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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 (€128). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is €455.
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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 €67 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 9 December 2025
Out of the holiday rentals in Annapolis we've come across, these properties are priced the lowest. As prices can vary by date, change the dates if you're flexible to compare rates.
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
€67
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 400 hotels in Annapolis and price data was last updated on 9 December 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
4.8 km from city centre
Free Wi-Fi
Air conditioning
€60
Avg. per night
View Deal
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
€74
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
€179
Avg. per night
View Deal
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
€132
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 9 December 2025.
Utilise the map to find properties close to the Annapolis area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular 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 9 December 2025.

  • How much does a holiday rental in Annapolis cost?

    The average cost for a holiday rental in Annapolis is €310/night. A good holiday rental deal in Annapolis would be for €270/night or less. The cheapest rental deal found recently by our users was €36/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?

    There are 2 holiday rentals in Annapolis that fall under the Inn category, the most popular is Village Inn.

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