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Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Annapolis vacation rentals

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

1. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (63 reviews)
"great place to get away. plan to cook/grill there, or drive 30 minutes for food. however, this solitude and quiet is exactly why we booked here. and gorgeous roads, hikes, sites in every direction."
United States
Hans S.
The price is AED 444
AED 797 total
includes taxes & fees
25 Sep - 26 Sep
Hillside Cabin #2 Annapolis, MO Black River
Coffee/tea maker, fridge, microwave, oven

2. FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (9 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is AED 400
AED 764 total
includes taxes & fees
25 Sep - 26 Sep
FS Rental #4 Annapolis, MO Black River
Coffee/tea maker, fridge, microwave, oven

3. 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 AED 485
AED 926 total
includes taxes & fees
27 Sep - 28 Sep
Hillside Cabin #1 Annapolis, MO Black River
Smart TV

4. Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
9.0 out of 10, Wonderful, (8 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
The price is AED 485
AED 922 total
includes taxes & fees
27 Sep - 28 Sep
Small Town Lodge - Annapolis, MO Black River
Coffee/tea maker, fridge, microwave, oven

5. 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 AED 444
AED 797 total
includes taxes & fees
27 Sep - 28 Sep
Hillside Cabin #5 Annapolis, MO
Smart TV

6. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
8.0 out of 10, Very good, (6 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 AED 444
AED 856 total
includes taxes & fees
25 Sep - 26 Sep
FS Rental #1 Annapolis, MO Black River
Terrace/patio

7. Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River
Annapolis
7.8 out of 10, Good, (29 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
The price is AED 384
AED 729 total
includes taxes & fees
25 Sep - 26 Sep
Hillside Cabin #3 Annapolis, MO Black River
Coffee/tea maker, fridge, microwave, oven

8. FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.2 out of 10, Very good, (13 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 AED 384
AED 744 total
includes taxes & fees
27 Sep - 28 Sep
FS Rental #3 Annapolis, MO Black River
Interior

9. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.4 out of 10, Exceptional, (6 reviews)
"Great getaway"
United States
Anonymous traveler
The price is AED 584
AED 918 total
includes taxes & fees
29 Sep - 30 Sep
RIVER and SKY Cabin; Hot Tub
Coffee/tea maker, fridge, microwave, oven

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, (46 reviews)
"Would stay here again"
United States
Steve A.
The price is AED 441
AED 506 total
includes taxes & fees
25 Sep - 26 Sep
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Terrace/patio

11. 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, (1 review)
"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 AED 588
AED 698 total
includes taxes & fees
27 Sep - 28 Sep
Ride Trails or go fishing near Clearwater lake. No cleaning fees, pet friendly
Family Cabin

12. 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 AED 496
AED 525 total
includes taxes & fees
11 Oct - 12 Oct
Sam A Baker State Park
Interior

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 AED 397
AED 656 total
includes taxes & fees
29 Sep - 30 Sep
Lake Road Cabin C — Million Dollar Ozark View!
Interior

14. 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 AED 323
AED 796 total
includes taxes & fees
3 Oct - 4 Oct
Ironton Hub: Near Elephant Rocks & Shut-Ins
Interior

15. Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Patterson
10.0 out of 10, Exceptional, (11 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is AED 275
AED 443 total
includes taxes & fees
5 Oct - 6 Oct
Cozy hobby farm cabin under the stars!
1 bedroom, iron/ironing board, WiFi, bed sheets

16. 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 AED 498
AED 613 total
includes taxes & fees
27 Sep - 28 Sep
AV Bungalows #9B
Terrace/patio

17. *State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (41 reviews)
"Great place to stay!"
United States
Derek R.
The price is AED 481
AED 988 total
includes taxes & fees
28 Sep - 29 Sep
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
1 bedroom, in-room safe, desk, iron/ironing board

18. Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (29 reviews)
"Perfect getaway, great experience. Hosts are phenomenal, food and coffee drinks are excellent. Highly recommend."
United States
Anonymous traveler
The price is AED 526
AED 755 total
includes taxes & fees
25 Sep - 26 Sep
Mountain View at Pickle & Perk
Dining

19. 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)
"Great house and location."
United States
Thomas M.
The price is AED 1,102
AED 1,849 total
includes taxes & fees
25 Sep - 26 Sep
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Apartment (1 Bedroom) | Interior

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is AED 441
AED 800 total
includes taxes & fees
29 Sep - 30 Sep
Ironton Hub: Near Elephant Rocks & Shut-ins
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

Fort Davidson Hotel

Fort Davidson Hotel

10/10 Excellent
"Checkin was wonderful! Made a personal connection with the host. The room was very clean and easy to navigate to the Arcadia Academy wedding venue for the entire weekend of festivities. The pool area was well maintained used by family kiddos during our stay. Loved the nostalgia of the location, with history and so much to do in the valley. Thank you!!"
Lisa 2-night trip
Posted 4 days ago
Fort Davidson Hotel

Frequently asked questions

Can I find a vacation rental in Annapolis?

Yes, we give you a choice of vacation rentals close to top local attractions in Annapolis, or you can select a more secluded option if you want a relaxing place to 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 vacation rentals in Annapolis?

Secluded Log Cabin: Visitors give good reviews to this Annapolis vacation home rental, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Annapolis?

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

What can I see and do in Annapolis?

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

What are vacation rentals like in Annapolis?

Vacation rentals are private accommodations you can stay in for a short or long stay in Annapolis. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.