Default HTG hotel image

Annapolis Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 holiday rentals

A cabin interior with a loft bed, a chair, and a ceiling fan.

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 HK$949
HK$1,702 total
includes taxes & fees
24 Sept - 25 Sept
Hillside Cabin #2 Annapolis, MO Black River
A compact kitchen with wooden cabinets, a large TV, and various kitchen utensils hanging on the wall.

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 HK$854
HK$1,631 total
includes taxes & fees
24 Sept - 25 Sept
FS Rental #4 Annapolis, MO Black River
A kitchen with wooden cabinets, a central island with stools, a microwave, a refrigerator, and a stove.

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 HK$1,035
HK$1,977 total
includes taxes & fees
24 Sept - 25 Sept
Hillside Cabin #1 Annapolis, MO Black River
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
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 HK$1,035
HK$1,969 total
includes taxes & fees
27 Sept - 28 Sept
Small Town Lodge - 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.

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 HK$949
HK$1,702 total
includes taxes & fees
24 Sept - 25 Sept
Hillside Cabin #5 Annapolis, MO

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 HK$949
HK$1,828 total
includes taxes & fees
29 Sept - 30 Sept
FS Rental #1 Annapolis, MO Black River
A wooden deck with chairs and a fire pit in a forested area.

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 HK$820
HK$1,557 total
includes taxes & fees
24 Sept - 25 Sept
Hillside Cabin #3 Annapolis, MO Black River
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
8.2 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 HK$820
HK$1,588 total
includes taxes & fees
24 Sept - 25 Sept
FS Rental #3 Annapolis, MO Black River
A modern room with a large window, two chairs, a small wooden table, and a view of a forest.

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 HK$1,247
HK$1,961 total
includes taxes & fees
29 Sept - 30 Sept
RIVER and SKY Cabin; Hot Tub
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, (45 reviews)
"Would stay here again"
United States
Steve A.
The price is HK$941
HK$1,152 total
includes taxes & fees
24 Sept - 25 Sept
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
A rustic wooden cabin with a porch, a bench, and a door.

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 HK$1,255
HK$1,492 total
includes taxes & fees
24 Sept - 25 Sept
Ride Trails or go fishing near Clearwater lake. No cleaning fees, pet friendly
A rustic log cabin with a stone foundation, surrounded by trees and a wooden fence.

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 HK$1,059
HK$1,122 total
includes taxes & fees
11 Oct - 12 Oct
Sam A Baker State Park
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, (31 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
The price is HK$847
HK$1,409 total
includes taxes & fees
30 Sept - 1 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
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$690
HK$1,699 total
includes taxes & fees
29 Sept - 30 Sept
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
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 HK$588
HK$947 total
includes taxes & fees
5 Oct - 6 Oct
Cozy hobby farm cabin under the stars!
A bedroom with a bed, a bench, and a ceiling fan.

16. AV Bungalows #9B

AV Bungalows #9B
Arcadia
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$1,062
HK$1,309 total
includes taxes & fees
24 Sept - 25 Sept
AV Bungalows #9B
A porch with four green Adirondack chairs, a small table, and string lights.

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 HK$1,027
HK$2,109 total
includes taxes & fees
28 Sept - 29 Sept
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

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 traveller
The price is HK$1,122
HK$1,613 total
includes taxes & fees
24 Sept - 25 Sept
Mountain View at Pickle & Perk
A dining area with a table and chairs, wooden cabinets, and a kitchen with an archway.

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 HK$2,353
HK$3,948 total
includes taxes & fees
24 Sept - 25 Sept
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
A modern kitchen with dark cabinets, a built-in microwave, a flat-screen TV, and a large window with a view of the street.

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is HK$941
HK$1,709 total
includes taxes & fees
29 Sept - 30 Sept
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 3 days ago
Fort Davidson Hotel

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?

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 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.