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 $3,779.

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 $16,196.

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 18% allowing you to bring your pet along with you.

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 $190/night

Recommended by KAYAK

Best Annapolis vacation rentals

These are the best prices for Sep 13 - 14.

Charming Annapolis Cottage-Steps from Naval Academy & Downtown with parking.

Annapolis, MD

9.9Wonderful(44)

House

$408+

Check availability

Spectacular Location Two Bedroom State Circle Apartment

Downtown

9.4Wonderful(30)

Apartment

$521+

Check availability

Waterfront home in Annapolis MD with private pier

Annapolis, MD

House

$855+

Check availability

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Annapolis, MD

10Wonderful(50)

Apartment

$492+

Check availability

Charming Renovated Historic Home Downtown wparking

Annapolis, MD

9.7Wonderful(74)

House

$469+

Check availability

New Downtown Annapolis Condo With Free Parking

Annapolis, MD

10Wonderful(39)

Condo

$299+

Check availability

Fleet St Retreat in Downtown - Great Location!

Annapolis, MD

9.4Wonderful(44)

House

$349+

Check availability

Cozy 1st Floor King George one bedroom apartment right across from USNA

Downtown

9.7Wonderful(28)

Apartment

$252+

Check availability

Charming Historic Home .75mile to Navy Stadium, 1mile to USNA and Downtown

Annapolis, MD

9.7Wonderful(8)

House

$616+

Check availability

Studio Apartment in Downtown Annapolis

Annapolis, MD

10Wonderful(7)

Apartment

$318+

Check availability

Cozy 2br home w/ parking in downtown Annapolis

Downtown

9.6Wonderful(36)

House

$434+

Check availability

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis, MD

9.9Wonderful(133)

House

$458+

Check availability

Fisher House - Downtown Annapolis!

Downtown

9.6Wonderful(20)

House

$663+

Check availability

Annapolis Garden Suite

Annapolis, MD

10Wonderful(16)

House

$388+

Check availability

Bay View Studio Apartment

Annapolis, MD

9.9Wonderful(48)

Apartment

$386+

Check availability

Annapolis Condominium in the heart of the historic center

Downtown

9.7Wonderful(104)

Condo

$417+

Check availability

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, October is the most expensive month, with prices at $1,294.

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

Wednesday offers the lowest rates in Annapolis, with an average nightly price of $423. 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 $422 in a Apartment. House prices start at $796.

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

The best deal for a vacation rental in Annapolis found by KAYAK users for the upcoming weekend was $338 in a Apartment. Houses prices start at $584.

Find deals

Low season	High season	Average price (weeknight)	Average price (weekend night)
January	October	$582	$531
Cheapest month to stay with an average 80% drop in price.	Most expensive month to stay with an average 52% rise in price.	Average Sun - Thu price over the last 2 weeks.	Average Fri & Sat price over the last 2 weeks.

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), New Downtown Annapolis Condo With Free Parking (10.0, 39), and Recently Renovated Annapolis Home - Conveniently Located (10.0, 73), 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 $624 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 11 days.
The cheapest Annapolis vacation rental found on KAYAK in the last 2 weeks was $541, while the most expensive was $595.

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 $3,779.
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 $16,196.
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 18% 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 $422. 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 $338 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.

Annapolis vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Annapolis

Best Annapolis vacation rentals

KAYAK’s insights for vacation rentals in Annapolis

Which month has the cheapest vacation rental rates in Annapolis?

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

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

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

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

KAYAK's top tips for finding Annapolis vacation rental deals

FAQs when booking a vacation home in Annapolis

Where to stay in Annapolis?

More options for your stay in Annapolis

Complete your trip to Annapolis

Other popular hotel destinations

Stays in Annapolis