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Holiday rentals in Annapolis, MD

Find deals on 511 holiday rentals in Annapolis, MD

Annapolis, MD, United States
7 May — 8 May2

momondo compares 3M+ hotel and accommodation options.

Top rentals in Annapolis

Find the perfect holiday rental for your stay in Annapolis
Price
$245
$1,356
Review Score
0+
6+
7+
8+
9+

Vacation rentals in popular neighbourhoods in Annapolis

Below are the most popular neighbourhoods in Annapolis to stay in, as well as some of the best vacation rentals in each area
Downtown
Search rentals in Downtown
The Little House Photo
Best value

The Little House

Annapolis, MD, United States

7.9
18th Cent. Charm in Historic Downtown Annapolis Photo
No. 1 most popular

18th Cent. Charm in Historic Downtown Annapolis

Annapolis, MD, United States

Perfect spot for a Weekend Getaway! Photo
No. 2 most popular

Perfect spot for a Weekend Getaway!

Annapolis, MD, United States

10.0
Fisher House - Downtown Annapolis! Photo
No. 3 most popular

Fisher House - Downtown Annapolis!

Annapolis, MD, United States

9.9
Pristine Downtown 1-Bedroom Steps from State House Photo
No. 4 most popular

Pristine Downtown 1-Bedroom Steps from State House

Annapolis, MD, United States

10.0

Hostels and cheap hotels in Annapolis

These hotels and hostels usually make for a cheap way to stay in Annapolis
Private Cozy Basement Apartment Photo

Private Cozy Basement Apartment

Arnold, MD, United States

Gaia House Photo

Gaia House

Annapolis, MD, United States

9.5

Bright and cheery home. Just a short 2 blocks from the beach.

Annapolis, MD, United States

Anchors Away Abode Photo

Anchors Away Abode

Annapolis, MD, United States

9.8
Cozy place close to the city dock Photo

Cozy place close to the city dock

Annapolis, MD, United States

10.0
Usna Getaway Photo

Usna Getaway

Annapolis, MD, United States

9.9

Get the best value holiday rental in Annapolis

These Annapolis holiday rentals have the best prices for their ratings
Gaia House Photo

Gaia House

Annapolis, MD, United States

9.5
BayRidge house by Quiet Waters, Thomas Point Parks Photo

BayRidge house by Quiet Waters, Thomas Point Parks

Annapolis, MD, United States

9.8
Usna Getaway Photo

Usna Getaway

Annapolis, MD, United States

9.9
Neptune By The Water Photo

Neptune By The Water

Annapolis, MD, United States

10.0
Anchors Away Abode Photo

Anchors Away Abode

Annapolis, MD, United States

9.8
Entire Private 2 bedrooms house, nice neighborhood Photo

Entire Private 2 bedrooms house, nice neighborhood

Arnold, MD, United States

9.3

momondo's favourite holiday rentals in Annapolis

Learn more about these user-preferred holiday rentals in Annapolis
Waterfront Getaway, Dock Your Boat & Play! Photo

Waterfront Getaway, Dock Your Boat & Play!

Edgewater, MD, United States

$359
Captain's Quarters - Eastport! Photo

Captain's Quarters - Eastport!

Annapolis, MD, United States

8.6
$503
Fisher House - Downtown Annapolis! Photo

Fisher House - Downtown Annapolis!

Annapolis, MD, United States

9.9
$648
Pristine Downtown 1-Bedroom Steps from State House Photo

Pristine Downtown 1-Bedroom Steps from State House

Annapolis, MD, United States

10.0
$447
Usna Home Downtown Annapolis Photo

Usna Home Downtown Annapolis

Annapolis, MD, United States

8.5
$462
Steps to Naval Academy, City Dock, and State House Photo

Steps to Naval Academy, City Dock, and State House

Annapolis, MD, United States

9.9
$626
Beautiful Waterfront Townhome In Historic Annapolis Photo

Beautiful Waterfront Townhome In Historic Annapolis

Annapolis, MD, United States

9.4
$1,246

Brand new Renovation in Historic District with 2 parking spots -walk everywhere

Annapolis, MD, United States

9.9
$448
Charming garden row home, easy 4 block walk to the heart of Annapolis. Photo

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis, MD, United States

10.0
$668
Cozy Cottage by the Beach - WaterviewbrMinutes from Downtown Annapolis Photo

Cozy Cottage by the Beach - WaterviewbrMinutes from Downtown Annapolis

Annapolis, MD, United States

10.0
$650
Eastport Cottage .5 mi from Downtown Annapolis\n\n Photo

Eastport Cottage .5 mi from Downtown Annapolis\n\n

Annapolis, MD, United States

10.0
$614
Waterfront Annapolis Home Fire Pit and Fishing Pier Photo

Waterfront Annapolis Home Fire Pit and Fishing Pier

Annapolis, MD, United States

9.4
$598
Modern Comfort meets Mid Century Charm at One-level home, with 4 King Beds and dog-friendly Photo

Modern Comfort meets Mid Century Charm at One-level home, with 4 King Beds and dog-friendly

Annapolis, MD, United States

9.6
$821
Anchor's Away In The Heart Of Eastport! Photo

Anchor's Away In The Heart Of Eastport!

Annapolis, MD, United States

9.9
$603
Bay View Studio Apartment Photo

Bay View Studio Apartment

Annapolis, MD, United States

10.0
$557
Coastal Cottage - 3 Br -Retreat Near Annapolis | Bay Views | Beach Access Photo

Coastal Cottage - 3 Br -Retreat Near Annapolis | Bay Views | Beach Access

Annapolis, MD, United States

10.0
$1,379
Spacious 2nd Floor Apartment, with its own entrance and off-street parking. Photo

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

Annapolis, MD, United States

10.0
$532
Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier! Photo

Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!

Annapolis, MD, United States

9.7
$634
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport Photo

Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport

Annapolis, MD, United States

10.0
$490
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break\n Photo

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break\n

Annapolis, MD, United States

9.9
$551

Useful insights on Annapolis holiday rentals

Get a quick overview on price and accommodation trends for your visit in Annapolis

Lowest Holiday Rental Price

$245
The cheapest price for a room in Annapolis found in the last 7 days is $245/night. This rate is available with Cozy place close to the city dock.

When to book a holiday rental in Annapolis

Check out the information below to find the best deal on a holiday rental in Annapolis
Low seasonFebruarycheapest month to stay
High seasonSeptembermost expensive time to stay
38%expected price decrease
35%expected price increase

Price

$349 - $855

Cheapest day of weekMondayis the cheapest day of the week to book
Highest day of weekSundayis the most expensive day of the week to book
$344
$705

Information about staying in Annapolis

Read these important travel tips before booking a vacation rental in Annapolis

When is the best time to book a holiday rental in Annapolis?

The cheapest month to rent a holiday apartment in Annapolis is usually February. The cost of your apartment or rental property can be around 38% cheaper in February vs. the high season.

How many operators does momondo search for hotels in Annapolis?

As of April 2025, there are 553 operators available to choose from for hotels in Annapolis.

When did momondo last update prices for hotels in Annapolis?

Prices for hotels in Annapolis are updated daily.

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