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Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

1. 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 NZ$348
includes taxes & fees
12 Sept - 13 Sept
FS Rental #4 Annapolis, MO Black River

2. 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 NZ$362
includes taxes & fees
12 Sept - 13 Sept
Hillside Cabin #2 Annapolis, MO Black River

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 NZ$362
includes taxes & fees
14 Sept - 15 Sept
Hillside Cabin #5 Annapolis, MO

4. Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (40 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 NZ$422
includes taxes & fees
12 Sept - 13 Sept
Hillside Cabin #1 Annapolis, MO Black River

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 NZ$420
includes taxes & fees
12 Sept - 13 Sept
Small Town Lodge - Annapolis, MO Black River

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 NZ$389
includes taxes & fees
12 Sept - 13 Sept
FS Rental #1 Annapolis, MO Black River

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 NZ$340
includes taxes & fees
12 Sept - 13 Sept
FS Rental #3 Annapolis, MO Black River

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 NZ$334
includes taxes & fees
12 Sept - 13 Sept
Hillside Cabin #3 Annapolis, MO Black River

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 traveller
The price is NZ$423
includes taxes & fees
16 Aug - 17 Aug
RIVER and SKY Cabin; Hot Tub

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 traveller
The price is NZ$251
includes taxes & fees
16 Aug - 17 Aug
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

11. 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 NZ$305
includes taxes & fees
16 Aug - 17 Aug
Lake Road Cabin C — Million Dollar Ozark View!

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 NZ$244
includes taxes & fees
25 Aug - 26 Aug
Sam A Baker State Park

13. 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 NZ$370
includes taxes & fees
18 Aug - 19 Aug
Ironton Hub: Near Elephant Rocks & Shut-Ins

14. Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Greenville
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is NZ$204
includes taxes & fees
9 Sept - 10 Sept
Cozy hobby farm cabin under the stars!

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is NZ$372
includes taxes & fees
18 Aug - 19 Aug
Ironton Hub: Near Elephant Rocks & Shut-ins

16. Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (28 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 NZ$347
includes taxes & fees
22 Aug - 23 Aug
Mountain View at Pickle & Perk

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 NZ$285
includes taxes & fees
18 Aug - 19 Aug
AV Bungalows #9B

18. *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 NZ$477
includes taxes & fees
19 Aug - 20 Aug
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

19. Pickleball Cafe & Micro Hotel

Pickleball Cafe & Micro Hotel
Ironton
10.0 out of 10, Exceptional, (28 reviews)
"Great place to get away. Loved the coffee . "
United States
Craig C.
The price is NZ$395
includes taxes & fees
16 Aug - 17 Aug
Pickleball Cafe & Micro Hotel

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 NZ$356
includes taxes & fees
15 Aug - 16 Aug
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

Find out more about Annapolis

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.

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.