Insights
Cheapest hotels
Where to stay

Holiday rentals in Annapolis

Search and compare Annapolis, MD holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

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 Tuesday ($326). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $871.

Find deals

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 $160 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 9 June 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
$160
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 431 hotels in Annapolis and price data was last updated on 9 June 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
$446
Avg. per night
View Deal
DoubleTree by Hilton Annapolis
DoubleTree by Hilton Annapolis

DoubleTree by Hilton Annapolis

210 Holiday Court, Annapolis, MD, United States
4.8 km from city centre
Free Wi-Fi
Parking
$191
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
$463
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
$198
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 9 June 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 9 June 2026.

  • How much does a holiday rental in Annapolis cost?

    $604/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 November 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 $531 or less is a good deal.

  • What part of Annapolis is best to stay in?

    Downtown is the most popular area of Annapolis to stay in. In the past year, 99% of HotelsCombined users looking for Annapolis holiday rentals searched within Downtown. Based on user data, the Governor Calvert 2 Double Beds | Historic Inns | Near Naval Academy is one of the most popular holiday rentals in Downtown.

  • Are there any Inn holiday rentals in Annapolis?

    At the moment, there are 2 properties listed as a Inn holiday rental in Annapolis. A popular Inn in Annapolis amongst our users is Village Inn Annapolis MD.

Find better results for your stay in Annapolis