Annapolis vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Annapolis

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Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
May
$389
$329
Cheapest month to stay with an average 88% drop in price.
Most expensive month to stay with an average 454% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Annapolis vacation rental deals

  • Pool and pet friendly are the most popular vacation rental property amenities in Annapolis
  • Vacation rentals in Annapolis are around 60% more expensive than hotels on average. Search here to compare prices for all accommodation types in Annapolis.
  • The best vacation rental properties in Annapolis are Charming Historic Townhouse Steps From Usna (10.0, 31 reviews), Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids (10.0, 45), and Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! (10.0, 128), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Annapolis with the most affordable vacation rental properties (41 properties with an average price of $627 per night). Cozy 2br home w/ parking in downtown Annapolis, Fisher House - Downtown Annapolis!, and Midcentury Modern Getaway Prime Location are the most popular rental properties in Downtown.
  • If you’re looking for a cheap vacation rental in Annapolis, you should consider visiting during the low season. The cheapest vacation homes in Annapolis can be found in April and February.
  • The cheapest night for renting a vacation home in Annapolis is Friday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Annapolis for 14 days.

FAQs when booking a vacation home in Annapolis

  • What types of vacation rentals are available in Annapolis?

    There are loads of different property types that you can make your vacation home in Annapolis. You’ll find apartments, condos, cottages, houses, homestays, hotels, houseboats and villas.

  • What are some of the most-loved vacation rentals available in Annapolis?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Candlewood Suites Annapolis By IHG.

  • Are there any pet-friendly vacation rentals in Annapolis?

    There are a number of dog and pet-friendly Annapolis vacation rentals, with around 5% allowing you to bring your pet along with you.

  • How much is a vacation rental in Annapolis for tonight?

    In the last 72 hours, users have found Annapolis vacation rentals for tonight for as low as $634. Search here for similar prices

  • How much is a vacation rental in Annapolis for this weekend?

    In the last 72 hours, users have found Annapolis vacation rentals for this weekend for as low as $325 per night. Search here for similar prices

  • How can I find vacation rentals near me in Annapolis?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Annapolis?

Our map will help you find the perfect place to stay in Annapolis by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Annapolis