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, houseboats, recreational vehicles and villas.

Are there any pet-friendly vacation rentals in Annapolis?

There are a number of dog and pet-friendly Annapolis vacation rentals, with around 14% 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$ 571.

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.

Annapolis Vacation Rentals from C$ 353/night

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Best Annapolis vacation rentals

Cozy Downtown Apartment-Naval Academy Vicinity

Annapolis, MD, United States

9.7Wonderful(37)

Free Wi-Fi

C$ 534+

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Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis, MD, United States

8.9Very good(4)

Parking

Free Wi-Fi

C$ 440+

Check availability

Gaia House

Annapolis, MD, United States

9.5Wonderful(32)

Parking

Free Wi-Fi

Pet friendly

C$ 392+

Check availability

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis, MD, United States

9.9Wonderful(45)

C$ 270+

Check availability

Cozy place close to the city dock

Annapolis, MD, United States

Free Wi-Fi

C$ 255+

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Freshly renovated 3-story home 1 block from USNA!

Annapolis, MD, United States

C$ 955+

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Chic Condo with Balcony in the Heart of Annapolis!

Annapolis, MD, United States

9.3Wonderful(43)

Free Wi-Fi

C$ 793+

Check availability

Cozy 2br home w/ parking in downtown Annapolis

Downtown

9.1Wonderful(12)

Parking

Free Wi-Fi

C$ 741+

Check availability

Beautiful Condo - Water View Near City Dock

Annapolis, MD, United States

Free Wi-Fi

Pool

C$ 408+

Check availability

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Annapolis, MD, United States

9.8Wonderful(54)

C$ 747+

Check availability

Waterfront home in Annapolis MD with private pier

Annapolis, MD, United States

Free Wi-Fi

C$ 1,201+

Check availability

Spacious 2nd Floor Apartment, with its own entrance and off-street parking.

Annapolis, MD, United States

Free Wi-Fi

C$ 597+

Check availability

BayRidge house by Quiet Waters, Thomas Point Parks

Annapolis, MD, United States

9.8Wonderful(7)

Parking

Free Wi-Fi

C$ 472+

Check availability

Neptune By The Water

Annapolis, MD, United States

10Wonderful(6)

Parking

Free Wi-Fi

Pet friendly

C$ 696+

Check availability

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Annapolis, MD, United States

9.6Wonderful(19)

Free Wi-Fi

C$ 476+

Check availability

Downtown Annapolis King George 3rd Floor Hideaway

Annapolis, MD, United States

Free Wi-Fi

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 February, with average rates of C$ 429. In comparison, September is the most expensive month, with prices at C$ 1,049.

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

Monday offers the lowest rates in Annapolis, with an average nightly price of C$ 422. The highest prices are found on Sunday, with average rates at C$ 865.

How early should you book a vacation rental in Annapolis?

Book at least 66 days before your stay begins to get the best price for your Annapolis vacation rental.

Find 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.
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

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, houseboats, recreational vehicles and villas.
Are there any pet-friendly vacation rentals in Annapolis?
There are a number of dog and pet-friendly Annapolis vacation rentals, with around 14% 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$ 571. 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.