Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

9.4 out of 10, Exceptional, (59)
"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.
$220 nightly
The price is $220
Dec 26 - Dec 27
Total with taxes and fees
Hillside Cabin #2 Annapolis, MO Black River
9.2 out of 10, Wonderful, (5)
"Great location and very clean."
United States
Mary C.
$220 nightly
The price is $220
Dec 26 - Dec 27
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
9.0 out of 10, Wonderful, (7)
"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
Dec 26 - Dec 27
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River
9.6 out of 10, Exceptional, (7)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
$211 nightly
The price is $211
Dec 26 - Dec 27
Total with taxes and fees
FS Rental #4 Annapolis, MO Black River
9.4 out of 10, Exceptional, (36)
"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.
$255 nightly
The price is $255
Dec 26 - Dec 27
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River

Cabin in Fredericktown

RIVER and SKY Cabin; Hot Tub
10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveler
$236 nightly
The price is $247
Jan 4 - Jan 5, 2026
Total with taxes and fees
RIVER and SKY Cabin; Hot Tub
8.0 out of 10, Very Good, (12)
"Enjoyed our stay. Our 2nd time staying here for our canoe trip. Patio area is nice for relaxing outside also. Canoe rental place Jeff's canoe only about 8 min away. And Iron Mule and Thee Abby Kitchen nice place to eat. "
United States
Denise R.
$206 nightly
The price is $206
Dec 28 - Dec 29
Total with taxes and fees
FS Rental #3 Annapolis, MO Black River
1.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to enjoy camping"
United States
ChangHee S.
$32 nightly
The price is $32
Dec 26 - Dec 27
Total with taxes and fees
5 camper hookups on a beautiful private lake.

Mobile Home in Black

The Wyatt Earp
10.0 out of 10, Exceptional, (1)
"My family wanted to visit Johnson shut-in’s and I found this place to stay at it was perfect for us."
United States
Angela S.
$269 nightly
The price is $283
Dec 26 - Dec 27
Total with taxes and fees
The Wyatt Earp
$65 nightly
The price is $69
Dec 26 - Dec 27
Total with taxes and fees
Wanderers End Sanctuary Forest Farm & Village Co-op
8.8 out of 10, Excellent, (18)
"Loved this rental - great property!"
United States
Julie S.
$199 nightly
The price is $208
Dec 28 - Dec 29
Total with taxes and fees
St Francis River: The Blue Yurt and Hot Tub
2.0 star property
$203 nightly
The price is $203
Dec 28 - Dec 29
Total with taxes and fees
Cozy train caboose with cupola loft and firepit-Sleeps 4

Cabin in Patterson

Sam A Baker State Park
2.0 star property
9.2 out of 10, Wonderful, (5)
"Pet friendly, great staff. "
United States
Charlie
$125 nightly
The price is $132
Dec 28 - Dec 29
Total with taxes and fees
Sam A Baker State Park
10.0 out of 10, Exceptional, (33)
"Very friendly, helpful host, clean and cute house. Love the area for shops, and hiking we had a wonderful stay!"
United States
beth s.
$238 nightly
The price is $250
Jan 5 - Jan 6, 2026
Total with taxes and fees
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
10.0 out of 10, Exceptional, (10)
"Amazing location. Very remote but if you like that then this is the location for you"
United States
Joshua P.
$279 nightly
The price is $294
Dec 30 - Dec 31
Total with taxes and fees
The Linkin: a cozy mountain cabin w/ king bed
10.0 out of 10, Exceptional, (24)
"Girls weekend enjoyed our time. Just a great little cabin so we could enjoy the parks!"
United States
Jeanine H.
$149 nightly
The price is $158
Dec 26 - Dec 27
Total with taxes and fees
Lake Road Cabin C — Million Dollar Ozark View!

Vacation Home in Ironton

Charming 1860s Renovated Home
8.0 out of 10, Very Good, (17)
"Check in was easy. Very spacious house and clean. We were able to sleep 9 comfortably. "
United States
Samantha P.
$272 nightly
The price is $272
Dec 26 - Dec 27
Total with taxes and fees
Charming 1860s Renovated Home
10.0 out of 10, Exceptional, (45)
"Adorable house with everyone you need provided! Super clean and the beds were very comfy. Will stay here again on our next trip to the area. "
United States
Brandi
$142 nightly
The price is $160
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Sutton House 2 blocks from Main Street & Courthouse Square

Apartment in Ironton

Mountain View at Pickle & Perk
2.5 star property
10.0 out of 10, Exceptional, (19)
"Very cute place in beautiful area. Easy check-in, clean home, and comfy bed. The coffee shop below was really good with a beautiful patio. Location was perfect to access Elephant Rocks, Johnson Shut-ins, and Taum Sauk Mountain parks. "
United States
Amber S.
$182 nightly
The price is $191
Jan 1 - Jan 2, 2026
Total with taxes and fees
Mountain View at Pickle & Perk

Apartment in Ironton

Pickleball Cafe & Micro Hotel
10.0 out of 10, Exceptional, (19)
"The perfect combination of quaint and modern! Loved the decor and getting to enjoy dinner on the porch outside overlooking the patio. Would definitely stay again!"
United States
Alexandra Z.
$196 nightly
The price is $207
Jan 3 - Jan 4, 2026
Total with taxes and fees
Pickleball Cafe & Micro Hotel
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 $132 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.

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?

FS Rental #2 Annapolis, MO Black River: Visitors give good reviews to this Annapolis vacation home rental, which is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, an oven, and a microwave.

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.