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Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
9.6 out of 10, Exceptional, (8 reviews)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
$210 nightly
The price is $210
Sep 11 - Sep 12
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
9.2 out of 10, Wonderful, (62 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.
$219 nightly
The price is $219
Sep 11 - Sep 12
Total with taxes and fees
Hillside Cabin #2 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
$254 nightly
The price is $254
Sep 11 - Sep 12
Total with taxes and fees
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.
$254 nightly
The price is $254
Sep 13 - Sep 14
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River

5. FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
8.0 out of 10, Very Good, (6 reviews)
$236 nightly
The price is $236
Sep 12 - Sep 13
Total with taxes and fees
FS Rental #1 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.

6. 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.
$220 nightly
The price is $220
Sep 13 - Sep 14
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
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.
$200 nightly
The price is $200
Sep 11 - Sep 12
Total with taxes and fees
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.
$205 nightly
The price is $205
Sep 11 - Sep 12
Total with taxes and fees
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 traveler
$239 nightly
The price is $253
Sep 3 - Sep 4
Total with taxes and fees
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.
$140 nightly
The price is $147
Sep 3 - Sep 4
Total with taxes and fees
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
A cozy cabin-style room with a wooden interior, a sofa, a dining table, and a kitchen area.

11. Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Greenville
10.0 out of 10, Exceptional, (9 reviews)
"Easy check in, very quiet, very calming and relaxing. Overall great stay and great property manager. "
United States
Wyatt S.
$114 nightly
The price is $120
Sep 9 - Sep 10
Total with taxes and fees
Cozy hobby farm cabin under the stars!
A kitchen with wooden cabinets, a toaster, and a dishwasher.

12. 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)
"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
$170 nightly
The price is $181
Sep 3 - Sep 4
Total with taxes and fees
Lake Road Cabin C — Million Dollar Ozark View!
A porch with four green Adirondack chairs, a small table, and string lights.

13. *State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (40 reviews)
"Great place to stay!"
United States
Derek R.
$261 nightly
The price is $273
Sep 3 - Sep 4
Total with taxes and fees
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
A room with a black sectional sofa, a wooden coffee table, and two side tables with lamps.

14. Cozy Cabin sleeps 4 near Clearwater Lake and Upper Black River

Cozy Cabin sleeps 4 near Clearwater Lake and Upper Black River
Piedmont
$181 nightly
The price is $190
Sep 3 - Sep 4
Total with taxes and fees
Cozy Cabin sleeps 4 near Clearwater Lake and Upper Black 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.

15. 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.
$201 nightly
The price is $218
Sep 3 - Sep 4
Total with taxes and fees
Ironton Hub: Near Elephant Rocks & Shut-Ins
A rustic log cabin with a stone foundation, surrounded by trees and a wooden fence.

16. 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
$195 nightly
The price is $207
Sep 3 - Sep 4
Total with taxes and fees
Sam A Baker State Park
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
Sep 3 - Sep 4
Total with taxes and fees
AV Bungalows #9B
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, (28 reviews)
"Perfect getaway, great experience. Hosts are phenomenal, food and coffee drinks are excellent. Highly recommend."
United States
Anonymous traveler
$192 nightly
The price is $208
Sep 3 - Sep 4
Total with taxes and fees
Mountain View at Pickle & Perk
A modern kitchen with dark cabinets, a built-in microwave, a flat-screen TV, and a large window with a view of the street.

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

Ironton Hub: Near Elephant Rocks & Shut-ins
3.0 star property
Ironton
$200 nightly
The price is $218
Sep 3 - Sep 4
Total with taxes and fees
Ironton Hub: Near Elephant Rocks & Shut-ins
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.

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.
$483 nightly
The price is $507
Sep 3 - Sep 4
Total with taxes and fees
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.
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Top Annapolis Hotel Reviews

Madison Inn Lodge

Madison Inn Lodge

10/10 Excellent
"Nice and clean friendly staff"
Bawan 1-night trip
Posted 22 hours ago
Madison Inn Lodge

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 $129 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?

Mark Twain National Forest and K Bridge Recreation Area 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.