Annapolis Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Annapolis vacation rentals

Microwave, oven, stovetop
Peaceful and charming apartment in Clinton, Indiana

Peaceful and charming apartment in Clinton, Indiana

Peaceful and charming apartment in Clinton, Indiana
Clinton
10.0 out of 10, Exceptional, (3)
"While our stay was short it was a great stay. It is a great location. We attended an event in Rockville and we were able to enjoy our time without the added pressure of a long drive or loud rude neighbors. Thank you for a great time!"
United States
David
$122 nightly
The price is $136
Dec 22 - Dec 23
Total with taxes and fees
Peaceful and charming apartment in Clinton, Indiana
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!

Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Rosedale
10.0 out of 10, Exceptional, (184)
"We came to Rosedale to visit relatives, so not exactly a weekend getaway, but it was so nice to have this place all to ourselves. "
United States
Angel B.
$197 nightly
The price is $226
Dec 14 - Dec 15
Total with taxes and fees
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Smart TV
1960's Ranch House NO CLEANING FEE

1960's Ranch House NO CLEANING FEE

1960's Ranch House NO CLEANING FEE
Dana
10.0 out of 10, Exceptional, (14)
"Quite, clean property felt very safe and the owner was very nice and quick to respond."
United States
Ted
$212 nightly
The price is $237
Dec 14 - Dec 15
Total with taxes and fees
1960's Ranch House NO CLEANING FEE
Terrace/patio
The Rustic Retreat only 1 mile from Turkey Run State Park

The Rustic Retreat only 1 mile from Turkey Run State Park

The Rustic Retreat only 1 mile from Turkey Run State Park
2.0 star property
Marshall
$164 nightly
The price is $189
Dec 16 - Dec 17
Total with taxes and fees
The Rustic Retreat only 1 mile from Turkey Run State Park
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

Charming lake cabin located next to Racoon State Park.

Charming lake cabin located next to Racoon State Park.

10/10 Excellent
"Location was perfect for the country setting we were looking for. Everything was great no problems at all"
Joshua H. 7-night trip
Posted 4 days ago
Charming lake cabin located next to Racoon State Park.

Find out more about Annapolis

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.: This vacation home rental outside of Annapolis offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 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.