Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Make your reservation fast as inquiries are coming in daily.

9.8 out of 10, Exceptional, (53)
"Great time and a wonderful property"
Make your reservation fast as inquiries are coming in daily.

Hillside Cabin #4 Annapolis, MO Black River

9.6 out of 10, Exceptional, (36)
"This was perfect for a friends float trip! "
The price is HK$1,484
HK$2,504 total
includes taxes & fees
15 Jul - 16 Jul
Hillside Cabin #4 Annapolis, MO Black River

Rustic River Cabin Getaway

9.8 out of 10, Exceptional, (73)
"Perfect weekend getaway close to the Black River."
Rustic River Cabin Getaway

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

9.0 out of 10, Wonderful, (9)
"We enjoyed the cabin at nights after floating the black river. "
Relaxing 3B Log Home-15 min walk to the Black River!

Completely Renovated in May 2023

8.4 out of 10, Very good, (7)
"Love the people, town,float trip, and lil cabin#3 was perfect for family and pets"
The price is HK$975
HK$1,776 total
includes taxes & fees
24 Jul - 25 Jul
Completely Renovated in May 2023

FS Rental #1 - 5mins to Black River

6.8 out of 10, (3)
"Nice little place with good sleeping and room to stretch out."
The price is HK$1,144
HK$2,071 total
includes taxes & fees
23 Jul - 24 Jul
FS Rental #1 - 5mins to Black River

New Cabin Just Minutes from Black River

8.0 out of 10, Very good, (4)
"Owner communicated well and the place was a nice clean place for us to stay "
The price is HK$1,356
HK$2,361 total
includes taxes & fees
24 Jul - 25 Jul
New Cabin Just Minutes from Black River

Just Minutes from Black River – With WIFI

6.8 out of 10, (5)
"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...
The price is HK$933
HK$1,702 total
includes taxes & fees
14 Jul - 15 Jul
Just Minutes from Black River – With WIFI

Hillside Cabin #3 Annapolis, MO Black River

7.8 out of 10, Good, (26)
"Really a nice and clean and cozy stay."
The price is HK$933
HK$1,702 total
includes taxes & fees
13 Jul - 14 Jul
Hillside Cabin #3 Annapolis, MO Black River

Secluded Log Cabin

9.8 out of 10, Exceptional, (22)
"Beds were comfortable, outdoor area was wonderful, not far from town. Enjoyed our stay very much."
Secluded Log Cabin

Hillside Cabin #2 Annapolis, MO Black River

9.4 out of 10, Exceptional, (58)
"Me and my spent the weekend in cabin 2. Overall good experience as no one else was there. Not quite as secluded as I would prefer. Cabins are too close together and at the edge of town "
The price is HK$1,017
HK$1,802 total
includes taxes & fees
23 Jul - 24 Jul
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River

9.4 out of 10, Exceptional, (36)
"The cabin was exactly like the pictures showed. It worked out perfectly for our family with just enough room to spread out, and with a large main area that we could hang out together comfortably. We took advantage of the spacious patio and enjoyed a fire each night. I would definitely stay again."
The price is HK$1,272
HK$2,269 total
includes taxes & fees
13 Jul - 14 Jul
Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #5 Annapolis, MO

9.2 out of 10, Wonderful, (5)
"Booked a last minute canoe trip on the Black River andn this property was ideally located and included everything necessary for an early breakfast before hitting the river."
The price is HK$1,017
HK$1,802 total
includes taxes & fees
13 Jul - 14 Jul
Hillside Cabin #5 Annapolis, MO

Completely Renovated in May 2023

9.6 out of 10, Exceptional, (4)
"Cute little place, not far from the river"
The price is HK$975
HK$1,791 total
includes taxes & fees
13 Jul - 14 Jul
Completely Renovated in May 2023

RIVER and SKY Cabin; Hot Tub

The price is HK$998
HK$1,615 total
includes taxes & fees
23 Jul - 24 Jul
RIVER and SKY Cabin; Hot Tub

Sam A Baker State Park

2.0 star property
The price is HK$981
HK$1,040 total
includes taxes & fees
5 Aug - 6 Aug
Sam A Baker State Park

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

10.0 out of 10, Exceptional, (26)
"Beautiful property, I’d recommend to anyone going here to stay here."
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Five minute walk to middle fork Black River, 7 miles to Johnson Shut ins.

10.0 out of 10, Exceptional, (19)
"Everything was absolutely amazing and Miss Wendy was such an amazing woman and the sweetest ever definitely would stay again!"
Five minute walk to middle fork Black River, 7 miles to Johnson Shut ins.

Johnson's Shut-ins State Park

3.0 star property
Johnson's Shut-ins State Park

Lake Road Cabin C — Million Dollar Ozark View!

10.0 out of 10, Exceptional, (17)
"The cabin was so cute and perfect for the weekend. "
The price is HK$699
HK$1,244 total
includes taxes & fees
24 Jul - 25 Jul
Lake Road Cabin C — Million Dollar Ozark View!
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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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. Some other top choices in Annapolis are Just Minutes from Black River – With WIFI and Secluded Log Cabin.

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?

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