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 Monday (S$ 477). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is S$ 1,723.
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Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 655 hotels in Annapolis and price data was last updated on 26 August 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
S$ 112
Avg. per night
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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
S$ 124
Avg. per night
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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
S$ 255
Avg. per night
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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
S$ 291
Avg. per night
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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
S$ 212
Avg. per night
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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 26 August 2025.
Utilize 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 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 26 August 2025.

  • How much does a holiday rental in Annapolis cost?

    On average, it costs S$ 421 per night for a Annapolis holiday rental, but S$ 370 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Annapolis was for S$ 54 per night. If you can, try to avoid booking your rental August (as this is the most expensive month). Booking March (the cheapest month) may end up saving you money.

  • 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.

Find better results for your stay in Annapolis

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