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Vacation 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 ($149). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $538.

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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 $78 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 14 December 2025
Currently, these are the lowest-priced vacation rentals in Annapolis we've come across for the dates selected. 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 South Womack Drive, Annapolis, MD, United States
4.7 km from city centre
Free Wi-Fi
Parking
$78
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 398 hotels in Annapolis and price data was last updated on 14 December 2025. 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
$150
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
$112
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
$72
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
$208
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 14 December 2025.
Utilize the map to find properties close to the Annapolis area(s) or attractions you plan on visiting. You can find more information on a particular vacation 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 14 December 2025.

  • How much does a holiday rental in Annapolis cost?

    The average cost for a holiday rental in Annapolis is $357/night. A good holiday rental deal in Annapolis would be for $309/night or less. The cheapest rental deal found recently by our users was $42/night. If you’re flexible with your travel dates, then try to avoid booking October, the most expensive month of the year. Booking June is the cheapest month to book a holiday rental in Annapolis.

  • Are there any Inn holiday rentals in Annapolis?

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

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