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Holiday rentals in Annapolis

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Travel insights for holiday rentals in Annapolis

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Annapolis.

What is the cheapest day to stay in a vacation rental in Annapolis?

The cheapest day to stay in Annapolis is Monday ($420). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,934.

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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 $171 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 July 2026
These Annapolis properties charge the lowest price per night of those we've come across. If you have the flexibility, change the dates selected to compare prices.
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
$171
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 412 hotels in Annapolis and price data was last updated on 23 July 2026. The average price for a hotel in Annapolis is .
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
$416
Avg. per night
View Deal
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince George Street, Annapolis, MD, United States
0.5 km from city centre
Free Wi-Fi
$420
Avg. per night
View Deal
Crowne Plaza Annapolis By IHG
Crowne Plaza Annapolis By IHG

Crowne Plaza Annapolis By IHG

173 Jennifer Road, Annapolis, MD, United States
4.5 km from city centre
Pool
Free Wi-Fi
Parking
$199
Avg. per night
View Deal
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Drive, Annapolis, MD, United States
4.9 km from city centre
Free Wi-Fi
$188
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 July 2026.
Scroll to and zoom in on the areas in Annapolis you plan on visiting to find nearby properties. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that 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 23 July 2026.

  • How much does a holiday rental in Annapolis cost?

    $691/night is a typical cost for a holiday rental in Annapolis throughout the year. Rental prices do vary though, and you’ll find that April is the most expensive month to book, and January is the cheapest month to book. HotelsCombined users recently found Annapolis holiday rentals for as low as $73/night. In general, any Annapolis rental for $624 or less is a good deal.

  • Are there any Motel holiday rentals in Annapolis?

    At the moment, there are 3 properties listed as a Motel holiday rental in Annapolis. A popular Motel in Annapolis amongst our users is Village Inn Annapolis MD.

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