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Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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
9.2 out of 10, Wonderful, (61 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 ￥20,777
￥36,045 total
includes taxes & fees
Aug 2 - Aug 3
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
9.6 out of 10, Exceptional, (7 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is ￥19,911
￥35,808 total
includes taxes & fees
Aug 2 - Aug 3
FS Rental #4 Annapolis, MO Black River
Coffee/tea maker, fridge, microwave, oven

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 ￥20,777
￥36,360 total
includes taxes & fees
Aug 4 - Aug 5
Hillside Cabin #5 Annapolis, MO
Coffee/tea maker, fridge, microwave, oven

4. Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (39 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 ￥25,971
￥46,118 total
includes taxes & fees
Aug 2 - Aug 3
Hillside Cabin #1 Annapolis, MO Black River
Smart TV

5. 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 ￥27,702
￥47,849 total
includes taxes & fees
Aug 2 - Aug 3
Small Town Lodge - Annapolis, MO Black River
Smart TV

6. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
7.6 out of 10, Good, (5 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 ￥23,374
￥41,790 total
includes taxes & fees
Aug 3 - Aug 4
FS Rental #1 Annapolis, MO Black River
Coffee/tea maker, fridge, microwave, oven

7. 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 ￥19,911
￥36,123 total
includes taxes & fees
Aug 3 - Aug 4
FS Rental #3 Annapolis, MO Black River
Terrace/patio

8. Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River
Annapolis
7.8 out of 10, Good, (27 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
The price is ￥19,045
￥34,155 total
includes taxes & fees
Aug 2 - Aug 3
Hillside Cabin #3 Annapolis, MO Black River
Interior

9. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.2 out of 10, Wonderful, (5 reviews)
"Great getaway"
United States
Anonymous traveler
The price is ￥25,027
￥39,675 total
includes taxes & fees
Aug 4 - Aug 5
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, (43 reviews)
"Perfect cabin for a fishing trip. My Dad and I loved staying there."
United States
Anonymous traveler
The price is ￥18,888
￥23,117 total
includes taxes & fees
Aug 2 - Aug 3
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Family Cabin

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 ￥21,249
￥22,519 total
includes taxes & fees
Aug 18 - Aug 19
Sam A Baker State Park
Interior

12. Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Greenville
10.0 out of 10, Exceptional, (6 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is ￥12,592
￥19,829 total
includes taxes & fees
Aug 3 - Aug 4
Cozy hobby farm cabin under the stars!
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, (30 reviews)
"This is a very cozy, comfortable and quiet space. This cabin has everything you need and is close to restaurants and Elephant Rocks State Park. I would recommend to anyone visiting the area! Thank you!"
United States
Michelle
The price is ￥16,999
￥28,283 total
includes taxes & fees
Aug 9 - Aug 10
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, (1 review)
"Great stay. Perfect for the short stay we needed. Clean and convenient. Will recommend."
United States
angie m.
The price is ￥13,851
￥34,094 total
includes taxes & fees
Aug 4 - Aug 5
Ironton Hub: Near Elephant Rocks & Shut-Ins
Interior

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is ￥18,888
￥34,302 total
includes taxes & fees
Aug 4 - Aug 5
Ironton Hub: Near Elephant Rocks & Shut-ins
Dining

16. 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, (19 reviews)
"Great house and location."
United States
Thomas M.
The price is ￥47,220
￥79,226 total
includes taxes & fees
Aug 3 - Aug 4
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Terrace/patio

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

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay!"
United States
Derek R.
The price is ￥21,839
￥43,836 total
includes taxes & fees
Aug 19 - Aug 20
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
1 bedroom, iron/ironing board, WiFi, bed sheets

18. 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 ￥21,320
￥26,275 total
includes taxes & fees
Aug 2 - Aug 3
AV Bungalows #9B
1 bedroom, in-room safe, desk, iron/ironing board

19. Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (26 reviews)
"Our stay was excellent. The rooms were cozy and a perfect location to get to Elephant Rock and Johnson Shut-Ins."
United States
Cara J.
The price is ￥22,524
￥32,362 total
includes taxes & fees
Aug 3 - Aug 4
Mountain View at Pickle & Perk
Outdoor pool

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
9.8 out of 10, Exceptional, (8 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 ￥27,545
￥33,175 total
includes taxes & fees
Aug 2 - Aug 3
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

Shepherd Mountain Inn

Shepherd Mountain Inn

10/10 Excellent
"We love the motel vibe and that's exactly what we got! The owner of the property and the restaurant was at the front desk when we arrived, and he was super friendly and helpful. He even gave us some samples of their beef sticks, which were phenomenal, and we highly recommend you ask about! The room was super clean with plenty of towels and an ice-cold refrigerator. We ate dinner at the restaurant in front of the property, and it was excellent also! The pulled pork and ribeye are delicious! The next morning we ate the free breakfast in the lobby, and it was, again, excellent! Close by lots of sites to visit, a very convenient location. Overall, we were very impressed, and if we are ever back that way, we will stay there again. Highly recommend!"
Walter 2-night trip
Posted 4 days ago
Shepherd Mountain Inn

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 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?

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 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.