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Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Annapolis holiday rentals

A rustic cabin with a wooden exterior, a porch, and a mailbox.

1. The Narrows Cabins # 2968

The Narrows Cabins # 2968
Marshall
10.0 out of 10, Exceptional, (3 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 HK$918
HK$2,165 total
includes taxes & fees
9 Nov - 10 Nov
The Narrows Cabins # 2968
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 HK$1,176
HK$3,008 total
includes taxes & fees
1 Nov - 2 Nov
Walk to Dtwn Rockville! Prairie-inspired Retreat
Cozy cabin retreat with fire pit, grill, and serene wooded yard

3. The Twilight at The Narrows Cabins

The Twilight at The Narrows Cabins
Marshall
The price is HK$1,121
HK$2,507 total
includes taxes & fees
28 Oct - 29 Oct
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
8.6 out of 10, Excellent, (4 reviews)
"Great house for our short (one night) stay while traveling through. Easy to find and very clean."
United States
Joan P.
The price is HK$863
HK$3,093 total
includes taxes & fees
1 Nov - 2 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 HK$1,059
HK$2,940 total
includes taxes & fees
27 Oct - 28 Oct
The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!
A rustic log cabin with a porch, surrounded by trees and a gravel area with outdoor seating.

6. 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 HK$839
HK$2,110 total
includes taxes & fees
17 Nov - 18 Nov
The Narrows Cabins #2962 - The Nook
A cozy living room with a wooden floor, a sofa, a coffee table, and a dining table with chairs.

7. 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 HK$1,071
HK$1,808 total
includes taxes & fees
27 Oct - 28 Oct
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
A cabin with a fire pit, outdoor seating, and string lights.

8. 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 HK$2,047
HK$4,239 total
includes taxes & fees
17 Nov - 18 Nov
Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
A wooden cabin with a porch, a picnic table, and a mailbox.

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 HK$816
HK$2,092 total
includes taxes & fees
27 Oct - 28 Oct
The Narrows Cabins #2960 - The Nest
A wooden cabin with a porch, a bench, and a mailbox.

10. 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 HK$847
HK$2,778 total
includes taxes & fees
27 Oct - 28 Oct
The Narrows Cabins #2966
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.

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 HK$1,004
HK$2,868 total
includes taxes & fees
17 Nov - 18 Nov
The Narrows Cabins #2964
Cozy cabin with wraparound deck, hot tub, and peaceful wooded lawn

12. The Moonwalk at The Narrows Cabins

The Moonwalk at The Narrows Cabins
Marshall
The price is HK$1,176
HK$3,075 total
includes taxes & fees
4 Nov - 5 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 HK$1,914
HK$2,415 total
includes taxes & fees
16 Nov - 17 Nov
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

This home is located in beautiful Parke County, a rustic and charming setting.

This home is located in beautiful Parke County, a rustic and charming setting.

10/10 Excellent
"The property is even better in person than the photos. Every detail of what a guest needs has been considered. From blankets in the living room, different sized mugs, just wonderful."
Megan L. 2-night trip
Posted 11 hours ago
This home is located in beautiful Parke County, a rustic and charming setting.

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
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  • 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 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.