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Vacation rentals in Annapolis

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Travel insights for vacation rentals in Annapolis

Use these up-to-date, data-driven insights about booking a vacation 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 Monday (C$ 270). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is C$ 620.
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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 C$ 125 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 23 October 2025
These Annapolis properties charge the lowest price per night of those we've come across. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
Candlewood Suites Annapolis By IHG
Candlewood Suites Annapolis By IHG

Candlewood Suites Annapolis By IHG

1 Womack Drive, Annapolis, MD, United States
4.7 km from city centre
Free Wi-Fi
Parking
C$ 125
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect vacation rental for your stay in Annapolis. There are 422 hotels in Annapolis and price data was last updated on 23 October 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
C$ 105
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
C$ 122
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
C$ 375
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
C$ 244
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
C$ 148
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 23 October 2025.
Use the map to find vacation rentals in Annapolis that are close to the points of interest you'll be frequenting. Clicking a property's name will unlock more information and allow you to book that particular 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 23 October 2025.

  • How much does a vacation rental in Annapolis cost?

    Annapolis vacation rentals are C$ 461/night on average. However, you may find that prices fluctuate depending on the time of year. For example, October is the most expensive month to book a vacation rental in Annapolis, and April is often the cheapest month to book. Recently, our users found rentals for C$ 59/night - which is currently the cheapest price. Keep in mind that anything C$ 420/night or less is still considered a good deal.

  • What part of Annapolis is best to stay in?

    Downtown is the best part of Annapolis to stay in based on our user data. Out of all our users who looked at Annapolis vacation rentals, 99% of them looked for stays in the Downtown neighbourhood in the last year. The 18th Cent. Charm in Historic Downtown Annapolis happens to be the most popular vacation rental in the Downtown neighbourhood of Annapolis.

  • Are there any Inn vacation rentals in Annapolis?

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

Find better results for your stay in Annapolis

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