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Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Annapolis holiday rentals

Property grounds

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

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
Marshall
9.4 out of 10, Exceptional, (41 reviews)
"Everything was good. The house had everything needed for our stay and then some. The only thing lacking was an escape access for the upstairs bedrooms in case of a fire or other emergency."
United States
Melanie H.
The price is HK$1,961
HK$4,122 total
includes taxes & fees
24 Aug - 25 Aug
Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
Terrace/patio

2. The Rustic Retreat

The Rustic Retreat
Marshall
10.0 out of 10, Exceptional, (27 reviews)
"Our stay was great house was clean and in a good location for us "
United States
Randy W.
The price is HK$1,863
HK$2,169 total
includes taxes & fees
3 Sept - 4 Sept
The Rustic Retreat
Smart TV

3. 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$1,725
HK$2,214 total
includes taxes & fees
30 Aug - 31 Aug
1960's Ranch House NO CLEANING FEE
TV, fireplace

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, (197 reviews)
"Such a peaceful place to stay!"
United States
Mariah M.
The price is HK$1,070
HK$1,817 total
includes taxes & fees
27 Aug - 28 Aug
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Dining

5. Walk to Dtwn Rockville! Prairie-Inspired Retreat

Walk to Dtwn Rockville! Prairie-Inspired Retreat
Rockville
9.0 out of 10, Wonderful, (2 reviews)
"Fantastic place! Fantastic owner! Easy communication, would stay again!"
United States
Ryan P.
The price is HK$862
HK$3,092 total
includes taxes & fees
30 Aug - 31 Aug
Walk to Dtwn Rockville! Prairie-Inspired Retreat
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
"Great location with very responsive hosts. Very clean and lots of included amenities such as shampoo, conditioner, soaps, tea and coffee. Close to covered bridges, Turkey run state park, and much more. We ate breakfast every morning at Benjamin’s in Rockville. The Reservation in Montezuma on the Wabash river was an excellent place to eat as well as The Ranch located at the entrance of Raccoon State Recreation Area."
Michelle G. 4-night trip
Posted 3 days 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
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • 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: 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, 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.