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 Thursday ($613). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $1,243.
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Other accommodations in Annapolis

Find the perfect holiday rental for your stay in Annapolis. There are 655 hotels in Annapolis and price data was last updated on 9 September 2025. The average price for a hotel in Annapolis is .
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court, Annapolis, MD, United States
4.8 km from city centre
Free Wi-Fi
Parking
$198
Avg. per night
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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
$378
Avg. per night
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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
$182
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
$132
Avg. per night
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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
$144
Avg. per night
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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
$356
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 September 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 9 September 2025.

  • How much does a holiday rental in Annapolis cost?

    $599 per night is how much a holiday rental in Annapolis costs, on average. $64 per night was the cheapest price recently found by our users, though anything for $563 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 March.

  • 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 $76 and Hotels Under $152. Discover hotel discounts now and make your hotel reservation today.