What types of holiday rentals are available in Annapolis?

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

Are there any pet-friendly holiday rentals in Annapolis?

There are a number of dog and pet-friendly Annapolis holiday rentals, with around 14% allowing you to bring your pet along with you.

How much is a holiday rental in Annapolis for this weekend?

In the last 72 hours, users have found Annapolis holiday rentals for this weekend for as low as $274 per night.

How can I find holiday rentals near me in Annapolis?

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

Annapolis Holiday Rentals from $449/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

$603+

View availability

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis, MD, United States

8.9Very Good(4)

Parking

Free Wi-Fi

$497+

View availability

Gaia House

Annapolis, MD, United States

9.5Wonderful(32)

Parking

Free Wi-Fi

Pet-friendly

$442+

View availability

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis, MD, United States

9.9Wonderful(45)

$304+

View availability

Cozy place close to the city dock

Annapolis, MD, United States

Free Wi-Fi

$287+

View availability

Freshly renovated 3-story home 1 block from USNA!

Annapolis, MD, United States

$1,077+

View availability

Chic Condo with Balcony in the Heart of Annapolis!

Annapolis, MD, United States

9.3Wonderful(43)

Free Wi-Fi

$895+

View availability

Cozy 2br home w/ parking in downtown Annapolis

Downtown

9.1Wonderful(12)

Parking

Free Wi-Fi

$835+

View availability

Beautiful Condo - Water View Near City Dock

Annapolis, MD, United States

Free Wi-Fi

Pool

$461+

View availability

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

Annapolis, MD, United States

9.8Wonderful(54)

$843+

View availability

Waterfront home in Annapolis MD with private pier

Annapolis, MD, United States

Free Wi-Fi

$1,355+

View availability

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

Annapolis, MD, United States

Free Wi-Fi

$673+

View availability

BayRidge house by Quiet Waters, Thomas Point Parks

Annapolis, MD, United States

9.8Wonderful(7)

Parking

Free Wi-Fi

$532+

View availability

Neptune By The Water

Annapolis, MD, United States

10Wonderful(6)

Parking

Free Wi-Fi

Pet-friendly

$785+

View availability

Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA

Annapolis, MD, United States

9.6Wonderful(19)

Free Wi-Fi

$537+

View availability

Downtown Annapolis King George 3rd Floor Hideaway

Annapolis, MD, United States

Free Wi-Fi

KAYAK’s insights for holiday 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 $546. In comparison, September is the most expensive month, with prices at $1,335.

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 $537. The highest prices are found on Sunday, with average rates at $1,100.

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 holiday rental property amenities in Annapolis
Holiday rentals in Annapolis are around 53% more expensive than hotels on average. Search here to compare prices for all accommodation types in Annapolis.
The best holiday 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 travellers.
Downtown is the neighbourhood in Annapolis with the most affordable holiday rental properties (67 properties with an average price of $801 per night). Cozy 2br home w/ parking in downtown Annapolis, Perfect spot for a Weekend Getaway! and 18th Cent. Charm in Historic Downtown Annapolis are the most popular rental properties in Downtown.

See more tips

What types of holiday rentals are available in Annapolis?
There are loads of different property types that you can make your holiday home in Annapolis. You’ll find apartments, boats, condos, cottages, houses, homestays, houseboats, motorhomes and villas.
Are there any pet-friendly holiday rentals in Annapolis?
There are a number of dog and pet-friendly Annapolis holiday rentals, with around 14% allowing you to bring your pet along with you.
How much is a holiday rental in Annapolis for this weekend?
In the last 72 hours, users have found Annapolis holiday rentals for this weekend for as low as $274 per night. Search here for similar prices
How can I find holiday rentals near me in Annapolis?
Take a look at our holiday rentals map to find the best holiday rental homes near you.