Annapolis vacation rentals

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Best Annapolis vacation rentals

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$160 - $375$375 - $590$590 - $805$805 - $1,019$1,019+ per night

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Most recommended vacation rentals in Annapolis

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Bay Ridge unit by Downtown Annapolis and Quiet Waters Park - Annapolis - Living room
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis, MD
9.0Wonderful(8)
Parking
Free Wi-Fi
$346+
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Cozy Downtown Apartment-Naval Academy Vicinity - Annapolis - Living room
Cozy Downtown Apartment-Naval Academy Vicinity
Annapolis, MD
9.6Wonderful(47)
Free Wi-Fi
$385+
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Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District - Annapolis - Building
Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District
Annapolis, MD
9.9Wonderful(61)
$194+
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Waterfront home in Annapolis MD with private pier - Annapolis - Living room
Waterfront home in Annapolis MD with private pier
Annapolis, MD
Free Wi-Fi
$887+
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BayRidge house by Quiet Waters, Thomas Point Parks - Annapolis - Bedroom
BayRidge house by Quiet Waters, Thomas Point Parks
Annapolis, MD
9.7Wonderful(10)
Parking
Free Wi-Fi
$323+
Check availability
Beautiful Condo - Water View Near City Dock - Annapolis - Outdoors view
Beautiful Condo - Water View Near City Dock
Annapolis, MD
9.9Wonderful(41)
Free Wi-Fi
Pool
$282+
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Neptune By The Water - Annapolis - Bedroom
Neptune By The Water
Annapolis, MD
9.8Wonderful(10)
Parking
Free Wi-Fi
Pet friendly
$551+
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA - Annapolis - Patio
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Annapolis, MD
9.6Wonderful(25)
Free Wi-Fi
$325+
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Cozy 2br home w/ parking in downtown Annapolis - Annapolis - Living room
Cozy 2br home w/ parking in downtown Annapolis
Downtown
9.5Wonderful(23)
Parking
Free Wi-Fi
$383+
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18th Cent. Charm in Historic Downtown Annapolis - Annapolis - Bedroom
18th Cent. Charm in Historic Downtown Annapolis
Annapolis, MD
9.2Wonderful(5)
$395+
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Fisher House - Downtown Annapolis! - Annapolis - Kitchen
Fisher House - Downtown Annapolis!
Downtown
9.9Wonderful(13)
Free Wi-Fi
Pet friendly
$653+
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Spacious 2nd Floor Apartment, with its own entrance and off-street parking. - Annapolis - Living room
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Annapolis, MD
10Wonderful(6)
Free Wi-Fi
$368+
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Freshly renovated 3-story home 1 block from USNA! - Annapolis - Bedroom
Freshly renovated 3-story home 1 block from USNA!
Annapolis, MD
9.8Wonderful(32)
$674+
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Stylish + fresh bungalow 2 blocks from N-MC Stadium - Annapolis - Building
Stylish + fresh bungalow 2 blocks from N-MC Stadium
Annapolis, MD
9.0Wonderful(10)
Parking
Free Wi-Fi
Pet friendly
$534+
Check availability
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis - Annapolis - Bedroom
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Annapolis, MD
9.4Wonderful(29)
Free Wi-Fi
$307+
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Downtown Annapolis King George 3rd Floor Hideaway - Annapolis
Downtown Annapolis King George 3rd Floor Hideaway
Annapolis, MD
9.6Wonderful(14)
Free Wi-Fi
$312+
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Booking Insights

KAYAK’s insights for vacation rentals in Annapolis

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Annapolis with confidence.

What is the cheapest day of the week to book a vacation rental in Annapolis?

Thursday offers the lowest rates in Annapolis, with an average nightly price of $264. The highest prices are found on Saturday, with average rates at $538.

How early should you book a vacation rental in Annapolis?

Book at least 76 days before your stay begins to get the best price for your Annapolis vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

March
July
$335
$488
Cheapest month to stay with an average 69% drop in price.
Most expensive month to stay with an average 44% 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 56% 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 Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! (9.9, 45 reviews), Beautiful Condo - Water View Near City Dock (9.9, 41), and Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District (9.9, 61), based on ratings and reviews from real travelers.
  • 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 March and June.
  • The cheapest night for renting a vacation home in Annapolis is Thursday. 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 8 days.

FAQs when booking a vacation home in Annapolis

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

    The average price for a weekly Annapolis vacation rental found by KAYAK users in the last 2 weeks is $3,649.

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

    The average price for a monthly Annapolis vacation rental found by KAYAK users in the last 2 weeks is $15,640.

  • 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, boats, condos, cottages, houses, homestays, hotels, houseboats, recreational vehicles 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 11% 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 $368. 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

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