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Holiday 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 day to stay in a vacation rental in Annapolis?

The cheapest day to stay in Annapolis is Friday ($254). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $921.

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Cheapest holiday 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 $140 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 22 January 2026
These Annapolis properties charge the lowest price per night of those we've come across. If you have the flexibility, change the dates selected to compare prices.
Candlewood Suites Annapolis By IHG
Candlewood Suites Annapolis By IHG

Candlewood Suites Annapolis By IHG

1 South Womack Drive, Annapolis, MD, United States
4.7 km from city centre
Free Wi-Fi
Parking
$140
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 380 hotels in Annapolis and price data was last updated on 22 January 2026. The average price for a hotel in Annapolis is .
The Westin Annapolis
The Westin Annapolis

The Westin Annapolis

100 Westgate Circle, Annapolis, MD, United States
1.1 km from city centre
Pool
Free Wi-Fi
$200
Avg. per night
View Deal
Historic Inns of Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle, Annapolis, MD, United States
0.2 km from city centre
Free Wi-Fi
$192
Avg. per night
View Deal
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
$120
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
$329
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 22 January 2026.
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 holiday rental they're interesting in to find helpful information and deals for that holiday 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 22 January 2026.

  • How much does a holiday rental in Annapolis cost?

    $551/night is a typical cost for a holiday rental in Annapolis throughout the year. Rental prices do vary though, and you’ll find that October is the most expensive month to book, and August is the cheapest month to book. HotelsCombined users recently found Annapolis holiday rentals for as low as $72/night. In general, any Annapolis rental for $470 or less is a good deal.

  • What part of Annapolis is best to stay in?

    Downtown is the most popular area of Annapolis to stay in. In the past year, 98% of HotelsCombined users looking for Annapolis holiday rentals searched within Downtown. Based on user data, the Cozy 2br home w/ parking in downtown Annapolis is one of the most popular holiday rentals in Downtown.

  • Are there any Inn holiday rentals in Annapolis?

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

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