Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

2.0 star property
10.0 out of 10, Exceptional, (35)
"This was a perfect location to spend some time at Turkey Run. The neighborhood was quiet and the host was kind. "
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

Sugar Creek Cabin w/ Nordic spa bordering 2 state parks!

10.0 out of 10, Exceptional, (1)
"We had a very relaxing stay. Property had everything we needed "
Sugar Creek Cabin w/ Nordic spa bordering 2 state parks!

Getaway in the country/Beautiful Parke County/Large hot tub and much more!

10.0 out of 10, Exceptional, (177)
"This is well kept property with super nice hosts. It's perfect for a couples get away. "
The price is NZ$373
includes taxes & fees
3 Aug - 4 Aug
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna

9.4 out of 10, Exceptional, (30)
"The host was amazing and accommodated our needs. They were super quick to respond when I had questions. The house was great! It had everything we could possibly need and was conveniently located close to Turkey Run. Will definitely be back. "
The price is NZ$574
includes taxes & fees
6 Aug - 7 Aug
Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna

Millstone Hideaway

9.6 out of 10, Exceptional, (45)
"Had a great time and the cabin is nestled in the woods. Beautiful and relaxing."
Millstone Hideaway

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

9.8 out of 10, Exceptional, (40)
"Clean and well maintained."
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

The Getaway House with Hot Tub and Pool. Pet Friendly

9.6 out of 10, Exceptional, (18)
"Really enjoyed our stay at this great property in Parke county. The hosts are lovely people who take pride in their property and ensure you have what you need for a relaxing getaway. Location is great to get to all of the area sites via short drives. Love the proximity to Turkey Run state park and many covered bridges.Highly recommend. "
The Getaway House with Hot Tub and Pool. Pet Friendly

Cozy Lakefront Cabin on Raccoon Lake, near Turkey Run State Park

9.4 out of 10, Exceptional, (13)
"Perfect, cant wait to come back! Love the cabin. "
Cozy Lakefront Cabin on Raccoon Lake, near Turkey Run State Park

Cozy lakefront cabin with kayaks

Cozy lakefront cabin with kayaks

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

10.0 out of 10, Exceptional, (87)
"Thank you for the beautiful stay!! "
This home is located in beautiful Parke County, a rustic and charming setting.

A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

10.0 out of 10, Exceptional, (61)
"Everything was perfect! Spent all our time there on the back deck. "
The price is NZ$520
includes taxes & fees
21 Aug - 22 Aug
A Cozy, relaxing hideaway! 1/2 a mile from Billie Creek Covered Bridge.

Treetops Cabin in the Woods!

9.8 out of 10, Exceptional, (35)
"We had a great time staying at The TreeTops. Beautiful home in wooded setting. Upper room grabbed by our teen and we slept in larger room. Loved the porch both indoor and outdoor. Grilled overlooking wooded drop off. Saw wildlife including a turkey. Excellent location only 15 minutes from Turkey Run Stste Psrk. Ate at wooden table in entry area and played games there as well. House well stocked. Would definitely rent again!"
Treetops Cabin in the Woods!

Raccoon Lake Retreat

10.0 out of 10, Exceptional, (2)
"This place was very clean and comfortable. The manager, Tawn, is incredible!"
Raccoon Lake Retreat

Charming lake cabin located next to Racoon State Park.

9.2 out of 10, Wonderful, (22)
"Loved the decor and quaintness of cabin and location. "
Charming lake cabin located next to Racoon State Park.

Nestled near woods and creek, this large home is near state parks and colleges..

10.0 out of 10, Exceptional, (26)
"Everything was wonderful "
Nestled near woods and creek, this large home is near state parks and colleges..

Luxury Amish Built Barn Home at Turkey Run

10.0 out of 10, Exceptional, (3)
"The location & setting were great! Close to both Turkey Run & Shades State parks. House is beautiful & worked great for a girls weekend!"
Luxury Amish Built Barn Home at Turkey Run

Secluded in The Woods

10.0 out of 10, Exceptional, (1)
"What a lovey place. Kevin is a wonderful host. It was SO clean, which is my #1 priority always, so I was happy with it. The bed was super comfortable. The surroundings are beautiful. "
The price is NZ$304
includes taxes & fees
4 Aug - 5 Aug
Secluded in The Woods

1960's Ranch House NO CLEANING FEE

10.0 out of 10, Exceptional, (14)
"Quite, clean property felt very safe and the owner was very nice and quick to respond."
1960's Ranch House NO CLEANING FEE

Greencastle Tiny House, Walk to Raccoon Lake!

2.0 out of 10, (1)
"There was no Cable, or WIFI as stated in the listing. There was not running water as stated in the listing. The heating/AC unit was very poor and did not keep the house warm. There was dog hair all over the place, yet the listing stated pet free. There were leaks on the walls with brown streaks running down the walls that had not been tended to. The linens smelled as if they had not been washed. There were dead bugs all over the walls and windows in the bathroom. The bathroom and bedroom windows...
Greencastle Tiny House, Walk to Raccoon Lake!

RV Parking and Camping No Hookup

RV Parking and Camping No Hookup
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

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?

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.: This holiday home rental outside of Annapolis offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.