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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 Thursday (S$ 434). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is S$ 884.

How far ahead should you book a vacation rental in Annapolis?

Save money by booking a vacation rental at least 76 days before your trip to Annapolis. The lowest price found when booking 76 days ahead was S$ 301 per night.
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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$ 128 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 15 September 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 Womack Drive, Annapolis, MD, United States
4.7 km from city centre
Free Wi-Fi
Parking
S$ 128
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 651 hotels in Annapolis and price data was last updated on 15 September 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$ 288
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$ 140
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
S$ 100
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
S$ 122
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 15 September 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 15 September 2025.

  • How much does a holiday rental in Annapolis cost?

    On average, it costs S$ 430 per night for a Annapolis holiday rental, but S$ 362 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 September (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

Consider other places to stay in Annapolis

Stay at one of these places that users have found on HotelsCombined.
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