Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Fridge, microwave, oven, stovetop
Completely Renovated in May 2023

Cabin in Annapolis

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.
$210 nightly
The price is $210
Dec 2 - Dec 3
Total with taxes and fees
Completely Renovated in May 2023
Fridge, microwave, oven, stovetop
New Cabin Just Minutes from Black River

Cabin in Annapolis

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 2 - Dec 3
Total with taxes and fees
New Cabin Just Minutes from Black River
1 bedroom, bed sheets
RIVER and SKY Cabin; Hot Tub

Cabin in Fredericktown

10.0 out of 10, Exceptional, (2)
"Great getaway"
United States
Anonymous traveler
$238 nightly
The price is $249
Dec 2 - Dec 3
Total with taxes and fees
RIVER and SKY Cabin; Hot Tub
Outdoor dining
Hillside Cabin #1 Annapolis, MO Black River

Cabin in Annapolis

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 2 - Dec 3
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River
Property grounds
Hillside Cabin #2 Annapolis, MO Black River

Cabin in Annapolis

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.
$219 nightly
The price is $219
Dec 2 - Dec 3
Total with taxes and fees
Hillside Cabin #2 Annapolis, MO Black River
Outdoor dining
Completely Renovated in May 2023

Cabin in Annapolis

8.0 out of 10, Very Good, (12)
"Loved the space!!! Ran out of toilet paper but luckily had extra paper towels! Ceiling fan had an annoying drumming noise. Great location, close to eats…liquor locker has great burgers!!!"
United States
Adam W.
$205 nightly
The price is $205
Dec 2 - Dec 3
Total with taxes and fees
Completely Renovated in May 2023
Fridge, microwave, oven, stovetop
Hillside Cabin #5 Annapolis, MO

Cabin in Annapolis

9.2 out of 10, Wonderful, (5)
"Great location and very clean."
United States
Mary C.
$219 nightly
The price is $219
Dec 2 - Dec 3
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
Fridge, microwave, oven, stovetop
Hillside Cabin #3 Annapolis, MO Black River

Cabin in Annapolis

7.8 out of 10, Good, (27)
"Really a nice and clean and cozy stay."
United States
Adam G.
$201 nightly
The price is $201
Dec 2 - Dec 3
Total with taxes and fees
Hillside Cabin #3 Annapolis, MO Black River
Property grounds
5 camper hookups on a beautiful private lake.

Camping in Ironton

1.0 star property
$32 nightly
The price is $32
Dec 2 - Dec 3
Total with taxes and fees
5 camper hookups on a beautiful private lake.
Miscellaneous
Wanderers End Sanctuary Forest Farm & Village Co-op

Camping in Clubb

$65 nightly
The price is $69
Dec 2 - Dec 3
Total with taxes and fees
Wanderers End Sanctuary Forest Farm & Village Co-op
Exterior
The Wyatt Earp

Mobile Home in Black

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.
$265 nightly
The price is $279
Dec 2 - Dec 3
Total with taxes and fees
The Wyatt Earp
Outdoor dining
St Francis River: The Blue Yurt and Hot Tub

Cabin in Fredericktown

8.8 out of 10, Excellent, (18)
"Loved this rental - great property!"
United States
Julie S.
$195 nightly
The price is $204
Dec 2 - Dec 3
Total with taxes and fees
St Francis River: The Blue Yurt and Hot Tub
1 bedroom, WiFi, bed sheets
Cozy train caboose with cupola loft and firepit-Sleeps 4

Apartment in Fredericktown

2.0 star property
$203 nightly
The price is $203
Dec 2 - Dec 3
Total with taxes and fees
Cozy train caboose with cupola loft and firepit-Sleeps 4
Outdoor pool
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool

Mobile Home in Fredericktown

2.0 star property
$267 nightly
The price is $267
Dec 31 - Jan 1, 2026
Total with taxes and fees
Charming 2-bedroom country mobile home with game room, hot tub, seasonal pool
Cabin
Sam A Baker State Park

Cabin in Patterson

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 2 - Dec 3
Total with taxes and fees
Sam A Baker State Park
Property grounds
By Everything, Away from it all! Wi-Fi camping in Iron County

Camping in Ironton

2.0 out of 10, (1)
"No tent. No contact response from owners after multiple calls and texts. Nothing was set up. There was no tent it was a scam. Looking for my money back. Do not make the same mistake. My wife and daughter were not happy thus I was furious. Still looking for this loser for refund. "
United States
Ryan O.
$129 nightly
The price is $139
Dec 2 - Dec 3
Total with taxes and fees
By Everything, Away from it all! Wi-Fi camping in Iron County
Exterior
The Linkin: a cozy mountain cabin w/ king bed

Cabin in Ironton

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.
$280 nightly
The price is $295
Dec 2 - Dec 3
Total with taxes and fees
The Linkin: a cozy mountain cabin w/ king bed
Interior
AV Bungalows #9A with Loft

Vacation Home in Arcadia

10.0 out of 10, Exceptional, (1)
"Amenities were great, house was perfect for our group, and easy access to local state parks."
United States
Allen D.
$331 nightly
The price is $355
Dec 2 - Dec 3
Total with taxes and fees
AV Bungalows #9A with Loft
1 bedroom, iron/ironing board, WiFi, bed sheets
The King Suite at Pickle & Perk

Aparthotel in Ironton

10.0 out of 10, Exceptional, (2)
"Jrrat people and just beautifully decorated. "
United States
Tamara S.
$179 nightly
The price is $179
Dec 2 - Dec 3
Total with taxes and fees
The King Suite at Pickle & Perk
Property grounds
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

Vacation Home in Ironton

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.
$243 nightly
The price is $243
Dec 2 - Dec 3
Total with taxes and fees
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
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
"Good breakfast and parking "
Joe 2-night trip
Posted 7 days 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 $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.

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?

Just Minutes from Black River – With WIFI: 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 Walnut Hollow Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Taum Sauk Mountain State Park and K Bridge Recreation Area 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.