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Top Holiday Rentals in Annapolis

Rustic River Cabin Getaway
9.6 out of 10, Exceptional, 58 reviews
"We had a lovely time at the cabin! We stayed for the total eclipse and enjoyed a quiet private viewing in the woods! Our two little dogs were very happy at the property. The road leading down is a little bit rough, but that is the last 3 mile leg of the journey. You can hike up a nearby hill for cell reception if you need to connect, but the best part of this cabin was unplugging and relaxing. The short walk down the road leads to the large gravel riverbank. Fun for fossil hunting, skipping...
Rustic River Cabin Getaway
Hillside Cabin #4 Annapolis, MO Black River
9.6 out of 10, Exceptional, 29 reviews
"Nice new cabin, looks exactly like the pictures. We enjoyed our stay and the host was awesome!"
The price is £221
includes taxes & fees
23 Jun - 24 Jun
Hillside Cabin #4 Annapolis, MO Black River
FS Cabin #1 - 5mins to Black River
The price is £207
includes taxes & fees
4 Jun - 5 Jun
FS Cabin #1 - 5mins to Black River
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Spring Street Cabin #2
9.0 out of 10, Wonderful, 2 reviews
"Plenty of privacy and everything you need. The owner was great at communicating."
The price is £172
includes taxes & fees
16 Jun - 17 Jun
Spring Street Cabin #2
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, 24 reviews
"Really a nice and clean and cozy stay."
The price is £172
includes taxes & fees
4 Jun - 5 Jun
Hillside Cabin #3 Annapolis, MO Black River
Relaxing 3B Cabin-15 min walk to the Black River!
9.6 out of 10, Exceptional, 7 reviews
"We had a family trip with 8 adults and 7 kids, ages from 2 to 16. It was a perfect trip. The cabin had everything you would need for cooking indoors or outside. The kids had a great time playing outside and inside with board games and a huge selection of movies. The adults had a great time catching up together, around the fire and around the dinner table. Loved the decor and the cozy places to sit around in every corner of the cabin. The porch in front with coffee was so nice, listening to the...
Relaxing 3B Cabin-15 min walk to the Black River!
FS Cabin #3 Brand New - 5 mins to Black River
7.6 out of 10, Good, 4 reviews
"Cabin very clean, comfy beds, great kitchen area with nice pots and dishes, cute little porch. Also Thank you Justin for mailing my straightener that I forgot was in bathroom cabinet! Remembered when we were already about hour on road. Overall, highly recommend this great VRBO!"
The price is £156
includes taxes & fees
27 Jun - 28 Jun
FS Cabin #3 Brand New - 5 mins to Black River
Hillside Cabin #2 Annapolis, MO Black River
9.6 out of 10, Exceptional, 54 reviews
"Great !!!!"
The price is £183
includes taxes & fees
4 Jun - 5 Jun
Hillside Cabin #2 Annapolis, MO Black River
Panther Den Cabin is located 4 miles from Hwy K Campground
9.4 out of 10, Exceptional, 10 reviews
"Overall really enjoyed the stay and natural beauty, however not being able to flush toilet paper was definitely a downside"
Panther Den Cabin is located 4 miles from Hwy K Campground
Hillside Cabin #5 Annapolis, MO
10.0 out of 10, Exceptional, 4 reviews
"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"
The price is £177
includes taxes & fees
16 Jun - 17 Jun
Hillside Cabin #5 Annapolis, MO
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
9.8 out of 10, Exceptional, 9 reviews
"We stayed here because of an event we were attending. This was the perfect location for us."
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
Hillside Cabin #1 Annapolis, MO Black River
9.6 out of 10, Exceptional, 35 reviews
"Everything was great, everyone felt comfortable and safe. Everything we needed was there including shampoo, conditioner, and bath soap. We cooked out and used the fire pit, both were great. Everything was clean. We went floating and that was very close. Anything we needed was very close, we wanted for nothing. Highly recommend staying there."
The price is £197
includes taxes & fees
20 Jun - 21 Jun
Hillside Cabin #1 Annapolis, MO Black River
Small Town Lodge - Black River
4.0 out of 10, 1 review
"The bathroom was broken and unusable, we had to skiddaddle first thing in the morning to use the bathroom at the gas station...which was kinda far! OOF. No compensation was made :("
The price is £250
includes taxes & fees
4 Jun - 5 Jun
Small Town Lodge - Black River
FS Cabin #4 - Close to Black River
8.0 out of 10, Very good, 1 review
"We did enjoy staying here. Clean and cozy. Was a little thrown off that it was 20 ft from railroad tracks though."
The price is £159
includes taxes & fees
27 Jun - 28 Jun
FS Cabin #4 - Close to Black River
Micro house cabin located near Silver Mines Recreation Area.
10.0 out of 10, Exceptional, 43 reviews
"From the moment you step out of your vehicle, you feel welcome here. The yard is amazing!! So many amenities and extra activities. The porch is fantastic. The cabin is so well thought out and stocked with necessities. I loved the tile floor and the wood ceilings. The fenced yard is a huge bonus if you travel with pets :) Thank you Shirley, we hope to come again soon!"
Micro house cabin located near Silver Mines Recreation Area.
River front property HOT TUB, Kayak, tubing, and fishing
9.6 out of 10, Exceptional, 70 reviews
"A little difficult to find. Other wise great. "
The price is £221
includes taxes & fees
4 Jun - 5 Jun
River front property HOT TUB, Kayak, tubing, and fishing
Newly remodeled offers many amenities with perfect location!
10.0 out of 10, Exceptional, 13 reviews
"Great location, near all of the local attractions. Very clean and well cared for property. We would definitely stay again. For those who mind, you are directly next to owners private home and neighbors on the other. Although it is rural, you are near others. "
Newly remodeled offers many amenities with perfect location!
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
10.0 out of 10, Exceptional, 4 reviews
"perfect location and very private place."
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
A Place To Relax-Side A
10.0 out of 10, Exceptional, 18 reviews
"This place is such a hidden gem. I was astounded at how well maintained the property was given its size. Absolutely beautiful! It was like stepping back in time to the summer camp in Dirty Dancing! The other side of our cabin was also rented out, but insulation was great, we couldn't even hear the other guests. Everything was cute and comfy and immaculately clean. It stormed (really bad) 2 of our nights and we just sat on the front porch watching, so relaxing. I cannot wait to come back here...
The price is £143
includes taxes & fees
10 Jun - 11 Jun
A Place To Relax-Side A
Rustic Ironton Home w/ Deck & Fire Pit on Creek!
9.8 out of 10, Exceptional, 48 reviews
"Having the creek running near the house was awesome for us. Beds were very comfortable and we felt like we were at home. "
Rustic Ironton Home w/ Deck & Fire Pit on Creek!
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See all available properties in Annapolis
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.

Annapolis Holiday Rental Travel Info

Other types of properties in Annapolis you may be interested in

Rustic River Cabin Getaway
9.6 out of 10, Exceptional, 58 reviews
"We had a lovely time at the cabin! We stayed for the total eclipse and enjoyed a quiet private viewing in the woods! Our two little dogs were very happy at the property. The road leading down is a little bit rough, but that is the last 3 mile leg of the journey. You can hike up a nearby hill for cell reception if you need to connect, but the best part of this cabin was unplugging and relaxing. The short walk down the road leads to the large gravel riverbank. Fun for fossil hunting, skipping...
Rustic River Cabin Getaway
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, 24 reviews
"Really a nice and clean and cozy stay."
The price is £172
includes taxes & fees
4 Jun - 5 Jun
Hillside Cabin #3 Annapolis, MO Black River
Hillside Cabin #4 Annapolis, MO Black River
9.6 out of 10, Exceptional, 29 reviews
"Nice new cabin, looks exactly like the pictures. We enjoyed our stay and the host was awesome!"
The price is £221
includes taxes & fees
23 Jun - 24 Jun
Hillside Cabin #4 Annapolis, MO Black River
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.

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 £143 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 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.

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, K Bridge Recreation Area and Walnut Hollow Lake 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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