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 $2,613.

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 $11,197.

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 $253.

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 $173/night

Recommended by KAYAK

Best Annapolis vacation rentals

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Annapolis, MD

9.1Wonderful(5)

Parking

Free Wi-Fi

$304+

Check availability

Cozy Downtown Apartment-Naval Academy Vicinity

Annapolis, MD

9.7Wonderful(38)

Free Wi-Fi

$386+

Check availability

Cozy Home in Beautiful Annapolis

Annapolis, MD

9.5Wonderful(32)

Free Wi-Fi

$283+

Check availability

Beautiful Condo - Water View Near City Dock

Annapolis, MD

Free Wi-Fi

Pool

$295+

Check availability

Cozy place close to the city dock

Annapolis, MD

Free Wi-Fi

$173+

Check availability

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis, MD

9.9Wonderful(45)

$198+

Check availability

Cozy 2br home w/ parking in downtown Annapolis

Downtown

9.1Wonderful(12)

Parking

Free Wi-Fi

$569+

Check availability

Waterfront home in Annapolis MD with private pier

Annapolis, MD

Free Wi-Fi

$817+

Check availability

Water-view condo with rooftop pool & balcony - minutes from downtown

Annapolis, MD

$192+

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Chic Condo w/ Balcony in the Heart of Annapolis!

Annapolis, MD

9.4Wonderful(43)

Free Wi-Fi

$440+

Check availability

BayRidge house by Quiet Waters, Thomas Point Parks

Annapolis, MD

9.7Wonderful(8)

Parking

Free Wi-Fi

Annapolis, MD

Parking

Free Wi-Fi

Pet friendly

$595+

Check availability

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

Annapolis, MD

9.8Wonderful(54)

$454+

Check availability

Waterfront Oasis Of Annapolis Star

Annapolis, MD

Free Wi-Fi

Pool

$483+

Check availability

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

Annapolis, MD

Free Wi-Fi

$340+

Check availability

Freshly renovated 3-story home 1 block from USNA!

Annapolis, MD

$772+

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Useful Info

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 November, with average rates of $137. In comparison, July is the most expensive month, with prices at $797.

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 $264. The highest prices are found on Friday, with average rates at $809.

How early should you book a vacation rental in Annapolis?

Book at least 65 days before your stay begins to get the best price for your Annapolis vacation rental.

Find deals

Low season	November
High season	July
Average price (weeknight)	$339
Average price (weekend night)	$679

Cheapest month to stay with an average 63% drop in price.

Most expensive month to stay with an average 114% 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 63% 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 Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District (9.9, 45 reviews), Weems Creek Cottage, Annapolis Waterfront (9.9, 58), and A Quiet Retreat just steps from Naval Academy and all the Downtown Fun! (9.8, 54), based on ratings and reviews from real travelers.
Downtown is the neighborhood in Annapolis with the most affordable vacation rental properties (69 properties with an average price of $656 per night). Cozy 2br home w/ parking in downtown Annapolis, Fisher House - Downtown Annapolis!, and 18th Cent. Charm in Historic 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 November and February.
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 9 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 $2,613.
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 $11,197.
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 $253. 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 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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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 November, with average rates of $137. In comparison, July is the most expensive month, with prices at $797.

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 $264. The highest prices are found on Friday, with average rates at $809.

How early should you book a vacation rental in Annapolis?

Book at least 65 days before your stay begins to get the best price for your Annapolis vacation rental.

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?

How much is a vacation rental for a month in Annapolis?

What types of vacation rentals are available in Annapolis?

Are there any pet-friendly vacation rentals in Annapolis?

How much is a vacation rental in Annapolis for tonight?

How can I find vacation rentals near me in Annapolis?

Where to stay in Annapolis?

Everything you need to know for your stay in Annapolis

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