Vacation rentals in Annapolis

Search and compare Annapolis, MD vacation 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.

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

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

Travel insights for vacation rentals in Annapolis

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 507). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is C$ 1,028.
Find deals

Other accommodations in Annapolis

Find the perfect vacation 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 .
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
C$ 104
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
C$ 130
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
C$ 323
Avg. per night
View Deal
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
C$ 170
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
C$ 336
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
C$ 151
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.
Use the map to find vacation rentals in Annapolis that are close to the points of interest you'll be frequenting. 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 9 September 2025.

  • How much does a vacation rental in Annapolis cost?

    Annapolis vacation rentals are C$ 545/night on average. However, you may find that prices fluctuate depending on the time of year. For example, October is the most expensive month to book a vacation rental in Annapolis, and March is often the cheapest month to book. Recently, our users found rentals for C$ 58/night - which is currently the cheapest price. Keep in mind that anything C$ 512/night or less is still considered a good deal.

  • What part of Annapolis is best to stay in?

    Downtown is the best part of Annapolis to stay in based on our user data. Out of all our users who looked at Annapolis vacation rentals, 94% of them looked for stays in the Downtown neighbourhood in the last year. The Cozy 2br home w/ parking in downtown Annapolis happens to be the most popular vacation rental in the Downtown neighbourhood of Annapolis.

  • Are there any Inn vacation rentals in Annapolis?

    Yes, there are 2 Inn vacation rentals in Annapolis. According to our data, Village Inn is currently the most popular Inn rental in the city.

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.
Annapolis Bed & Breakfasts
Annapolis Inns
Annapolis Motels
Annapolis Resorts

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 hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly. Discover hotel discounts now and make your hotel reservation today.