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Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (60 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.
$231 nightly
The price is $231
Jun 30 - Jul 1
Total with taxes and fees
Hillside Cabin #2 Annapolis, MO Black River

Secluded Log Cabin

Secluded Log Cabin
Annapolis
9.8 out of 10, Exceptional, (28 reviews)
"Stay was fine, nice peaceful setting, enjoyed our stay and would come back or recommend to others, thank you"
United States
Glen J.
$198 nightly
The price is $211
Jul 6 - Jul 7
Total with taxes and fees
Secluded Log Cabin

FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (7 reviews)
"This was a great place to stay, so close to my job site. Comfortable, clean and well furnished. I would definitely stay here again!"
United States
Steven G.
$230 nightly
The price is $230
Jun 28 - Jun 29
Total with taxes and fees
FS Rental #4 Annapolis, MO Black River

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.
$229 nightly
The price is $229
Jun 28 - Jun 29
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO

RIVER and SKY Cabin; Hot Tub

RIVER and SKY Cabin; Hot Tub
Fredericktown
9.0 out of 10, Wonderful, (4 reviews)
"Great getaway"
United States
Anonymous traveler
$238 nightly
The price is $252
Jun 30 - Jul 1
Total with taxes and fees
RIVER and SKY Cabin; Hot Tub

Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (38 reviews)
"The cabin was exactly like the pictures showed. It worked out perfectly for our family with just enough room to spread out, and with a large main area that we could hang out together comfortably. We took advantage of the spacious patio and enjoyed a fire each night. I would definitely stay again."
United States
Amy A.
$291 nightly
The price is $291
Jun 28 - Jun 29
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
9.0 out of 10, Wonderful, (7 reviews)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
$303 nightly
The price is $303
Jun 28 - Jun 29
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River
Annapolis
7.8 out of 10, Good, (27 reviews)
"Really a nice and clean and cozy stay."
United States
Adam G.
$219 nightly
The price is $219
Jun 28 - Jun 29
Total with taxes and fees
Hillside Cabin #3 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River

FS Rental #1 Annapolis, MO Black River
Annapolis
7.6 out of 10, Good, (5 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.
$266 nightly
The price is $266
Jun 28 - Jun 29
Total with taxes and fees
FS Rental #1 Annapolis, MO Black River

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.
$230 nightly
The price is $230
Jun 28 - Jun 29
Total with taxes and fees
FS Rental #3 Annapolis, MO Black River

Cozy hobby farm cabin under the stars!

Cozy hobby farm cabin under the stars!
Greenville
10.0 out of 10, Exceptional, (5 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
Jun 26 - Jun 27
Total with taxes and fees
Cozy hobby farm cabin under the stars!

Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (27 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
$168 nightly
The price is $179
Jun 28 - Jun 29
Total with taxes and fees
Lake Road Cabin C — Million Dollar Ozark View!

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, (39 reviews)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
$140 nightly
The price is $147
Jun 26 - Jun 27
Total with taxes and fees
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

St Francis River: The Blue Yurt and Hot Tub

St Francis River: The Blue Yurt and Hot Tub
Fredericktown
8.6 out of 10, Excellent, (24 reviews)
"Loved this rental - great property!"
United States
Julie S.
$196 nightly
The price is $212
Jun 29 - Jun 30
Total with taxes and fees
St Francis River: The Blue Yurt and Hot Tub

Johnson's Shut-ins State Park

Johnson's Shut-ins State Park
3.0 star property
Middle Brook
10.0 out of 10, Exceptional, (3 reviews)
"Nice property"
United States
Aleksandr
$266 nightly
The price is $281
Jun 28 - Jun 29
Total with taxes and fees
Johnson's Shut-ins State Park

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

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (37 reviews)
"Great place to stay!"
United States
Derek R.
$262 nightly
The price is $275
Jul 14 - Jul 15
Total with taxes and fees
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

The Linkin: a cozy mountain cabin w/ king bed

The Linkin: a cozy mountain cabin w/ king bed
Ironton
10.0 out of 10, Exceptional, (12 reviews)
"Amazing location. Very remote but if you like that then this is the location for you"
United States
Joshua P.
$303 nightly
The price is $320
Jun 30 - Jul 1
Total with taxes and fees
The Linkin: a cozy mountain cabin w/ king bed

Mountain View at Pickle & Perk

Mountain View at Pickle & Perk
Ironton
10.0 out of 10, Exceptional, (23 reviews)
"Our stay was excellent. The rooms were cozy and a perfect location to get to Elephant Rock and Johnson Shut-Ins."
United States
Cara J.
$192 nightly
The price is $208
Jun 29 - Jun 30
Total with taxes and fees
Mountain View at Pickle & Perk

Secluded Private Beautiful Cabin in Mill Spring MO

Secluded Private Beautiful Cabin in Mill Spring MO
Mill Spring
$153 nightly
The price is $161
Jun 27 - Jun 28
Total with taxes and fees
Secluded Private Beautiful Cabin in Mill Spring MO

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
Jun 29 - Jun 30
Total with taxes and fees
AV Bungalows #9B
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

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. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. 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.