Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna
9.4 out of 10, Exceptional, (34)
"Everything was really good. it was clean and well decorated. The only thing is that the yard and landscape needed clean up."
United States
jayne a.
The price is €298
includes taxes & fees
6 Nov - 7 Nov
Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna
This home is located in beautiful Parke County, a rustic and charming setting.
10.0 out of 10, Exceptional, (97)
"Felt like home away from home! Instructions for check in and out were very clear and helpful. Great location to explore the covered bridges or spend the day at Turkey Run. Highly recommend this home."
United States
Tina J.
This home is located in beautiful Parke County, a rustic and charming setting.
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.
2.0 star property
10.0 out of 10, Exceptional, (48)
"Very nice place close to all restaurants stores etc..and only 8 miles from Turkey Run Park!.."
United States
Doug H.
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, (2)
"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!
Millstone Hideaway
9.6 out of 10, Exceptional, (52)
"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
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
10.0 out of 10, Exceptional, (180)
"Great place to stay when visiting parks"
United States
Shannon L.
The price is €195
includes taxes & fees
12 Nov - 13 Nov
Getaway in the country/Beautiful Parke County/Large hot tub and much more!
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly
9.8 out of 10, Exceptional, (47)
"Great location near Shades and Turkey Run! Clean and comfortable, and we loved having access to the game tables in the main area."
United States
Sarah W.
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly
Treetops Cabin in the Woods!
9.8 out of 10, Exceptional, (37)
"Just as advertised. "
United States
anthony t.
Treetops Cabin in the Woods!
Luxury Amish Built Barn Home at Turkey Run
10.0 out of 10, Exceptional, (5)
"The location & setting were great! Close to both Turkey Run & Shades State parks. House is beautiful & worked great for a girls weekend!"
United States
Judi V.
Luxury Amish Built Barn Home at Turkey Run
Charming lake cabin located next to Racoon State Park.
9.2 out of 10, Wonderful, (25)
"We really enjoyed having 2 fire pits and the many different areas to hang out in. For being remote it's easy to get necessities from the local stores. "
United States
Lilliana
Charming lake cabin located next to Racoon State Park.
Quiet and sophisticated apartment with AC in Clinton
10.0 out of 10, Exceptional, (2)
"It was a nice little place to stay. The apartment had everything you need for your stay."
United States
Sarah and Scott C.
Quiet and sophisticated apartment with AC in Clinton
The Getaway House with Hot Tub and Pool. Pet Friendly
9.6 out of 10, Exceptional, (23)
"It's the perfect get away and they where very kind "
United States
Lydia
The Getaway House with Hot Tub and Pool. Pet Friendly
Peaceful and charming apartment in Clinton, Indiana
10.0 out of 10, Exceptional, (2)
"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 €122
includes taxes & fees
4 Nov - 5 Nov
Peaceful and charming apartment in Clinton, Indiana
Cozy lakefront cabin with kayaks
10.0 out of 10, Exceptional, (1)
"Host was very friendly and accessible! Wonderful place to stay!"
United States
Holly R.
Cozy lakefront cabin with kayaks
Secluded in The Woods
9.4 out of 10, Exceptional, (3)
"Clean and well appointed. Would stay here again. "
United States
John & Cathy G.
The price is €161
includes taxes & fees
5 Nov - 6 Nov
Secluded 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!"
United States
Mark C K.
Raccoon Lake Retreat
Nestled near woods and creek, this large home is near state parks and colleges..
10.0 out of 10, Exceptional, (29)
"Great property, we had a wonderful visit!"
United States
Amy M.
Nestled near woods and creek, this large home is near state parks and colleges..
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."
United States
Ted
The price is €214
includes taxes & fees
4 Nov - 5 Nov
1960's Ranch House NO CLEANING FEE
RV Parking and Camping No Hookup
RV Parking and Camping No Hookup
Country living just 4 miles from Crawfordsville
Country living just 4 miles from Crawfordsville
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

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as €122 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna: This holiday home rental outside of Annapolis is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.