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Vacation rentals in Annapolis

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Travel insights for vacation rentals in Annapolis

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 394). Conversely, the most expensive month to stay in Annapolis is August (C$ 1,117).

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

The cheapest day to stay in Annapolis is Monday (C$ 411). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is C$ 1,051.
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Other accommodations in Annapolis

Find the perfect vacation rental for your stay in Annapolis. There are 550 hotels in Annapolis and price data was last updated on 5 June 2025. The average price for a hotel in Annapolis is C$ 488/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
C$ 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
C$ 141
Avg. per night
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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
C$ 435
Avg. per night
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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 5 June 2025.
Use the map to find vacation rentals in Annapolis that are close to the points of interest you'll be frequenting. Clicking a property's name will unlock more information and allow you to book that particular vacation 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 5 June 2025.

  • How much does a vacation rental in Annapolis cost?

    Annapolis vacation rentals are C$ 488/night on average. However, you may find that prices fluctuate depending on the time of year. For example, May is the most expensive month to book a vacation rental in Annapolis, and May is often the cheapest month to book. Recently, our users found rentals for C$ 54/night - which is currently the cheapest price. Keep in mind that anything C$ 465/night or less is still considered a good deal.

  • What part of Annapolis is best to stay in?

    Downtown is the best part of Annapolis to stay in based on our user data. Out of all our users who looked at Annapolis vacation rentals, 90% of them looked for stays in the Downtown neighbourhood in the last year. The Cozy 2br home w/ parking in downtown Annapolis happens to be the most popular vacation rental in the Downtown neighbourhood of Annapolis.

  • Are there any Inn vacation rentals in Annapolis?

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

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