis?

The cheapest month to book a vacation rental in Annapolis is November (£73). Conversely, the most expensive month to stay in Annapolis is July (£353).

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

The cheapest day to stay in Annapolis is Tuesday (£140). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is £281.

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 £155 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 27 June 2025. The average price for a hotel in Annapolis is £280/night.
Red Roof Inn Annapolis
Red Roof Inn Annapolis

Red Roof Inn Annapolis

2520C Riva Road, Annapolis, MD, United States
3.0 mi from city centre
Free Wi-Fi
Air conditioning
£68
Avg. per night
View Deal
Village Inn
Village Inn

Village Inn

69 Old Mill Bottom Road, Annapolis, MD, United States
3.2 mi from city centre
Free Wi-Fi
Air conditioning
£74
Avg. per night
View Deal
Flag House Inn
Flag House Inn

Flag House Inn

26 Randall Street, Annapolis, MD, United States
0.3 mi from city centre
Free Wi-Fi
Air conditioning
£203
Avg. per night
View Deal
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

174 West Street, Annapolis, MD, United States
0.4 mi from city centre
Free Wi-Fi
£90
Avg. per night
View Deal
The Westin Annapolis
The Westin Annapolis

The Westin Annapolis

100 Westgate Circle, Annapolis, MD, United States
0.7 mi from city centre
Pool
Free Wi-Fi
£144
Avg. per night
View Deal
Historic Inns of Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle, Annapolis, MD, United States
0.1 mi from city centre
Free Wi-Fi
£119
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 27 June 2025.
Whether you're visiting Annapolis for leisure or business, utilise the map to find holiday rentals close to your ideal location. You can find more information on a particular holiday 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 27 June 2025.

  • How much does a holiday rental in Annapolis cost?

    Annapolis holiday rentals are £280/night on average. However, you may find that prices fluctuate depending on the time of year. For example, October is the most expensive month to book a holiday rental in Annapolis, and March is often the cheapest month to book. Recently, our users found rentals for £31/night - which is currently the cheapest price. Keep in mind that anything £256/night or less is still considered a good deal.

  • What part of Annapolis is best to stay in?

    Consider staying in Downtown when looking for Annapolis holiday rentals. Downtown is the most popular neighbourhood in the city according to our users. In fact, out of all users who looked for holiday rentals in Annapolis in the past year, 96% of them searched for rentals in Downtown. If it’s available, we recommend staying at the Cozy 2br home w/ parking in downtown Annapolis, a HotelsCombined favourite when it comes to holiday rentals in Annapolis’s Downtown neighbourhood.

  • 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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