Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Exterior
Hillside Cabin #4 Annapolis, MO Black River
9.6 out of 10, Exceptional, (29)
"Nice new cabin, looks exactly like the pictures. We enjoyed our stay and the host was awesome!"
The price is NZ$448
includes taxes & fees
23 Jun - 24 Jun
Hillside Cabin #4 Annapolis, MO Black River
Exterior
Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (58)
"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
Fridge, microwave, oven, stovetop
FS Cabin #1 - 5mins to Black River
The price is NZ$421
includes taxes & fees
28 May - 29 May
FS Cabin #1 - 5mins to Black River
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Fridge, microwave, oven, stovetop
Hillside Cabin #5 Annapolis, MO
10.0 out of 10, Exceptional, (3)
"Absolutely lovely! Close to the Black River, which was where we floated. It was a very nice cabin"
The price is NZ$361
includes taxes & fees
28 May - 29 May
Hillside Cabin #5 Annapolis, MO
Outdoor dining
Relaxing 3B Cabin-15 min walk to the Black River!
9.6 out of 10, Exceptional, (7)
"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!
Fridge, microwave, oven, stovetop
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, (24)
"Really a nice and clean and cozy stay."
The price is NZ$351
includes taxes & fees
28 May - 29 May
Hillside Cabin #3 Annapolis, MO Black River
Outdoor dining
FS Cabin #3 Brand New - 5 mins to Black River
7.6 out of 10, Good, (4)
"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 NZ$318
includes taxes & fees
27 Jun - 28 Jun
FS Cabin #3 Brand New - 5 mins to Black River
1 bedroom, free WiFi, bed sheets
Panther Den Cabin is located 4 miles from Hwy K Campground
9.4 out of 10, Exceptional, (10)
"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
Property grounds
Hillside Cabin #2 Annapolis, MO Black River
9.6 out of 10, Exceptional, (54)
"Great !!!!"
The price is NZ$372
includes taxes & fees
28 May - 29 May
Hillside Cabin #2 Annapolis, MO Black River
Property grounds
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
9.8 out of 10, Exceptional, (9)
"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
Fridge, microwave, oven, coffee/tea maker
Spring Street Cabin #2
9.0 out of 10, Wonderful, (2)
"Plenty of privacy and everything you need. The owner was great at communicating."
The price is NZ$348
includes taxes & fees
2 Jun - 3 Jun
Spring Street Cabin #2
Exterior
Hillside Cabin #1 Annapolis, MO Black River
9.6 out of 10, Exceptional, (35)
"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 NZ$400
includes taxes & fees
20 Jun - 21 Jun
Hillside Cabin #1 Annapolis, MO Black River
Smart TV
Small Town Lodge - Black River
4.0 out of 10, (1)
The price is NZ$508
includes taxes & fees
28 May - 29 May
Small Town Lodge - Black River
Dining
FS Cabin #4 - Close to Black River
8.0 out of 10, Very good, (1)
"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 NZ$325
includes taxes & fees
27 Jun - 28 Jun
FS Cabin #4 - Close to Black River
Property grounds
A Place To Relax-Side A
10.0 out of 10, Exceptional, (17)
"I enjoyed a comfortable and peaceful overnight visit! I love walking around the property and trails."
The price is NZ$291
includes taxes & fees
9 Jun - 10 Jun
A Place To Relax-Side A
Property grounds
Micro house cabin located near Silver Mines Recreation Area.
10.0 out of 10, Exceptional, (40)
"This was my second stay at this great micro cabin. Very close to outdoor activities and a perfect home base. Viewed the total eclipse at the Castor River Shut-ins. The eclipse was spectacular and it was nice to return to the cabin afterward rather than fight traffic. This cabin is small as advertised but has absolutely everything you need to enjoy time outdoors in a beautiful area."
Micro house cabin located near Silver Mines Recreation Area.
Outdoor dining
Newly remodeled offers many amenities with perfect location!
10.0 out of 10, Exceptional, (12)
"Property has everything you need, and more. Comfy, clean, quiet, efficient, and relaxing. Great staging area for SE Missouri fun. Will look to stay here again in the future."
Newly remodeled offers many amenities with perfect location!
Pool
River front property HOT TUB, Kayak, tubing, and fishing
9.6 out of 10, Exceptional, (70)
"A little difficult to find. Other wise great. "
The price is NZ$448
includes taxes & fees
28 May - 29 May
River front property HOT TUB, Kayak, tubing, and fishing
Outdoor pool
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
10.0 out of 10, Exceptional, (51)
"We came with our whole family for a family vacation. We definitely enjoyed our time there even with three toddlers. The property is well cleaned and taken care of. My toddler’s favorite things to do during our stay was saying hi to the pony every morning, swimming, and playing with the neighbor dogs outside."
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Fridge, microwave, oven, stovetop
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
10.0 out of 10, Exceptional, (4)
"perfect location and very private place."
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
Don't see what you're looking for?
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.

Other types of properties in Annapolis you may be interested in

Fridge, microwave, oven, stovetop
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, (24)
"Really a nice and clean and cozy stay."
The price is NZ$351
includes taxes & fees
28 May - 29 May
Hillside Cabin #3 Annapolis, MO Black River
Exterior
Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (58)
"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
Exterior
Hillside Cabin #4 Annapolis, MO Black River
9.6 out of 10, Exceptional, (29)
"Nice new cabin, looks exactly like the pictures. We enjoyed our stay and the host was awesome!"
The price is NZ$448
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Annapolis holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Annapolis. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Annapolis. Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Annapolis short-term rentals, that won’t be hard to do.

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.

Recent reviews of Annapolis properties
Expedia verified reviews