Holiday Rentals in Annapolis

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Check prices for these dates

Our top choices for Annapolis holiday rentals

1. FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.2 out of 10, Wonderful, (11 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
The price is €177
includes taxes & fees
11 Nov - 12 Nov
FS Rental #4 Annapolis, MO Black River

2. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (66 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 €189
includes taxes & fees
11 Nov - 12 Nov
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 €184
includes taxes & fees
11 Nov - 12 Nov
Hillside Cabin #5 Annapolis, MO

4. Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
8.4 out of 10, Very good, (10 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
The price is €212
includes taxes & fees
10 Dec - 11 Dec
Small Town Lodge - Annapolis, MO Black River

5. Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (41 reviews)
"The cabin was perfect for our needs! It was clean and perfect size and convenient to the Black River and town to get supplies."
United States
Rik B.
The price is €218
includes taxes & fees
10 Dec - 11 Dec
Hillside Cabin #1 Annapolis, MO Black River

6. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
8.0 out of 10, Very good, (7 reviews)
"we had a great stay"
United States
Jasonl C.
The price is €202
includes taxes & fees
10 Dec - 11 Dec
FS Rental #1 Annapolis, MO Black River

7. FS Rental #3 Annapolis, MO Black River

FS Rental #3 Annapolis, MO Black River
Annapolis
8.4 out of 10, Very good, (15 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 €175
includes taxes & fees
10 Dec - 11 Dec
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, (30 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
Hillside Cabin #3 Annapolis, MO Black River

9. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.2 out of 10, Wonderful, (7 reviews)
"Lpleasant environment, beautiful view, the cabin was super clean and enjoyableonly note being the bed was stiff and pillows were thin but overall would recommend"
United States
Teresa C.
The price is €217
includes taxes & fees
11 Nov - 12 Nov
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, (48 reviews)
"Would stay here again"
United States
Steve A.
The price is €126
includes taxes & fees
21 Nov - 22 Nov
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

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

Cozy hobby farm cabin under the stars with treehouse, & hot tub
Patterson
9.6 out of 10, Exceptional, (12 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
The price is €107
includes taxes & fees
23 Nov - 24 Nov
Cozy hobby farm cabin under the stars with treehouse, & hot tub

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

Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool
Arcadia
10.0 out of 10, Exceptional, (1 review)
"Cute bungalow; perfect for me and my husband while in Arcadia to visit family."
United States
Julie H.
The price is €178
includes taxes & fees
11 Nov - 12 Nov
Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool

13. 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 €127
includes taxes & fees
11 Nov - 12 Nov
Sam A Baker State Park

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

Escape to Clearwater Lake and Upper Black River, Pet Friendly
Piedmont
10.0 out of 10, Exceptional, (3 reviews)
"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 €166
includes taxes & fees
11 Nov - 12 Nov
Escape to Clearwater Lake and Upper Black River, Pet Friendly

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

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (34 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
The price is €155
includes taxes & fees
11 Nov - 12 Nov
Lake Road Cabin C — Million Dollar Ozark View!

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

Ironton Hub: Near Elephant Rocks & Shut-Ins
Ironton
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Perfect for the short stay we needed. Clean and convenient. Will recommend."
United States
angie m.
The price is €175
includes taxes & fees
11 Nov - 12 Nov
Ironton Hub: Near Elephant Rocks & Shut-Ins

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
The price is €177
includes taxes & fees
11 Nov - 12 Nov
Ironton Hub: Near Elephant Rocks & Shut-ins

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

Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.
Ironton
9.8 out of 10, Exceptional, (36 reviews)
"This cabin was sooo cozy, and the location was excellent! So quiet and peaceful!Great place to enjoy God's country!"
United States
shirley w.
The price is €294
includes taxes & fees
29 Nov - 30 Nov
Hidden Hollow Cabin. Charming 2-bedroom cabin on a beautiful lake.

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

The Mustard Seed - Cozy Tiny Home in the Ozarks
Patterson
The Mustard Seed - Cozy Tiny Home in the Ozarks

20. 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)
"Ellen is a Very communicative and helpful host. Property looks even better in person than in the pictures. Enjoyable stay!"
United States
Robert H.
The price is €428
includes taxes & fees
11 Nov - 12 Nov
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
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.

Find holiday rentals that suit your style

Find out more about Annapolis

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as €127 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.