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Annapolis Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Annapolis vacation 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

FS Rental #4 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (10 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
$208 nightly
The price is $208
Oct 20 - Oct 21
Total with taxes and fees
FS Rental #4 Annapolis, MO Black River
A cabin interior with a loft bed, a chair, and a ceiling fan.

2. Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (65 reviews)
"The cabin was very nice but looks a little un loved. 6 nights no tv in the evening and no reply. Looks like no one is doing up keep on the place. We did love how close we were to the river and the store. Very quite and private property. Shower curtain had a lot of mildew build up. Would give it 4 stars if it was cleaner and everything worked."
United States
Tim S.
$217 nightly
The price is $217
Oct 20 - Oct 21
Total with taxes and fees
Hillside Cabin #2 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.

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.
$217 nightly
The price is $217
Oct 20 - Oct 21
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
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
8.4 out of 10, Very good, (9 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
$251 nightly
The price is $251
Oct 20 - Oct 21
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River
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

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
$252 nightly
The price is $252
Oct 20 - Oct 21
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River
Living Room & Dining Area

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 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.
$233 nightly
The price is $233
Oct 20 - Oct 21
Total with taxes and fees
FS Rental #1 Annapolis, MO Black River
A modern room with a large window, two chairs, a small wooden table, and a view of a forest.

7. RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.4 out of 10, Exceptional, (6 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.
$236 nightly
The price is $250
Oct 29 - Oct 30
Total with taxes and fees
RIVER and SKY Cabin; Hot Tub
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
8.4 out of 10, Very good, (14 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.
$203 nightly
The price is $203
Oct 20 - Oct 21
Total with taxes and fees
FS Rental #3 Annapolis, MO Black River
A wooden deck with chairs and a fire pit in a forested area.

9. 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.
$199 nightly
The price is $199
Nov 8 - Nov 9
Total with taxes and fees
Hillside Cabin #3 Annapolis, MO Black River
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, (48 reviews)
"Would stay here again"
United States
Steve A.
$140 nightly
The price is $147
Oct 20 - Oct 21
Total with taxes and fees
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
A rustic log cabin with a stone foundation, surrounded by trees and a wooden fence.

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
$150 nightly
The price is $159
Oct 25 - Oct 26
Total with taxes and fees
Sam A Baker State Park
A modern kitchen with dark cabinetry, a stainless steel refrigerator, a wooden dining table, and a clock on the wall.

12. 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, (2 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.
$182 nightly
The price is $191
Oct 20 - Oct 21
Total with taxes and fees
Ride Trails or go fishing near Clearwater lake. No cleaning fees, pet friendly
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, (32 reviews)
"Great cabin. Very quiet area. Nice fire pit."
United States
Heather the Librarian
$169 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
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
3.0 star property
Ironton
$180 nightly
The price is $196
Oct 20 - Oct 21
Total with taxes and fees
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
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.
$115 nightly
The price is $121
Nov 2 - Nov 3
Total with taxes and fees
Cozy hobby farm cabin under the stars!
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 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.
$183 nightly
The price is $198
Oct 20 - Oct 21
Total with taxes and fees
Ironton Hub: Near Elephant Rocks & Shut-Ins
A bedroom with a bed, a bench, and a ceiling fan.

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.
$155 nightly
The price is $167
Oct 25 - Oct 26
Total with taxes and fees
AV Bungalows #9B
A dining area with a table and chairs, wooden cabinets, and a kitchen with an archway.

18. 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.
$479 nightly
The price is $503
Oct 20 - Oct 21
Total with taxes and fees
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

19. Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (30 reviews)
"Perfect getaway, great experience. Hosts are phenomenal, food and coffee drinks are excellent. Highly recommend."
United States
Anonymous traveler
$191 nightly
The price is $207
Oct 20 - Oct 21
Total with taxes and fees
Mountain View at Pickle & Perk
A hot tub in a covered outdoor area with a view of a swimming pool and a wooden play structure in the background.

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
10.0 out of 10, Exceptional, (14 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
$200 nightly
The price is $212
Oct 20 - Oct 21
Total with taxes and fees
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
"Easy location and next to great BBQ restaurant. Comfortable beds, clean room, coffee and fridge in room and free hot breakfast served near lobby. Pretty creek behind hotel. Staff was friendly and very helpful. Property decorated with beautiful flowers and room was decorated with flowers too. We were hiking and staff offered great suggestions. Would definitely stay again when visiting this area."
Patti 1-night trip
Posted 3 weeks ago
Shepherd Mountain Inn

Find out more about Annapolis

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation 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 low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.