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Holiday rentals in Annapolis, MD

Find deals on 511 holiday rentals in Annapolis, MD

Annapolis, MD, United States
1 Mar — 2 Mar2

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Top rentals in Annapolis

Find the perfect holiday rental for your stay in Annapolis
Price
£110
£456
Review Score
0+
6+
7+
8+
9+

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

Cozy place close to the city dock Photo

Cozy place close to the city dock

Annapolis, MD, United States

10.0

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

Annapolis, MD, United States

Cheerful 3-Bedroom House in Downtown Annapolis Photo

Cheerful 3-Bedroom House in Downtown Annapolis

Annapolis, MD, United States

10.0

Available for Maryland Legislative Session 2024 ! Perfect location!

Annapolis, MD, United States

8.8
New Loft w/South River view from treehouse deck! Photo

New Loft w/South River view from treehouse deck!

Riva, MD, United States

10.0

Get the best value holiday rental in Annapolis

These Annapolis holiday rentals have the best prices for their ratings
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District Photo

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis, MD, United States

9.9
Usna Getaway Photo

Usna Getaway

Annapolis, MD, United States

9.9
Annapolis Escape Steps to Harbor backs to Gate 1 Photo

Annapolis Escape Steps to Harbor backs to Gate 1

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
Entire Private 2 bedrooms house, nice neighborhood Photo

Entire Private 2 bedrooms house, nice neighborhood

Arnold, MD, United States

9.3
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park Photo

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis, MD, United States

8.9

momondo's favourite holiday rentals in Annapolis

Learn more about these user-preferred holiday rentals in Annapolis
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
£187
Waterfront Getaway, Dock Your Boat & Play! Photo

Waterfront Getaway, Dock Your Boat & Play!

Edgewater, MD, United States

£164
Captain's Quarters - Eastport! Photo

Captain's Quarters - Eastport!

Annapolis, MD, United States

8.6
£310
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !! Photo

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

Annapolis, MD, United States

9.8
£209
Pristine Downtown 1-Bedroom Steps from State House Photo

Pristine Downtown 1-Bedroom Steps from State House

Annapolis, MD, United States

10.0
£338
Waterfront home in Annapolis MD with private pier Photo

Waterfront home in Annapolis MD with private pier

Annapolis, MD, United States

£683
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
£294
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
£261
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
£319
Waterfront Annapolis Home Fire Pit and Fishing Pier Photo

Waterfront Annapolis Home Fire Pit and Fishing Pier

Annapolis, MD, United States

9.4
£262
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
£479
Weems Creek Cottage, Annapolis Waterfront Photo

Weems Creek Cottage, Annapolis Waterfront

Annapolis, MD, United States

9.9
£198
Charming 3 BR/2BA home at Arundel on the Bay features a community beach, boat slips, playground. Photo

Charming 3 BR/2BA home at Arundel on the Bay features a community beach, boat slips, playground.

Annapolis, MD, United States

10.0
£524
Historic Annapolis Home 1.5 blocks from center of town. Photo

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis, MD, United States

9.7
£285
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
£224
Usna Quintessential Charm ~ Downtown Annapolis. Photo

Usna Quintessential Charm ~ Downtown Annapolis.

Annapolis, MD, United States

8.5
£208
Usna Getaway Photo

Usna Getaway

Annapolis, MD, United States

9.9
£174
Vintage Charm: Annapolis Retreat Photo

Vintage Charm: Annapolis Retreat

Annapolis, MD, United States

10.0
£293
Annapolis/Eastport Private Beautiful Apt- 1 Mile Walk To Downtown Photo

Annapolis/Eastport Private Beautiful Apt- 1 Mile Walk To Downtown

Annapolis, MD, United States

9.9
£175
Heart of Historic District! Photo

Heart of Historic District!

Annapolis, MD, United States

9.8
£461

Useful insights on Annapolis holiday rentals

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

Lowest Holiday Rental Price

£111
The cheapest price for a room in Annapolis found in the last 7 days is £111/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 seasonMarchmost expensive time to stay
48%expected price decrease
37%expected price increase

Price

£157 - £472

Cheapest day of weekMondayis the cheapest day of the week to book
Highest day of weekThursdayis the most expensive day of the week to book
£286
£508

Information about staying in Annapolis

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

How long do people typically book holiday apartments for in Annapolis?

About 3 nights is the most common choice for those booking holiday apartment rentals 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 48% cheaper in February vs. the high season.

How many operators does momondo search for hotels in Annapolis?

There are 551 operators available for hotels in Annapolis as of February 2025.

When did momondo last update prices for hotels in Annapolis?

Prices for hotels in Annapolis are updated daily.

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