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Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Annapolis holiday rentals

A compact kitchen with wooden cabinets, a large TV, and various kitchen utensils hanging on the wall.

1. FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (10 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is HK$853
HK$1,629 total
includes taxes & fees
25 Oct - 26 Oct
FS Rental #4 Annapolis, MO Black River
A cabin interior with a loft bed, a chair, and a ceiling fan.

2. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (66 reviews)
"The cabin was very nice but looks a little un loved. 6 nights no tv in the evening and no reply. Looks like no one is doing up keep on the place. We did love how close we were to the river and the store. Very quite and private property. Shower curtain had a lot of mildew build up. Would give it 4 stars if it was cleaner and everything worked."
United States
Tim S.
The price is HK$948
HK$1,701 total
includes taxes & fees
25 Oct - 26 Oct
Hillside Cabin #2 Annapolis, MO Black River
A kitchen with dark cabinets, a stainless steel refrigerator, a built-in oven, a microwave, and a flat-screen TV mounted above the counter.

3. Hillside Cabin #5 Annapolis, MO

Hillside Cabin #5 Annapolis, MO
Annapolis
9.2 out of 10, Wonderful, (5 reviews)
"Great location and very clean."
United States
Mary C.
The price is HK$948
HK$1,701 total
includes taxes & fees
25 Oct - 26 Oct
Hillside Cabin #5 Annapolis, MO
A cozy living room with a brown leather sofa, a small table with a lamp, and a wooden floor. A kitchen with wooden cabinets and a dining area with a table and chairs are visible in the background.

4. Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
8.4 out of 10, Very good, (9 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
The price is HK$1,034
HK$1,967 total
includes taxes & fees
26 Oct - 27 Oct
Small Town Lodge - Annapolis, MO Black River
A kitchen with wooden cabinets, a central island with stools, a microwave, a refrigerator, and a stove.

5. Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (41 reviews)
"Very grateful for this safe clean cabin. We were there during the terrible Black River flooding and thankfully this cabin was in safe high ground. "
United States
Leslie
The price is HK$1,034
HK$1,975 total
includes taxes & fees
25 Oct - 26 Oct
Hillside Cabin #1 Annapolis, MO Black River
Living Room & Dining Area

6. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
8.0 out of 10, Very good, (7 reviews)
"We enjoyed our stay here. It was a great place for the 8 of us to stay. We were going over to Sam A Baker to join family camping there. We would stay here again if available. "
United States
Sue F.
The price is HK$948
HK$1,826 total
includes taxes & fees
25 Oct - 26 Oct
FS Rental #1 Annapolis, MO Black River
A modern room with a large window, two chairs, a small wooden table, and a view of a forest.

7. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.2 out of 10, Wonderful, (7 reviews)
"Lpleasant environment, beautiful view, the cabin was super clean and enjoyableonly note being the bed was stiff and pillows were thin but overall would recommend"
United States
Teresa C.
The price is HK$1,246
HK$1,960 total
includes taxes & fees
29 Oct - 30 Oct
RIVER and SKY Cabin; Hot Tub
A modern kitchen with a large TV, stainless steel appliances, and a wooden floor.

8. FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.4 out of 10, Very good, (14 reviews)
"Ac needs an update, or add window units. Beautiful stay and beautiful location. About 7 minutes from the river. Train runs in front at 1am and 4am just a heads up. "
United States
Jessica W.
The price is HK$819
HK$1,603 total
includes taxes & fees
27 Oct - 28 Oct
FS Rental #3 Annapolis, MO Black River
A wooden deck with chairs and a fire pit in a forested area.

9. Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River
Annapolis
7.8 out of 10, Good, (30 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
The price is HK$819
HK$1,556 total
includes taxes & fees
15 Nov - 16 Nov
Hillside Cabin #3 Annapolis, MO Black River
A kitchen with wooden cabinets, a microwave, a coffee maker, a stove, and a sink.

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

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Piedmont
10.0 out of 10, Exceptional, (48 reviews)
"Would stay here again"
United States
Steve A.
The price is HK$940
HK$1,151 total
includes taxes & fees
26 Oct - 27 Oct
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
A view through a window with a stone wall and a wooden structure in the background.

11. Sam A Baker State Park

Sam A Baker State Park
2.0 star property
Patterson
9.0 out of 10, Wonderful, (6 reviews)
"Pet friendly, great staff. "
United States
Charlie
The price is HK$1,058
HK$1,121 total
includes taxes & fees
1 Nov - 2 Nov
Sam A Baker State Park
A campsite with a tent, a blue canopy, and a river.

12. Ride Trails or go fishing near Clearwater lake. No cleaning fees, pet friendly

Ride Trails or go fishing near Clearwater lake. No cleaning fees, pet friendly
Piedmont
10.0 out of 10, Exceptional, (2 reviews)
"Clean rooms. Great quality of craftsmanship in the cabin. Cold ac full fridge. Everything looked exactly like the pics ..you get what you pay for and more. Will definitely go back again. And recommend"
United States
Mike A.
The price is HK$1,254
HK$1,490 total
includes taxes & fees
4 Nov - 5 Nov
Ride Trails or go fishing near Clearwater lake. No cleaning fees, pet friendly
A kitchen with wooden cabinets, a toaster, and a dishwasher.

13. Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (32 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
The price is HK$846
HK$1,400 total
includes taxes & fees
26 Oct - 27 Oct
Lake Road Cabin C — Million Dollar Ozark View!
A modern kitchen with dark cabinets, a built-in microwave, a flat-screen TV, and a large window with a view of the street.

14. Ironton Hub: Near Elephant Rocks & Shut-ins

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is HK$784
HK$1,537 total
includes taxes & fees
25 Oct - 26 Oct
Ironton Hub: Near Elephant Rocks & Shut-ins
A cozy cabin-style room with a wooden interior, a sofa, a dining table, and a kitchen area.

15. Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Patterson
9.6 out of 10, Exceptional, (12 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is HK$588
HK$946 total
includes taxes & fees
1 Nov - 2 Nov
Cozy hobby farm cabin under the stars!
A modern kitchen with dark cabinets, a built-in microwave, a flat-screen TV, and a large window with a view of the street.

16. Ironton Hub: Near Elephant Rocks & Shut-Ins

Ironton Hub: Near Elephant Rocks & Shut-Ins
Ironton
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Perfect for the short stay we needed. Clean and convenient. Will recommend."
United States
angie m.
The price is HK$556
HK$1,552 total
includes taxes & fees
25 Oct - 26 Oct
Ironton Hub: Near Elephant Rocks & Shut-Ins
A bedroom with a bed, a bench, and a ceiling fan.

17. AV Bungalows #9B

AV Bungalows #9B
Arcadia
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I really enjoyed our stay! The Bungalow was perfect for us and will definitely be staying again when we come back to Arcadia!!"
United States
Theresa R.
The price is HK$1,061
HK$1,308 total
includes taxes & fees
25 Oct - 26 Oct
AV Bungalows #9B
A dining area with a table and chairs, wooden cabinets, and a kitchen with an archway.

18. Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Lesterville
9.0 out of 10, Wonderful, (20 reviews)
"Ellen is a Very communicative and helpful host. Property looks even better in person than in the pictures. Enjoyable stay!"
United States
Robert H.
The price is HK$2,351
HK$3,945 total
includes taxes & fees
3 Nov - 4 Nov
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

19. Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (31 reviews)
"Perfect getaway, great experience. Hosts are phenomenal, food and coffee drinks are excellent. Highly recommend."
United States
Anonymous traveller
The price is HK$1,121
HK$1,596 total
includes taxes & fees
28 Oct - 29 Oct
Mountain View at Pickle & Perk
A hot tub in a covered outdoor area with a view of a swimming pool and a wooden play structure in the background.

20. Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
Fredericktown
10.0 out of 10, Exceptional, (15 reviews)
"This was one of the best stays we have ever had! The owners Cathy and Richard are absolutely incredible! They go above and beyond to make sure you have the best time possible! The amities are just non stop! I 100% recommend and will definitely be back!"
United States
Lexis
The price is HK$1,371
HK$1,660 total
includes taxes & fees
25 Oct - 26 Oct
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
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

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

10/10 Excellent
"Very nice suclueded area. Beautiful, clean, affordable and right next to K park Black River. Love the layout of this cabin they all are great but for us two we loved the size and area. Highly recommend to anyone looking to get away in a peaceful environment!"
Mary K. 1-night trip
Posted 2 weeks ago
Hillside Cabin #2 Annapolis, MO Black River

Find out more about Annapolis

Search for holiday rentals in Annapolis on Expedia! You can easily find your home rentals, villas, holiday apartments in Annapolis using one of the methods below:

  • View our selection of featured holiday rentals in Annapolis
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annapolis while they last

Look no further and take a look at our great range of rental properties in Annapolis!

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?

Secluded Log Cabin: This highly rated holiday home rental in Annapolis is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.