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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 (S$ 192). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is S$ 671.
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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 S$ 113 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 November 2025
Out of the vacation rentals in Annapolis we've come across, these properties are priced the lowest. 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 South Womack Drive, Annapolis, MD, United States
4.7 km from city centre
Free Wi-Fi
Parking
S$ 113
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 401 hotels in Annapolis and price data was last updated on 14 November 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
S$ 235
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
S$ 133
Avg. per night
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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$ 87
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 November 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 14 November 2025.

  • How much does a holiday rental in Annapolis cost?

    On average, it costs S$ 432 per night for a Annapolis holiday rental, but S$ 393 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$ 55 per night. If you can, try to avoid booking your rental October (as this is the most expensive month). Booking April (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.

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