Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

Under Renovation for an even bigger & better experience! We’re so excited!

Under Renovation for an even bigger & better experience! We’re so excited!
Marshall
9.4 out of 10, Exceptional, (36 reviews)
"We were thrilled with this homey getaway! "
United States
Deb J.
The price is NZ$672
includes taxes & fees
16 Feb - 17 Feb
Under Renovation for an even bigger & better experience! We’re so excited!

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, (185 reviews)
"It was clean and just what we needed for rest. We would definitely return if ever back in the area"
United States
Jeff R.
The price is NZ$377
includes taxes & fees
1 Feb - 2 Feb
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

The Rustic Retreat only 1 mile from Turkey Run State Park

The Rustic Retreat only 1 mile from Turkey Run State Park
Marshall
10.0 out of 10, Exceptional, (2 reviews)
"Great place! "
United States
Scott B.
The price is NZ$311
includes taxes & fees
4 Feb - 5 Feb
The Rustic Retreat only 1 mile from Turkey Run State Park

The Getaway House with Hot Tub and Pool. Pet Friendly

The Getaway House with Hot Tub and Pool. Pet Friendly
Rosedale
9.6 out of 10, Exceptional, (23 reviews)
"Great location half between Terre Haute and Turkey Run. The hot tub was phenomenal!!!"
United States
Toni D.
The price is NZ$487
includes taxes & fees
1 Feb - 2 Feb
The Getaway House with Hot Tub and Pool. Pet Friendly

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.
Secluded in The Woods

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 NZ$399
includes taxes & fees
1 Feb - 2 Feb
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.
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Top Annapolis Hotel Reviews

Find out more about Annapolis

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annapolis holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as NZ$377 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Annapolis?

Yes, there are holiday rentals close to the most popular sights in Annapolis, or you can select a more secluded option if you're looking for a relaxing stay.

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

The Rustic Retreat only 1 mile from Turkey Run State Park: This holiday home rental outside of Annapolis has air conditioning and laundry facilities 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 wider area, you’ll find Turkey Run State Park and Billie Creek Village.

What’s a holiday rental in Annapolis like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Annapolis. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.