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Top Holiday Rentals in Annapolis

Our top choices for Annapolis holiday rentals

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

2.0 star property
10.0 out of 10, Exceptional, (37)
"Would stay again."
Cute, pet-friendly home in quiet neighborhood. Close to state parks & downtown.

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

10.0 out of 10, Exceptional, (177)
"Everything was amazing. Hosts were pleasant and so helpful. Hot tub was perfect after a long day of hiking. "
The price is £166
includes taxes & fees
2 Sept - 3 Sept
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, (31)
"Glad to have a state park pass included. Enjoyed ability to have campfires in the evenings. Cute decor in a vintage house"
The price is £254
includes taxes & fees
8 Sept - 9 Sept
Quaint century-old home just minutes from Turkey Run & Shades State Park w Sauna

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

9.8 out of 10, Exceptional, (41)
"Clean and well maintained."
Quaint Apartment - 10 Min from Turkey Run and Shades, Pet Friendly

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

9.0 out of 10, Wonderful, (14)
"Great location with a beautiful lake view. "
Cozy Lakefront Cabin on Raccoon Lake, near Turkey Run State Park

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!

Treetops Cabin in the Woods!

9.8 out of 10, Exceptional, (36)
"I will book from them every time I go back to Indiana!"
Treetops Cabin in the Woods!

Secluded in The Woods

10.0 out of 10, Exceptional, (2)
"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 £137
includes taxes & fees
3 Sept - 4 Sept
Secluded in The Woods

Cozy lakefront cabin with kayaks

The price is £367
includes taxes & fees
28 Sept - 29 Sept
Cozy lakefront cabin with kayaks

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

10.0 out of 10, Exceptional, (90)
"We enjoyed our stay very much! The home was cute and clean and had everything we needed. If we are ever back in the area this is where we would stay again! "
This home is located in beautiful Parke County, a rustic and charming setting.

Millstone Hideaway

9.6 out of 10, Exceptional, (48)
"Had a great time and the cabin is nestled in the woods. Beautiful and relaxing."
Millstone Hideaway

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, (23)
"Loved the decor and quaintness of cabin and location. "
Charming lake cabin located next to Racoon State Park.

The Getaway House with Hot Tub and Pool. Pet Friendly

9.6 out of 10, Exceptional, (20)
"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

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

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..

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."
The price is £176
includes taxes & fees
2 Sept - 3 Sept
1960's Ranch House NO CLEANING FEE

The Narrows Cabins # 2968

The Narrows Cabins # 2968

The Narrows Cabins - Whispering Wind

The Narrows Cabins - Whispering Wind

The Lodge at The Narrows Cabins

The Lodge at The Narrows Cabins
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

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 £137 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.