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 $3,552.

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 $15,222.

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, houseboats and villas.

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 $500.

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 $370 per night.

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 $268/night

Recommended by KAYAK

Best Annapolis vacation rentals

These are the best prices for May 13 - 14.

Charming Cottage 2 parking spot easy walk downtown

Annapolis, MD

9.9Wonderful(43)

House

$434+

Check availability

Spectacular Location Two Bedroom State Circle Apartment

Downtown

Apartment

Annapolis, MD

House

$494+

Check availability

Walk to the stadium, downtown, West St - close to everything

Annapolis, MD

9.6Wonderful(10)

House

$342+

Check availability

Charming Renovated Historic Home Downtown wparking

Annapolis, MD

9.6Wonderful(70)

House

$431+

Check availability

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

Annapolis, MD

10Wonderful(46)

Apartment

$529+

Check availability

Charming Historic Townhouse Steps From Usna

Downtown

10Wonderful(31)

House

$380+

Check availability

Fisher House - Downtown Annapolis!

Downtown

9.7Wonderful(18)

House

$518+

Check availability

Waterfront Oasis Of Annapolis Star

Annapolis, MD

9.9Wonderful(42)

Apartment

$490+

Check availability

Studio Apartment in Downtown Annapolis

Annapolis, MD

10Wonderful(5)

Apartment

$326+

Check availability

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

Annapolis, MD

9.7Wonderful(8)

House

$601+

Check availability

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

Downtown

9.7Wonderful(28)

Apartment

$318+

Check availability

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

Annapolis, MD

9.9Wonderful(131)

House

$497+

Check availability

Across From Stadium - Walk To Downtown Annapolis.

Annapolis, MD

9.3Wonderful(36)

House

$433+

Check availability

Coastal Edgewater Home with Private Hot Tub!

Annapolis, MD

8.8Very good(10)

House

$445+

Check availability

Cozy Downtown Apartment-Naval Academy Vicinity

Annapolis, MD

9.5Wonderful(48)

Apartment

$349+

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.

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

Tuesday offers the lowest rates in Annapolis, with an average nightly price of $190. The highest prices are found on Friday, with average rates at $719.

Find deals

Low season	High season	Average price (weeknight)	Average price (weekend night)
February	April	$396	$709
Cheapest month to stay with an average 66% drop in price.	Most expensive month to stay with an average 41% 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 15% 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, 46 reviews), Charming Historic Townhouse Steps From Usna (10.0, 31), and Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis (10.0, 26), based on ratings and reviews from real travelers.
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 February and January.
The cheapest night for renting a vacation home in Annapolis is Tuesday. In contrast, the most expensive is Friday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Annapolis for 15 days.

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 $3,552.
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 $15,222.
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, houseboats and villas.
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 $500. 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 $370 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.

Everything you need to know for your stay in Annapolis

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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

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Annapolis with confidence.

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

Tuesday offers the lowest rates in Annapolis, with an average nightly price of $190. The highest prices are found on Friday, with average rates at $719.

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

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 $3,552.

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 $15,222.

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, houseboats and villas.

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 $500. 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 $370 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?

Everything you need to know for your stay in Annapolis

Hotels near airports in Annapolis

Complete your trip to Annapolis

Popular hotel types in Annapolis

Hotels in popular neighborhoods in Annapolis

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Stays in Annapolis