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Holiday hires 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 ($297). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $681.
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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 $137 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 24 October 2025
Out of the holiday 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 holiday rental, and holiday 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
$137
Avg. per night
View Deal

Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 422 hotels in Annapolis and price data was last updated on 24 October 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
$115
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
$134
Avg. per night
View Deal
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
$412
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 24 October 2025.
Navigate to the areas in Annapolis you plan to visit to find holiday rentals that are close by. Users can click on a holiday rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 24 October 2025.

  • How much does a holiday rental in Annapolis cost?

    $506 per night is how much a holiday rental in Annapolis costs, on average. $65 per night was the cheapest price recently found by our users, though anything for $461 per night or less is a good deal. Keep in mind that Annapolis holiday rental prices fluctuate throughout the year: the most expensive month to book is October, and the cheapest time to book is April.

  • What is the best Annapolis holiday rental?

    The best holiday rental in Annapolis is Candlewood Suites Annapolis By IHG, according to our user data. 677 users from HotelsCombined gave the Candlewood Suites Annapolis By IHG a 7.4/10 rating.

  • Are there any Inn holiday rentals in Annapolis?

    If you’re looking to book a Inn holiday rental in Annapolis, then you have 2 to choose from. We recommend looking at Village Inn as it’s currently the most popular Inn rental among our users.

Find better results for your stay in Annapolis

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $77 and Hotels Under $154. Discover hotel discounts now and make your hotel reservation today.