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Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

The Narrows Cabins - Whispering Wind

The Narrows Cabins - Whispering Wind
Marshall
8.0 out of 10, Very good, (1 review)
"This is a super little cabin! The only issue was the outside chairs were very “rustic”… and very uncomfortable to sit more than a few minutes. Not great for sitting around a camp fire. The other cabin had new chairs outside and even more inside that weren’t even used. Wish it would have been noted in the listing to bring camp chairs. Outside of this is was a great place to stay for a get away."
United States
Sally G.
The price is CA $142
CA $373 total
includes taxes & fees
Jul 28 - Jul 29
The Narrows Cabins - Whispering Wind

The Narrows Cabins #2962 - The Nook

The Narrows Cabins #2962 - The Nook
Marshall
The price is CA $144
CA $374 total
includes taxes & fees
Aug 18 - Aug 19
The Narrows Cabins #2962 - The Nook

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
8.0 out of 10, Very good, (1 review)
"Please print the property guide out and put a copy of your checkout rules on the wall or leave it on the table to make it easier for us to know what your expectations are. It was hard for me to get messages and find the link for the property guide while we were out there. I ended up with about five different emails to look through to find which one had the link, then on one link it did not work. I don’t want to use QR CODES and my phone for a policy guide. I’m trying to get AWAY from technology...
United States
Lisa I.
The price is CA $231
CA $565 total
includes taxes & fees
Aug 10 - Aug 11
The Stargazer! A cozy cabin near Turkey Run State Park! Pet friendly!

The Rustic Retreat

The Rustic Retreat
Marshall
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was great house was clean and in a good location for us "
United States
Randy W.
The Rustic Retreat

The Narrows Cabins # 2968

The Narrows Cabins # 2968
Marshall
The price is CA $154
CA $377 total
includes taxes & fees
Aug 18 - Aug 19
The Narrows Cabins # 2968

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12

Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12
Marshall
9.4 out of 10, Exceptional, (40 reviews)
"We were thrilled with this homey getaway! "
United States
Deb J.
The price is CA $415
CA $811 total
includes taxes & fees
Aug 24 - Aug 25
Turkey Run Retreat - Fire Pit - Sauna - Sleeps 12

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, (195 reviews)
"Such a peaceful place to stay!"
United States
Mariah M.
The price is CA $192
CA $326 total
includes taxes & fees
Jul 30 - Jul 31
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

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 CA $325
CA $415 total
includes taxes & fees
Aug 12 - Aug 13
1960's Ranch House NO CLEANING FEE

Walk to Dtwn Rockville! Prairie-Inspired Retreat

Walk to Dtwn Rockville! Prairie-Inspired Retreat
Rockville
The price is CA $155
CA $554 total
includes taxes & fees
Jul 26 - Jul 27
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

Find out more about Annapolis

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.