Annapolis Holiday Rentals from AU$311: Search Short-Term Rentals

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Holiday Rentals in Annapolis

"My husband and I came here with the hopes of escaping and just enjoying a peaceful weekend. The cabin is perfect for what we needed. Cozy and comfy and just what we needed. Yes the couch is broken, LOL. But if a broken couch is going to ruin your vacay maybe this isn’t the place for you. Just saying that just added to the character and provided some laughter. "

includes taxes & fees

12 Jan - 13 Jan

"Really a nice and clean and cozy stay."

includes taxes & fees

16 Jan - 17 Jan

"We loved the cabin, it was clean and well kept. Google maps led us astray, but I called the owner and she got us right there. I loved the location, but wish it wasn’t such a long gravel road to get there. I’ll still go back anyway!"

"Enjoyed setting on the deck and not havig to worry about bringing anything but your food and personal items and just relax .internet was in and out , but was fine, aome "

includes taxes & fees

16 Jan - 17 Jan

"There were just some minor things like not being able to find the wifi, a few bugs, and the no cold water for the washer. Other than that, it was comfortable and quiet. I can see myself staying there again"

includes taxes & fees

12 Jan - 13 Jan

"Very convenient for nearby activities. Very clean, great kitchen, very nice bedding and towels better than most hotels. Efficient HVAC. Perimeter could be spruced up. Better mowing, rock in driveway, marking of property. Excellent interior, however, for the price"

includes taxes & fees

12 Jan - 13 Jan

"We arrive to a good-looking cabin in a beautiful location. The check-in instructions were clear and delivered rapidly. It was easy to get inside. We did enjoy sitting on the porch and watching the wildlife. Unfortunately, the problems started soon after. We discovered old, rotting bacon in the microwave. We tried to use the satellite TV service. It did not work, saying all channels were unavailable. We then decided to try the jetted tub. Started putting water in and realized it was not...

"Had a hard time finding, because I forgot to read your instructions. Oops! But found it and was easy to get in. The trains in the evening where intersting to watch do maintenance. We enjoyed a couple new places to eat Thee Abbeys, and Iron Mule. Did Joe's canoe on the black River. Weather ended up being GREAT! Also did Elephant Rock and Johnsons shut-in. Perfect weekend! Johnsons Shut-In. Perfect little enhoyedCa a"

includes taxes & fees

12 Jan - 13 Jan

Fridge, microwave, oven, coffee/tea maker

"I was pretty disappointed with my experience. We booked and paid for this stay up front. The Tuesday before our stay the host told us the unit was being repaired and that it might not be done for our Friday night stay. We were not contacted prior to this. Turns out the property would be completed and we could still come for our stay. I appreciated the communication up until that point. When we arrived the unit seemed ready. However, there was no central air. There was a window unit in the...

includes taxes & fees

12 Jan - 13 Jan

"Pictures where deceiving- counter tops in kitchen only about 26” tall-entire facility was dirty with many cob webs"

includes taxes & fees

12 Jan - 13 Jan

"There was a boil water in effect which is understandable. I boiled water for cooking and dishes. The biggest problem was there was no hot water at. So bathing was a issue. all "

"It was cozy. Have a little trouble getting the place warm at first. But overall comfortable and cozy. Kitchen could use a little more supplies for everyday life especially if you are planning to cook a lot in the kitchen. Shower had no cold water. So the shower was very hot. All that aside was very comfortable and cozy and great for what we needed it for."

includes taxes & fees

12 Jan - 13 Jan

"Our little family really enjoyed our stay at this cabin. It was perfect and had everything we needed to cook with. Will definitely be revisiting. "

includes taxes & fees

12 Jan - 13 Jan

"Family of 5; we all loved it! Kids even unplugged & spent time w/ the grownups! Robin communicated to us about an issue prior to arrival, but it was all fixed and we had no troubles. Loved that the cabin is away from other homes. Beautiful setting. Cows weren't any trouble, didn't have smells either and they were in the pasture. Possibly because it's November. I didn't see mixing bowls or a wire whisk, but everything else was supplied. Wonderful selection of videos & games. Great weekend;...

"Great weekend "

includes taxes & fees

16 Jan - 17 Jan

"Our family rented Bluebird Meadows for a weekend get away. We had a great time all three days. Place was everything we were hoping. "

"We stayed over Thanksgiving. Katie was kind and found local restaurants that would be open. The cabin was decorated for Christmas, cute and cozy. We were slightly disappointed the lake in the pictures was not on the property. "

includes taxes & fees

16 Jan - 17 Jan

"Traveling with a large family is never easy, but this rental made us feel at home. Full kitchen for cooking, dining area to seat everyone, huge tv, great wi-fi, washer and dryer, fun backyard to make s’mores, and beds upstairs to sleep all our kids. We would stay here again!"

includes taxes & fees

14 Jan - 15 Jan

"Great accommodations for a family, lots of room. No wifi, tho."

"Loved staying a week at Sunshine Shack. The screened in deck is perfect to watch the deer at dusk."

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Other types of properties in Annapolis you may be interested in

"Really a nice and clean and cozy stay."

includes taxes & fees

16 Jan - 17 Jan

"My husband and I came here with the hopes of escaping and just enjoying a peaceful weekend. The cabin is perfect for what we needed. Cozy and comfy and just what we needed. Yes the couch is broken, LOL. But if a broken couch is going to ruin your vacay maybe this isn’t the place for you. Just saying that just added to the character and provided some laughter. "

includes taxes & fees

12 Jan - 13 Jan

"We loved the cabin, it was clean and well kept. Google maps led us astray, but I called the owner and she got us right there. I loved the location, but wish it wasn’t such a long gravel road to get there. I’ll still go back anyway!"

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, 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 favourite 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 depend 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 AU$311 per night. Entering your travel dates in the search wizard might find you 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.

Annapolis Holiday Home Travel Info

Number of holiday homes	4
Popular accommodation	Annapolis private holiday homes
Known landmarks	K Bridge Recreation Area, Walnut Hollow Lake and Crane Lake Recreation Area
International airport	St. Louis, MO (STL-Lambert-St. Louis Intl.)

Recent reviews of Annapolis properties

5/5 Excellent

"The price was reasonable and very comfortable ."

A verified traveller stayed at Shepherd Mountain Inn

Posted 1 month ago

4/5 Good

Comfortable and cozy

"It was cozy. Have a little trouble getting the place warm at first. But overall comfortable and cozy. Kitchen could use a little more supplies for everyday life especially if you are planning to cook a lot in the kitchen. Shower had no cold water. So the shower was very hot. All that aside was very comfortable and cozy and great for what we needed it for."

A verified traveller stayed at Small Town Lodge - Black River

Posted 2 months ago

Relaxing 3B Cabin-15 min walk to the Black River!

2/5 Poor

I hate leaving negative reviews, but...

"We arrive to a good-looking cabin in a beautiful location. The check-in instructions were clear and delivered rapidly. It was easy to get inside. We did enjoy sitting on the porch and watching the wildlife. Unfortunately, the problems started soon after. We discovered old, rotting bacon in the microwave. We tried to use the satellite TV service. It did not work, saying all channels were unavailable. We then decided to try the jetted tub. Started putting water in and realized it was not draining. Pulled the drain out and cleaned out two large clumps of someone's hair. That got it to drain, so I cleaned it and tried filling it again. On top of the water coming in, it also had lots of black floating material which appeared to be mold. Skipped the tub. Played a round of yahtzee and called it a night. We slept in and, when we woke in the late morning on my wife's birthday, we went to town to try to get her a cake. Upon our return, we discovered two roaches on the kitchen floor. It's pretty clear that cleaning is not a priority here. At this point, we'd had enough and decided to pack up and leave. It was 1pm, a couple hours after the 11am check-out time, when we messaged the host to tell him we were leaving and why. I expected some sort of reasonable response and maybe a partial refund offer since we were only 2 hours past check-out, but only got a "I'll inspect the cabin. Sorry for the inconvenience" and "I'll let the cleaners know." First bad VRBO experience. One ruined b-day."

A verified traveller stayed at Relaxing 3B Cabin-15 min walk to the Black River!

Posted 2 months ago

Hillside Cabin #2 Annapolis, MO Black River

5/5 Excellent

Perfect Peaceful Getaway

"My husband and I came here with the hopes of escaping and just enjoying a peaceful weekend. The cabin is perfect for what we needed. Cozy and comfy and just what we needed. Yes the couch is broken, LOL. But if a broken couch is going to ruin your vacay maybe this isn’t the place for you. Just saying that just added to the character and provided some laughter. "

A verified traveller stayed at Hillside Cabin #2 Annapolis, MO Black River

Posted 3 months ago

5/5 Excellent

I would love to go back!!

"We loved the cabin, it was clean and well kept. Google maps led us astray, but I called the owner and she got us right there. I loved the location, but wish it wasn’t such a long gravel road to get there. I’ll still go back anyway!"

A verified traveller stayed at Rustic River Cabin Getaway

Posted 4 months ago

Frequently asked questions

Can I find a holiday rental 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. Annapolis is known for its riverfront and parks. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Annapolis has to offer?

7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont : This highly rated holiday home rental in Annapolis is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Annapolis is Spring Street Cabin #2.

How many holiday rentals are there in Annapolis?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Annapolis stay.

What can I see and do in Annapolis?

Taum Sauk Mountain State Park and Mark Twain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, Walnut Hollow Lake and K Bridge Recreation Area are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.

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Annapolis Holiday Rentals

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Check Annapolis holiday rental availability

Holiday Rentals in Annapolis

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River

Rustic River Cabin Getaway

Rustic River Cabin Getaway

Hillside Cabin #4 Annapolis, MO Black River

Hillside Cabin #4 Annapolis, MO Black River

FS Cabin #1 - 5mins to Black River

FS Cabin #1 - 5mins to Black River

Hillside Cabin #5 Annapolis, MO

Hillside Cabin #5 Annapolis, MO

Relaxing 3B Cabin-15 min walk to the Black River!

Relaxing 3B Cabin-15 min walk to the Black River!

FS Cabin #3 Brand New - 5 mins to Black River

FS Cabin #3 Brand New - 5 mins to Black River

Spring Street Cabin #2

Spring Street Cabin #2

Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River

Panther Den Cabin is located 4 miles from Hwy K Campground

Panther Den Cabin is located 4 miles from Hwy K Campground

Small Town Lodge - Black River

Small Town Lodge - Black River

FS Cabin #4 - Close to Black River

FS Cabin #4 - Close to Black River

Secluded Log Cabin - Total privacy

Secluded Log Cabin - Total privacy

River front property HOT TUB, Kayak, tubing, and fishing

River front property HOT TUB, Kayak, tubing, and fishing

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!

Enjoy a charming 1860s newly renovated home!!

Enjoy a charming 1860s newly renovated home!!

Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Sunshine Shack at Clearwater Lake (sleeps 6)

Sunshine Shack at Clearwater Lake (sleeps 6)

Other types of properties in Annapolis you may be interested in

Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

Rustic River Cabin Getaway

Rustic River Cabin Getaway

Find out more about Annapolis

Find out more about Annapolis

Annapolis Holiday Home Travel Info

Recent reviews of Annapolis properties

Recent reviews of Annapolis properties

Shepherd Mountain Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions