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Vacation rentals in Annapolis

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Annapolis, United States
Apr 29 — Apr 302
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Travel insights for vacation rentals in Annapolis

Use our HotelsCombined data-powered tips to help you find your next vacation 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 February ($224). Conversely, the most expensive month to stay in Annapolis is September ($481).

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 Tuesday, when the average nightly price is $479.

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 vacation rental for your stay in Annapolis. There are 552 hotels in Annapolis and price data was last updated on April 22, 2025. The average price for a hotel in Annapolis is $352/night.
Show all 552 stays
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
$93
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
$95
Avg. per night
View Deal
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court, Annapolis, MD, United States
3.0 mi from city centre
Free Wi-Fi
Parking
$126
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
0.3 mi from city centre
Free Wi-Fi
$526
Avg. per night
View Deal
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Drive, Annapolis, MD, United States
3.0 mi from city centre
Free Wi-Fi
$99
Avg. per night
View Deal

Where to stay in Annapolis

Explore different neighborhoods and areas within Annapolis to find the perfect location for your stay. Map data was last updated on April 22, 2025.
Scroll to and zoom in on the areas in Annapolis you plan on visiting to find nearby properties. As an added benefit, users can click a vacation rental they're interesting in to find helpful information and deals for that 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 April 22, 2025.

  • How much does a vacation rental in Annapolis cost?

    $353 per night is how much a vacation rental in Annapolis costs, on average. $42 per night was the cheapest price recently found by our users, though anything for $332 per night or less is a good deal. Keep in mind that Annapolis vacation rental prices fluctuate throughout the year: the most expensive month to book is April, and the cheapest time to book is March.

  • What part of Annapolis is best to stay in?

    The best neighborhood to stay in Annapolis is Downtown, according to our user data. 21% of our users who looked for vacation rentals in Annapolis searched for properties in the Downtown area. If you’re also interested in booking a vacation rental in Downtown, consider the Cozy 2br home w/ parking in downtown Annapolis - the neighborhood’s most popular rental property.

  • Are there any Inn vacation rentals in Annapolis?

    At the moment, there are 2 properties listed as a Inn vacation rental in Annapolis. A popular Inn in Annapolis amongst our users is Red Roof Inn Annapolis.

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