Annapolis Holiday Rentals: Short-Term Accommodations for Rent

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Annapolis

Corey M.

HK$1,559 total

includes taxes & fees

10 Nov - 11 Nov

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

2. Hillside Cabin #2 Annapolis, MO Black River

Annapolis

Hans S.

HK$1,560 total

includes taxes & fees

9 Nov - 10 Nov

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

Annapolis

Mary C.

HK$1,560 total

includes taxes & fees

9 Nov - 10 Nov

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

Annapolis

Jeremy H.

HK$1,803 total

includes taxes & fees

9 Nov - 10 Nov

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

Annapolis

Rik B.

HK$1,811 total

includes taxes & fees

9 Nov - 10 Nov

6. FS Rental #1 Annapolis, MO Black River

Annapolis

Jasonl C.

HK$1,740 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a large TV, stainless steel appliances, and a wooden floor.

7. FS Rental #3 Annapolis, MO Black River

Annapolis

Jessica W.

HK$1,517 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with chairs and a fire pit in a forested area.

8. Hillside Cabin #3 Annapolis, MO Black River

Annapolis

Adam G.

HK$1,486 total

includes taxes & fees

15 Nov - 16 Nov

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

Fredericktown

Teresa C.

HK$1,874 total

includes taxes & fees

6 Dec - 7 Dec

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

Piedmont

Steve A.

HK$1,089 total

includes taxes & fees

9 Nov - 10 Nov

A wooden deck structure with a red exterior and string lights, a car parked nearby, and a tree in the foreground.

11. Cozy hobby farm cabin under the stars with treehouse, & hot tub

Patterson

Wyatt S.

HK$917 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a fireplace, leather sofa, and a flat-screen TV mounted above it.

12. Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool

Arcadia

Julie H.

HK$1,530 total

includes taxes & fees

9 Nov - 10 Nov

A rustic log cabin with a stone foundation, surrounded by trees and a wooden fence.

13. Sam A Baker State Park

Patterson

Charlie

HK$1,122 total

includes taxes & fees

9 Nov - 10 Nov

A rustic wooden cabin with a porch, a swing, and a welcome sign.

14. Escape to Clearwater Lake and Upper Black River, Pet Friendly

Piedmont

Mike A.

HK$1,436 total

includes taxes & fees

10 Nov - 11 Nov

A kitchen with wooden cabinets, a toaster, and a dishwasher.

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

Ironton

Heather the Librarian

HK$1,338 total

includes taxes & fees

10 Nov - 11 Nov

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

angie m.

HK$1,514 total

includes taxes & fees

9 Nov - 10 Nov

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

Ironton

HK$1,554 total

includes taxes & fees

9 Nov - 10 Nov

A serene lakeside setting with a wooden dock and a gazebo.

18. Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.

Ironton

shirley w.

HK$2,432 total

includes taxes & fees

29 Nov - 30 Nov

A compact living space with a sofa, a flat-screen TV mounted on the wall, a red refrigerator, and wooden beams on the ceiling.

19. The Mustard Seed - Cozy Tiny Home in the Ozarks

Patterson

HK$933 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a table and chairs, wooden cabinets, and a kitchen with an archway.

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

Lesterville

Robert H.

HK$3,781 total

includes taxes & fees

9 Nov - 10 Nov

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Top Annapolis Hotel Reviews

Madison Inn Lodge

10/10 Excellent

"Room was very clean . The bathroom wall had been repaired and it was done sloppy . Roughly patched and paint on floor . Staff was super friendly"

Lake Road Cabin B — Million Dollar Ozark View!

10/10 Excellent

"We stayed four nights October 2026 in the cabin and enjoyed every minute of it. It was extremely clean, comfortable, great beds, nice shower, close to the state parks, restaurants and other historic treasures. Katie was a great hostess and the check-in in and out process easy! We will be coming back and staying here again.Robin and Monte"

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!"

RIVER and SKY Cabin; Hot Tub

8/10 Good

"Please read - the property is just how the pictures show with one exception the bathroom is up a relatively steep gravel hill in a separate building. When booking this property, the description did not say anything about having to go to a separate building approximately 100 feet away from the main house so in the middle of the night when you have to go pee, having to get dressed and go up a steep hill in the woods was unexpected.That said we very much enjoyed the property. It was very secluded with a beautiful view. We were only there one night so having to go up and down the hill to use the bathroom was not a dealbreaker for us, but I don’t think I would want to stay longer with not having a bathroom nearby - especially for the price that was paid I would expect to have a bathroom more accessible in the property. The path to get from where you park and where the bathhouse is down to the property is gravel and pretty steep so it’s not for somebody That’s not sure footed."

Find out more about Annapolis

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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.

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Check prices for these dates

Our top choices for Annapolis holiday rentals

1. FS Rental #4 Annapolis, MO Black River

2. Hillside Cabin #2 Annapolis, MO Black River

3. Hillside Cabin #5 Annapolis, MO

4. Small Town Lodge - Annapolis, MO Black River

5. Hillside Cabin #1 Annapolis, MO Black River

6. FS Rental #1 Annapolis, MO Black River

7. FS Rental #3 Annapolis, MO Black River

8. Hillside Cabin #3 Annapolis, MO Black River

9. RIVER and SKY Cabin; Hot Tub

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

11. Cozy hobby farm cabin under the stars with treehouse, & hot tub

12. Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool

13. Sam A Baker State Park

14. Escape to Clearwater Lake and Upper Black River, Pet Friendly

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

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

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

18. Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.

19. The Mustard Seed - Cozy Tiny Home in the Ozarks

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

Find holiday rentals that suit your style

Top Annapolis Hotel Reviews

Madison Inn Lodge

Shepherd Mountain Inn

Lake Road Cabin B — Million Dollar Ozark View!

St Francis River: The Blue Yurt and Hot Tub

Small Town Lodge - Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

RIVER and SKY Cabin; Hot Tub

FS Rental #4 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River

Find out more about Annapolis

Frequently asked questions

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