Annapolis Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Annapolis vacation rentals

A dining area with a wooden table, cushioned chairs, and a bench. There is a window with curtains, a wall clock, and a framed picture.

1. Walk to Dtwn Rockville! Prairie-inspired Retreat

Walk to Dtwn Rockville! Prairie-inspired Retreat
3.0 star property
Rockville
The price is P9,457
P24,180 total
includes taxes & fees
Nov 10 - Nov 11
Walk to Dtwn Rockville! Prairie-inspired Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
Condo image
Condos
Condos

Find out more about Annapolis

Search for holiday rentals in Annapolis on Expedia! You can easily find your home rentals, villas, holiday apartments in Annapolis using one of the methods below:

  • View our selection of featured holiday rentals in Annapolis
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annapolis while they last

Look no further and take a look at our great range of rental properties in Annapolis!

Frequently Asked Questions

Can I find vacation rentals in Annapolis?

Yes, we give you a choice of vacation rentals close to popular attractions in Annapolis, or you can select a more secluded option if you're looking for relaxation.

What’s there to see and do in Annapolis?

While you're exploring the area, Lake Waveland and Rockville Lake Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Turkey Run State Park and Billie Creek Village.

What’s a vacation rental in Annapolis like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Annapolis. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.