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Annapolis vacation rentals

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Booking Insights
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Best Annapolis vacation rentals

These are the best prices for Oct 17 - 18.
Charming Annapolis Cottage-Steps from Naval Academy & Downtown with parking. - Annapolis - Living room
Charming Annapolis Cottage-Steps from Naval Academy & Downtown with parking.
Annapolis, MD
9.9Wonderful(45)
House
$416+
Check availability
Spectacular Location Two Bedroom State Circle Apartment - Annapolis - Kitchen
Spectacular Location Two Bedroom State Circle Apartment
Downtown
9.4Wonderful(31)
Apartment
$530+
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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
House
$855+
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Studio Apartment in Downtown Annapolis - Annapolis - Bedroom
Studio Apartment in Downtown Annapolis
Annapolis, MD
9.8Wonderful(12)
Apartment
$278+
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Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids - Annapolis - Bedroom
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Annapolis, MD
10Wonderful(50)
Apartment
$538+
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Charming Renovated Historic Home Downtown wparking - Annapolis - Dining room
Charming Renovated Historic Home Downtown wparking
Annapolis, MD
9.7Wonderful(75)
House
$478+
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Fleet St Retreat in Downtown - Great Location! - Annapolis - Living room
Fleet St Retreat in Downtown - Great Location!
Annapolis, MD
9.4Wonderful(46)
House
$330+
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Fisher House - Downtown Annapolis! - Annapolis - Patio
Fisher House - Downtown Annapolis!
Downtown
9.7Wonderful(22)
House
$729+
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Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! - Annapolis - Living room
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis, MD
9.9Wonderful(142)
House
$462+
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Cozy 1st Floor King George one bedroom apartment right across from USNA - Annapolis - Living room
Cozy 1st Floor King George one bedroom apartment right across from USNA
Downtown
9.5Wonderful(29)
Apartment
$274+
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Bay View Studio Apartment - Annapolis - Living room
Bay View Studio Apartment
Annapolis, MD
9.9Wonderful(50)
Apartment
$387+
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking! - Annapolis - Balcony
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Annapolis, MD
9.8Wonderful(109)
House
$702+
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District - Annapolis - Dining room
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Annapolis, MD
9.8Wonderful(82)
Apartment
$194+
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Cozy 2br home w/ parking in downtown Annapolis - Annapolis - Living room
Cozy 2br home w/ parking in downtown Annapolis
Downtown
9.6Wonderful(39)
House
$486+
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Tranquility Awaits - Annapolis - Front desk
Tranquility Awaits
Annapolis, MD
10Wonderful(25)
Apartment
$232+
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Vintage Charm: Annapolis Retreat - Annapolis
Vintage Charm: Annapolis Retreat
Annapolis, MD
9.7Wonderful(10)
House
$346+
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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.

Which month has the cheapest vacation rental rates in Annapolis?

Vacation rentals are cheapest in Annapolis in December, with average rates of $42. In comparison, August is the most expensive month, with prices at $2,012.

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

Saturday offers the lowest rates in Annapolis, with an average nightly price of $380. The highest prices are found on Tuesday, with average rates at $1,008.

How much is a vacation rental in Annapolis for tonight by property type?

The best deal for a vacation rental in Annapolis found by KAYAK users in the last 5 days was $456 in a Condo. House prices start at $604.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
June
$557
$546
Cheapest month to stay with an average 79% drop in price.
Most expensive month to stay with an average 40% 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 22% 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 Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids (10.0, 50 reviews), Tranquility Awaits (10.0, 25), and Relaxing Oasis 5 Min To Navy Stadium, St Johns, Naval Academy & Downtown (10.0, 64), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Annapolis with the most affordable vacation rental properties (39 properties with an average price of $634 per night). Spectacular Location Two Bedroom State Circle Apartment, Cozy 1st Floor King George one bedroom apartment right across from USNA, and Cozy 2br home w/ parking in downtown Annapolis 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 January and March.
  • The cheapest night for renting a vacation home in Annapolis is Wednesday. In contrast, the most expensive is Tuesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Annapolis for 9 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 $3,616.

  • 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 $15,496.

  • 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 and houseboats.

  • 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 19% 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 $456. 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 $874 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.

More options for your stay in Annapolis