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Annapolis vacation rentals

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Best Annapolis vacation rentals

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
9.3 Wonderful
C$ 407+
C$ 407+
Parking
Free Wi-Fi
Cozy Downtown Apartment-Naval Academy Vicinity - Annapolis - Living room
Cozy Downtown Apartment-Naval Academy Vicinity
9.7 Wonderful
C$ 557+
C$ 557+
Free Wi-Fi
Cozy 2br home w/ parking in downtown Annapolis - Annapolis - Living room
Cozy 2br home w/ parking in downtown Annapolis - Annapolis - Living room
Cozy 2br home w/ parking in downtown Annapolis
9.1 Wonderful
DowntownC$ 454+
C$ 454+
Parking
Free Wi-Fi
Gaia House - Annapolis - Building
Gaia House - Annapolis - Building
Gaia House
9.6 Wonderful
C$ 248+
C$ 248+
Parking
Free Wi-Fi
Pet friendly
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District - Annapolis - Building
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District - Annapolis - Building
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
9.9 Wonderful
C$ 300+
C$ 300+
Brand new Renovation in Historic District with 2 parking spots -walk everywhere - Annapolis - Living room
Brand new Renovation in Historic District with 2 parking spots -walk everywhere - Annapolis - Living room
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
C$ 380+
C$ 380+
Free Wi-Fi
Pet friendly
Cozy place close to the city dock - Annapolis - Bedroom
Cozy place close to the city dock - Annapolis - Bedroom
Cozy place close to the city dock
C$ 265+
C$ 265+
Free Wi-Fi
Chic Condo with Balcony in the Heart of Annapolis! - Annapolis - Living room
Chic Condo with Balcony in the Heart of Annapolis! - Annapolis - Living room
Chic Condo with Balcony in the Heart of Annapolis!
9.6 Wonderful
C$ 564+
C$ 564+
Free Wi-Fi
Annapolis waterfront \'tiny house\' in garden setting - Annapolis - Living room
Annapolis waterfront \'tiny house\' in garden setting - Annapolis - Living room
Annapolis waterfront \'tiny house\' in garden setting
C$ 278+
C$ 278+
Freshly renovated 3-story home 1 block from USNA! - Annapolis - Bedroom
Freshly renovated 3-story home 1 block from USNA! - Annapolis - Bedroom
Freshly renovated 3-story home 1 block from USNA!
C$ 933+
C$ 933+
BayRidge house by Quiet Waters, Thomas Point Parks - Annapolis - Bedroom
BayRidge house by Quiet Waters, Thomas Point Parks - Annapolis - Bedroom
BayRidge house by Quiet Waters, Thomas Point Parks
9.8 Wonderful
C$ 458+
C$ 458+
Parking
Free Wi-Fi
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun! - Annapolis - Living room
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun! - Annapolis - Living room
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
9.8 Wonderful
C$ 784+
C$ 784+
Neptune By The Water - Annapolis - Bedroom
Neptune By The Water - Annapolis - Bedroom
Neptune By The Water
10 Wonderful
C$ 724+
C$ 724+
Parking
Free Wi-Fi
Pet friendly
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis - Annapolis - Building
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis - Annapolis - Building
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
C$ 389+
C$ 389+
Free Wi-Fi
Pristine Downtown 1-Bedroom Steps from State House - Annapolis - Living room
Pristine Downtown 1-Bedroom Steps from State House - Annapolis - Living room
Pristine Downtown 1-Bedroom Steps from State House
DowntownC$ 488+
C$ 488+
Free Wi-Fi
Beautiful Condo - Water View Near City Dock - Annapolis - Pool
Beautiful Condo - Water View Near City Dock - Annapolis - Pool
Beautiful Condo - Water View Near City Dock
C$ 386+
C$ 386+
Free Wi-Fi
Pool
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C$ 151 - C$ 495C$ 495 - C$ 839C$ 839 - C$ 1,183C$ 1,183 - C$ 1,526C$ 1,526+ per night

Property Types

ApartmentCondoCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

July

High season

October
Cheapest month to stay with an average 46% drop in price.
Most expensive month to stay with an average 23% rise in price.

When to book a vacation rental in Annapolis

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

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 Beautiful Condo - Water View Near City Dock (10.0, 27 reviews), Cozy Cottage by the Beach - WaterviewbrMinutes from Downtown Annapolis (10.0, 40), and Pristine Downtown 1-Bedroom Steps from State House (10.0, 20), based on ratings and reviews from real travelers.
  • Book your Annapolis vacation rental more than 90 days before your stay begins to get the best price.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Annapolis for 3 days.
See more tips

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 C$ 4,192.

  • 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 C$ 17,965.

  • 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 and houses.

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

    There are a number of dog and pet-friendly Annapolis vacation rentals, with around 17% 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 C$ 482. 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 C$ 479 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.

  • How much is a vacation rental in Annapolis?

    KAYAK users have found vacation rentals in Annapolis for as cheap as C$ 469 in the last 3 days. The average price is C$ 599.

See more FAQs

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

Annapolis vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Annapolis. Find cheap vacation homes to rent in Annapolis. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Annapolis that suits you best.

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