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Vacation rentals in Annapolis

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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 day to stay in a vacation rental in Annapolis?

The cheapest day to stay in Annapolis is Thursday ($264). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $538.

How far ahead should you book a vacation rental in Annapolis?

Save money by booking a vacation rental at least 76 days before your trip to Annapolis. The lowest price found when booking 76 days ahead was $235 per night.
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Cheapest vacation rentals in Annapolis, Maryland

Discover affordable stays in Annapolis that provide a quality experience without breaking the bank. Hotels in Annapolis can be found for as low as $100 per night. There is currently one property in Annapolis that can be booked for this price. Candlewood Suites Annapolis By IHG is one of the hotels that can be booked for the lowest price in Annapolis. Price data was last updated on syyskuu 18, 2025
These Annapolis properties charge the lowest price per night of those we've come across. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Candlewood Suites Annapolis By IHG
Candlewood Suites Annapolis By IHG

Candlewood Suites Annapolis By IHG

1 Womack Drive, Annapolis, MD, United States
2.9 mi from city centre
Free Wi-Fi
Parking
$100
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect vacation rental for your stay in Annapolis. There are 650 hotels in Annapolis and price data was last updated on syyskuu 18, 2025. The average price for a hotel in Annapolis is .
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
$78
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
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
$234
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
$225
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
$122
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 syyskuu 18, 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 syyskuu 18, 2025.

  • How much does a vacation rental in Annapolis cost?

    $350 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 $299 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 September, 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. 5% 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 Village Inn.

Find better results for your stay in Annapolis

Consider other places to stay in Annapolis

Stay at one of these places that users have found on HotelsCombined.
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Annapolis Resorts

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly, including Hotels Under $50 and Hotels Under $100. Discover hotel discounts now and make your hotel reservation today.