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Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
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 vacation 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 AED 918
AED 1,930 total
includes taxes & fees
19 Aug - 20 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, (26 reviews)
"Our stay was great house was clean and in a good location for us "
United States
Randy W.
The price is AED 873
AED 1,016 total
includes taxes & fees
3 Sep - 4 Sep
The Rustic Retreat
Interior

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
9.0 out of 10, Wonderful, (2 reviews)
"Very clean, family friendly, and beautiful cabin."
United States
Rebecca C.
The price is AED 503
AED 1,227 total
includes taxes & fees
25 Aug - 26 Aug
The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!
Exterior

4. The Narrows Cabins - Whispering Wind

The Narrows Cabins - Whispering Wind
Marshall
9.0 out of 10, Wonderful, (2 reviews)
"It is a very cozy cabin for 2 people. You are a very short walk to the trails at Turkey Run."
United States
Michael F.
The price is AED 360
AED 850 total
includes taxes & fees
1 Sep - 2 Sep
The Narrows Cabins - Whispering Wind
Smart TV

5. 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 AED 808
AED 1,037 total
includes taxes & fees
30 Aug - 31 Aug
1960's Ranch House NO CLEANING FEE
TV, fireplace

6. 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 AED 501
AED 834 total
includes taxes & fees
19 Aug - 20 Aug
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Dining

7. 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 AED 404
AED 1,449 total
includes taxes & fees
19 Aug - 20 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

Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

10/10 Excellent
"This was the coolest place we have ever stayed! We like to find unique and different places to stay. This places topped them all! So much thought put into the whole school, not just the apartment. Having access to the lobby game room and the old gymnasium exceeded our expectations. All kinds of school history hung along the walls to learn about the life of the school. I only wish there was more than just one apartment/BNB so we could bring our family to stay there. Close to everything we wanted to do as well. Thank you Mr. Charles. This is one for the books and will never be forgotten!"
Heather K. 2-night trip
Posted 2 days ago
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

Frequently asked questions

Can I find vacation rentals in Annapolis?

Yes, we give you a choice of vacation rentals close to popular attractions in Annapolis, or you can select a more secluded option if you're looking for relaxation.

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

The Rustic Retreat: This vacation home rental outside of Annapolis offers a fireplace, a hot tub, and a barbecue grill 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 larger area, you’ll find Turkey Run State Park and Billie Creek Village.

What’s a vacation rental in Annapolis like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Annapolis. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.