Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Annapolis

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

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

Waveland
10.0 out of 10, Exceptional, (4)
"We enjoyed this space for a multi-generational family reunion. The fire pit and outdoor spaces are phenomenal. "
United States
Tina R.
Sugar Creek Cabin w/ Nordic spa bordering 2 state parks!
TV
Cozy lakefront cabin with kayaks

Cozy lakefront cabin with kayaks

Crawfordsville
10.0 out of 10, Exceptional, (2)
"Host was very friendly and accessible! Wonderful place to stay!"
United States
Holly R.
Cozy lakefront cabin with kayaks
Exterior
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

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

2.0 star property
Rockville
10.0 out of 10, Exceptional, (53)
"Nice location to everything "
United States
Brad B.
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.
Outdoor dining
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

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

Waveland
9.8 out of 10, Exceptional, (49)
"Fantastic unique place. We were very comfortable and had fun exploring the games in the common area. "
United States
Tamara
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly
Fridge, microwave, oven, stovetop
Luxury Amish Built Barn Home at Turkey Run

Luxury Amish Built Barn Home at Turkey Run

Marshall
10.0 out of 10, Exceptional, (7)
"This property was amazing!"
United States
Kate L.
Luxury Amish Built Barn Home at Turkey Run
TV, fireplace
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, (184)
"We came to Rosedale to visit relatives, so not exactly a weekend getaway, but it was so nice to have this place all to ourselves. "
United States
Angel B.
The price is ￥21,175
￥35,056 total
includes taxes & fees
Dec 7 - Dec 8
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Fridge, microwave, oven, stovetop
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.

Rockville
10.0 out of 10, Exceptional, (99)
"Loved the house, so cute. Conveniently located to Turkey Run State Park"
United States
Tonya F.
This home is located in beautiful Parke County, a rustic and charming setting.
3 bedrooms, travel crib, free WiFi, bed sheets
Treetops Cabin in the Woods!

Treetops Cabin in the Woods!

Bloomingdale
9.8 out of 10, Exceptional, (38)
"Beautiful view from cabin. Host communicated well."
United States
Julie P.
Treetops Cabin in the Woods!
Outdoor spa tub
Charming lake cabin located next to Racoon State Park.

Charming lake cabin located next to Racoon State Park.

Rockville
9.2 out of 10, Wonderful, (27)
"Good place to meet with friends with a great location. "
United States
David O.
Charming lake cabin located next to Racoon State Park.
Pool
The Getaway House with Hot Tub and Pool. Pet Friendly

The Getaway House with Hot Tub and Pool. Pet Friendly

Rosedale
9.6 out of 10, Exceptional, (23)
"Great stay, cozy and had everything we needed for us and our dog. "
United States
Nate C.
The Getaway House with Hot Tub and Pool. Pet Friendly
Property grounds
Peaceful and charming apartment in Clinton, Indiana

Peaceful and charming apartment in Clinton, Indiana

Clinton
10.0 out of 10, Exceptional, (3)
"While our stay was short it was a great stay. It is a great location. We attended an event in Rockville and we were able to enjoy our time without the added pressure of a long drive or loud rude neighbors. Thank you for a great time!"
United States
David
The price is ￥11,883
￥21,139 total
includes taxes & fees
Dec 15 - Dec 16
Peaceful and charming apartment in Clinton, Indiana
Fireplace
Millstone Hideaway

Millstone Hideaway

Rockville
9.6 out of 10, Exceptional, (54)
"Great little place in the middle of nowhere exactly what we needed. It's like going to Grandma's summer cabin on the lake. Would definitely stay here again."
United States
Edie D.
Millstone Hideaway
Interior
Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna

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

Marshall
9.4 out of 10, Exceptional, (35)
"It was overall good stay for my family, it’s old fashion but it was good! Just the bathroom had trouble"
United States
Joselle Mae
Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna
Smart TV
Raccoon Lake Retreat

Raccoon Lake Retreat

Rockville
10.0 out of 10, Exceptional, (2)
"This place was very clean and comfortable. The manager, Tawn, is incredible!"
United States
Mark C K.
Raccoon Lake Retreat
3 bedrooms, iron/ironing board, free WiFi, bed sheets
1960's Ranch House NO CLEANING FEE

1960's Ranch House NO CLEANING FEE

Dana
10.0 out of 10, Exceptional, (14)
"Quite, clean property felt very safe and the owner was very nice and quick to respond."
United States
Ted
The price is ￥26,806
￥33,498 total
includes taxes & fees
Dec 9 - Dec 10
1960's Ranch House NO CLEANING FEE
Property grounds
Nestled near woods and creek, this large home is near state parks and colleges..

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

Hillsboro
10.0 out of 10, Exceptional, (29)
"Very large house perfect for family gatherings!"
United States
Mark R.
Nestled near woods and creek, this large home is near state parks and colleges..
Exterior
Secluded in The Woods

Secluded in The Woods

Dana
9.4 out of 10, Exceptional, (3)
"Clean and well appointed. Would stay here again. "
United States
John & Cathy G.
Secluded in The Woods
Microwave, oven, stovetop
Quiet and sophisticated apartment with AC in Clinton

Quiet and sophisticated apartment with AC in Clinton

Clinton
10.0 out of 10, Exceptional, (3)
"Great location, quiet and super clean."
United States
james p.
Quiet and sophisticated apartment with AC in Clinton
Outdoor dining
Country living just 4 miles from Crawfordsville

Country living just 4 miles from Crawfordsville

Crawfordsville
Country living just 4 miles from Crawfordsville
Exterior
The Narrows Cabins #2964

The Narrows Cabins #2964

Marshall
The Narrows Cabins #2964
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

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!

10/10 Excellent
"Easy communication, early arrival accomidations and a beautiful night stay. We enjoyed ourselves a lot!"
Alan C. 1-night trip
Posted 4 days ago
Getaway in the country/Beautiful Parke County/Large hot tub and much more!

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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Look no further and take a look at our great range of rental properties in Annapolis!

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?

Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.: This vacation 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 you can cook with friends or family.

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.