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Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

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 NZ$453
includes taxes & fees
4 Nov - 5 Nov
The Narrows Cabins #2962 - The Nook

2. Walk to Dtwn Rockville! Prairie-inspired Retreat

Walk to Dtwn Rockville! Prairie-inspired Retreat
3.0 star property
Rockville
The price is NZ$681
includes taxes & fees
3 Nov - 4 Nov
Walk to Dtwn Rockville! Prairie-inspired Retreat

3. 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 NZ$603
includes taxes & fees
9 Nov - 10 Nov
The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!

4. 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 NZ$385
includes taxes & fees
1 Nov - 2 Nov
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

5. Walk to Dtwn Rockville! Prairie-Inspired Retreat

Walk to Dtwn Rockville! Prairie-Inspired Retreat
Rockville
8.8 out of 10, Excellent, (5 reviews)
The price is NZ$649
includes taxes & fees
1 Nov - 2 Nov
Walk to Dtwn Rockville! Prairie-Inspired Retreat

6. The Twilight at The Narrows Cabins

The Twilight at The Narrows Cabins
Marshall
The price is NZ$552
includes taxes & fees
1 Dec - 2 Dec
The Twilight at The Narrows Cabins

7. 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 NZ$601
includes taxes & fees
1 Dec - 2 Dec
The Narrows Cabins #2966

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 NZ$488
includes taxes & fees
1 Dec - 2 Dec
The Narrows Cabins # 2968

9. 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 NZ$429
includes taxes & fees
1 Nov - 2 Nov
The Narrows Cabins #2960 - The Nest

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

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
Marshall
9.4 out of 10, Exceptional, (43 reviews)
"We were thrilled with this homey getaway! "
United States
Deb J.
The price is NZ$890
includes taxes & fees
23 Nov - 24 Nov
Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12

11. The Narrows Cabins #2964

The Narrows Cabins #2964
Marshall
10.0 out of 10, Exceptional, (4 reviews)
"Very impressed with the well stocked items including coffee, Tide pods, ice in the freezer, bug spray and even soft toilet paper. Comfortable and clean."
United States
April D.
The price is NZ$612
includes taxes & fees
17 Nov - 18 Nov
The Narrows Cabins #2964

12. The Cottage at The Narrows Cabins

The Cottage at The Narrows Cabins
Marshall
9.6 out of 10, Exceptional, (4 reviews)
"Had a relaxing stay and things were clean."
United States
Abraham W.
The price is NZ$1,401
includes taxes & fees
8 Nov - 9 Nov
The Cottage at The Narrows Cabins

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 NZ$503
includes taxes & fees
16 Nov - 17 Nov
1960's Ranch House NO CLEANING FEE

14. The Moonwalk at The Narrows Cabins

The Moonwalk at The Narrows Cabins
Marshall
The price is NZ$744
includes taxes & fees
4 Nov - 5 Nov
The Moonwalk at The Narrows Cabins
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Annapolis holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Annapolis. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Annapolis. Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Annapolis short-term rentals, that won’t be hard to do.

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.