Annapolis Holiday Rentals

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Check prices for these dates

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

Our top choices for Annapolis holiday rentals

A rustic log cabin with a porch, surrounded by trees and a gravel area with outdoor seating.

1. The Narrows Cabins #2962 - The Nook

The Narrows Cabins #2962 - The Nook
Marshall
10.0 out of 10, Exceptional, (2 reviews)
"Great stay! Cute & so close to Turkey Run. Will be coming back soon."
United States
Hannah C.
The price is AU$366
includes taxes & fees
9 Dec - 10 Dec
The Narrows Cabins #2962 - The Nook
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.

2. Walk to Dtwn Rockville! Prairie-inspired Retreat

Walk to Dtwn Rockville! Prairie-inspired Retreat
3.0 star property
Rockville
The price is AU$559
includes taxes & fees
10 Nov - 11 Nov
Walk to Dtwn Rockville! Prairie-inspired Retreat
A spacious living area with a wooden ceiling, a brown leather sofa, a round wooden coffee table, and a blue armchair.

3. The Twilight at The Narrows Cabins

The Twilight at The Narrows Cabins
Marshall
The price is AU$448
includes taxes & fees
9 Dec - 10 Dec
The Twilight at The Narrows Cabins
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.

4. Walk to Dtwn Rockville! Prairie-Inspired Retreat

Walk to Dtwn Rockville! Prairie-Inspired Retreat
Rockville
8.8 out of 10, Excellent, (6 reviews)
"Fantastic place! Fantastic owner! Easy communication, would stay again!"
United States
Ryan P.
The price is AU$522
includes taxes & fees
10 Nov - 11 Nov
Walk to Dtwn Rockville! Prairie-Inspired Retreat
A wooden cabin interior with a kitchen, dining area, and seating.

5. The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!

The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!
Marshall
9.6 out of 10, Exceptional, (4 reviews)
"Great place to stay!"
United States
B Peter K.
The price is AU$519
includes taxes & fees
9 Dec - 10 Dec
The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!
A wooden cabin with a porch, a bench, and a mailbox.

6. The Narrows Cabins #2966

The Narrows Cabins #2966
Marshall
10.0 out of 10, Exceptional, (2 reviews)
"Great experience for fall break!"
United States
Chelsea H.
The price is AU$478
includes taxes & fees
8 Dec - 9 Dec
The Narrows Cabins #2966
A wooden cabin with a porch, a picnic table, and a mailbox.

7. The Narrows Cabins #2960 - The Nest

The Narrows Cabins #2960 - The Nest
Marshall
9.8 out of 10, Exceptional, (7 reviews)
"Very much enjoyed our stay! It was cute, clean and quiet. Being located so close to the turkey run state park was an added bonus. We’d definitely stay again if back in the area."
United States
Lisa P.
The price is AU$356
includes taxes & fees
8 Dec - 9 Dec
The Narrows Cabins #2960 - The Nest
A rustic cabin with a porch, surrounded by trees and string lights.

8. The Narrows Cabins # 2968

The Narrows Cabins # 2968
Marshall
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed a relaxing weekend in this clean, comfortable cabin. It was within walking distance of hiking trails which was convenient. Close to kayaking, restaurants and delicious ice cream!"
United States
julie k.
The price is AU$386
includes taxes & fees
9 Dec - 10 Dec
The Narrows Cabins # 2968
A cozy living room with a wooden floor, a sofa, a coffee table, and a dining table with chairs.

9. 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, (200 reviews)
"Great place off the beaten path. Clean with great amenities. I would definitely stay here again."
United States
Bridget B.
The price is AU$323
includes taxes & fees
12 Nov - 13 Nov
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
A compact kitchen with a refrigerator, microwave, and wooden cabinets. There is a dining area with a table and chairs, and a small seating area with a sofa and a lamp.

10. The Narrows Cabins #2964

The Narrows Cabins #2964
Marshall
10.0 out of 10, Exceptional, (5 reviews)
"Lovely, clean little place super close to the entrance of Turkey Run state park. Beds were very comfy and a/c worked great. It would have been difficult, however, for more than 3 people as we had to use the top bunk for our suitcases. Otherwise, they would have to be on the living room floor and be in the way. Absolutely no floor space exists in the bedroom except to navigate to the bed."
United States
Denise K.
The price is AU$503
includes taxes & fees
9 Dec - 10 Dec
The Narrows Cabins #2964
A cabin with a fire pit, outdoor seating, and string lights.

11. Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
Marshall
9.4 out of 10, Exceptional, (44 reviews)
"We were thrilled with this homey getaway! "
United States
Deb J.
The price is AU$771
includes taxes & fees
1 Dec - 2 Dec
Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
A bedroom with a bed, a ceiling fan, an air conditioning unit, a window with curtains, and a view of the outdoors.

12. The Moonwalk at The Narrows Cabins

The Moonwalk at The Narrows Cabins
Marshall
The price is AU$559
includes taxes & fees
10 Nov - 11 Nov
The Moonwalk at The Narrows Cabins
A modern living room with a flat-screen TV, two blue armchairs, a grey sofa, and a coffee table.

13. 1960's Ranch House NO CLEANING FEE

1960's Ranch House NO CLEANING FEE
Dana
10.0 out of 10, Exceptional, (16 reviews)
"Great stay and would definitely recommend. Quiet neighborhood with very good local cafe and interesting Ernie Pyle museum. We would stay here again!"
United States
Bernadette J.
The price is AU$427
includes taxes & fees
6 Dec - 7 Dec
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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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 favourite 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 depend 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 AU$322 per night. Entering your travel dates in the search wizard might find you 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 - 1 mile from Turkey Run State Park: This holiday home rental outside of Annapolis offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 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.