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
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Annapolis vacation rentals

Terrace/patio

The Rustic Retreat

The Rustic Retreat
Marshall
10.0 out of 10, Exceptional, (12 reviews)
"Great place! "
United States
Scott B.
The price is ￥31,882
￥36,648 total
includes taxes & fees
May 4 - May 5
The Rustic Retreat
Exterior detail

Sleeps 12 • Sauna • Firepit • Minutes to Turkey Run

Sleeps 12 • Sauna • Firepit • Minutes to Turkey Run
Marshall
9.4 out of 10, Exceptional, (36 reviews)
"We were thrilled with this homey getaway! "
United States
Deb J.
The price is ￥28,694
￥79,562 total
includes taxes & fees
May 7 - May 8
Sleeps 12 • Sauna • Firepit • Minutes to Turkey Run
TV, fireplace

Getaway in the country/Beautiful Parke County/Large hot tub and much more!

Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Rosedale
10.0 out of 10, Exceptional, (188 reviews)
"Great host and great stay!"
United States
Dean L.
The price is ￥21,759
￥36,023 total
includes taxes & fees
May 5 - May 6
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Exterior

Secluded in The Woods

Secluded in The Woods
Dana
9.4 out of 10, Exceptional, (3 reviews)
"Clean and well appointed. Would stay here again. "
United States
John & Cathy G.
The price is ￥22,822
￥29,134 total
includes taxes & fees
Apr 30 - May 1
Secluded in The Woods
Smart TV

1960's Ranch House NO CLEANING FEE

1960's Ranch House NO CLEANING FEE
Dana
10.0 out of 10, Exceptional, (14 reviews)
"Quite, clean property felt very safe and the owner was very nice and quick to respond."
United States
Ted
The price is ￥36,824
￥46,599 total
includes taxes & fees
May 10 - May 11
1960's Ranch House NO CLEANING FEE
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis Hotel Reviews

The Getaway House with Hot Tub and Pool. Pet Friendly

The Getaway House with Hot Tub and Pool. Pet Friendly

8/10 Good
"Great location not far from Rockville and Turkey Run State Park. Clean property and appreciated it being pet friendly to bring our 18 pound Maltipoo to enjoy a short vacation! Hot tub was excellent and nice fire pit outdoors with wood provided by owners. Be careful if u have small dog as ours was able to crawl thru openings in fence next to the roadway. Thankfully we got Milo back in quickly! Communication was excellent and got to meet Tony and Lisa in person. Well equipped kitchen and nice rural setting. Would recommend! "
Kevin S. 2-night trip
Posted 1 day ago
The Getaway House with Hot Tub and Pool. Pet Friendly

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 are some of the best vacation rentals that Annapolis has to offer?

The Getaway House with Hot Tub and Pool. Pet Friendly: This vacation home rental outside of Annapolis has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Annapolis?

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

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.