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Top Holiday Rentals in Annapolis

Exterior
Hillside Cabin #4 Annapolis, MO Black River
9.6 out of 10, Exceptional, (29)
"Nice new cabin, looks exactly like the pictures. We enjoyed our stay and the host was awesome!"
The price is £221
includes taxes & fees
23 Jun - 24 Jun
Hillside Cabin #4 Annapolis, MO Black River
Fridge, microwave, oven, stovetop
FS Cabin #1 - 5mins to Black River
The price is £207
includes taxes & fees
28 May - 29 May
FS Cabin #1 - 5mins to Black River
Exterior
Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (58)
"We had a lovely time at the cabin! We stayed for the total eclipse and enjoyed a quiet private viewing in the woods! Our two little dogs were very happy at the property. The road leading down is a little bit rough, but that is the last 3 mile leg of the journey. You can hike up a nearby hill for cell reception if you need to connect, but the best part of this cabin was unplugging and relaxing. The short walk down the road leads to the large gravel riverbank. Fun for fossil hunting, skipping...
Rustic River Cabin Getaway
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Fridge, microwave, oven, stovetop
Hillside Cabin #5 Annapolis, MO
10.0 out of 10, Exceptional, (3)
"Absolutely lovely! Close to the Black River, which was where we floated. It was a very nice cabin"
The price is £171
includes taxes & fees
26 May - 27 May
Hillside Cabin #5 Annapolis, MO
Outdoor dining
Relaxing 3B Cabin-15 min walk to the Black River!
9.6 out of 10, Exceptional, (7)
"We had a family trip with 8 adults and 7 kids, ages from 2 to 16. It was a perfect trip. The cabin had everything you would need for cooking indoors or outside. The kids had a great time playing outside and inside with board games and a huge selection of movies. The adults had a great time catching up together, around the fire and around the dinner table. Loved the decor and the cozy places to sit around in every corner of the cabin. The porch in front with coffee was so nice, listening to the...
Relaxing 3B Cabin-15 min walk to the Black River!
Fridge, microwave, oven, stovetop
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, (24)
"Really a nice and clean and cozy stay."
The price is £173
includes taxes & fees
28 May - 29 May
Hillside Cabin #3 Annapolis, MO Black River
Outdoor dining
FS Cabin #3 Brand New - 5 mins to Black River
7.6 out of 10, Good, (4)
"Cabin very clean, comfy beds, great kitchen area with nice pots and dishes, cute little porch. Also Thank you Justin for mailing my straightener that I forgot was in bathroom cabinet! Remembered when we were already about hour on road. Overall, highly recommend this great VRBO!"
The price is £179
includes taxes & fees
27 May - 28 May
FS Cabin #3 Brand New - 5 mins to Black River
Dining
FS Cabin #4 - Close to Black River
8.0 out of 10, Very good, (1)
"We did enjoy staying here. Clean and cozy. Was a little thrown off that it was 20 ft from railroad tracks though."
The price is £161
includes taxes & fees
26 May - 27 May
FS Cabin #4 - Close to Black River
Property grounds
Hillside Cabin #2 Annapolis, MO Black River
9.6 out of 10, Exceptional, (54)
"Great !!!!"
The price is £183
includes taxes & fees
28 May - 29 May
Hillside Cabin #2 Annapolis, MO Black River
Property grounds
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
9.8 out of 10, Exceptional, (9)
"We stayed here because of an event we were attending. This was the perfect location for us."
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
Fridge, microwave, oven, coffee/tea maker
Spring Street Cabin #2
9.0 out of 10, Wonderful, (2)
"Plenty of privacy and everything you need. The owner was great at communicating."
The price is £174
includes taxes & fees
4 Jun - 5 Jun
Spring Street Cabin #2
Exterior
Hillside Cabin #1 Annapolis, MO Black River
9.6 out of 10, Exceptional, (35)
"Everything was great, everyone felt comfortable and safe. Everything we needed was there including shampoo, conditioner, and bath soap. We cooked out and used the fire pit, both were great. Everything was clean. We went floating and that was very close. Anything we needed was very close, we wanted for nothing. Highly recommend staying there."
The price is £197
includes taxes & fees
20 Jun - 21 Jun
Hillside Cabin #1 Annapolis, MO Black River
1 bedroom, free WiFi, bed sheets
Panther Den Cabin is located 4 miles from Hwy K Campground
9.4 out of 10, Exceptional, (10)
"Overall really enjoyed the stay and natural beauty, however not being able to flush toilet paper was definitely a downside"
Panther Den Cabin is located 4 miles from Hwy K Campground
Smart TV
Small Town Lodge - Black River
The price is £251
includes taxes & fees
26 May - 27 May
Small Town Lodge - Black River
Pool
River front property HOT TUB, Kayak, tubing, and fishing
9.6 out of 10, Exceptional, (70)
"A little difficult to find. Other wise great. "
The price is £220
includes taxes & fees
28 May - 29 May
River front property HOT TUB, Kayak, tubing, and fishing
Exterior
Lake Road Cabin C — Million Dollar Ozark View!
10.0 out of 10, Exceptional, (11)
"This served as a perfect base of operations for visiting the Shut Ins and seeing Ironton’s Mountain Music Festival. Being on the backside of Shepard Mountain it’s super quiet and separated from the world… but town is only a few minutes away around on the other side of the base of the mountain. It had everything you would want in an experience if you were camping, like a fire pit, endless stars, and all the quiet of being remote in the forest alone…. But inside it’s nice the cabin , clean,...
The price is £165
includes taxes & fees
9 Jun - 10 Jun
Lake Road Cabin C — Million Dollar Ozark View!
Fridge, microwave, stovetop, dishwasher
Cozy Lesterville Home Near Parks & Forests!
10.0 out of 10, Exceptional, (9)
"Had a great weekend getaway to float the Black River. Used black river camp ground. This was our second year staying at this vrbo. Great location! Great house!! Highly recommend!"
Cozy Lesterville Home Near Parks & Forests!
Outdoor pool
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
10.0 out of 10, Exceptional, (51)
"We came with our whole family for a family vacation. We definitely enjoyed our time there even with three toddlers. The property is well cleaned and taken care of. My toddler’s favorite things to do during our stay was saying hi to the pony every morning, swimming, and playing with the neighbor dogs outside."
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Fridge, microwave, oven, stovetop
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
10.0 out of 10, Exceptional, (4)
"perfect location and very private place."
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
Microwave, oven, stovetop, dishwasher
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
10.0 out of 10, Exceptional, (4)
"We cane for the total eclipse and couldn’t have picked a better place. The community is friendly, the parks are fun and the house was the oerfect balance of old and new. The beds are comfortable and the firepit makes for great storytelling and s’mores. Highly recommend."
The price is £408
includes taxes & fees
27 May - 28 May
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
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See all available properties in Annapolis
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.

Annapolis Holiday Rental Travel Info

Other types of properties in Annapolis you may be interested in

Fridge, microwave, oven, stovetop
Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, (24)
"Really a nice and clean and cozy stay."
The price is £173
includes taxes & fees
28 May - 29 May
Hillside Cabin #3 Annapolis, MO Black River
Exterior
Hillside Cabin #4 Annapolis, MO Black River
9.6 out of 10, Exceptional, (29)
"Nice new cabin, looks exactly like the pictures. We enjoyed our stay and the host was awesome!"
The price is £221
includes taxes & fees
23 Jun - 24 Jun
Hillside Cabin #4 Annapolis, MO Black River
Exterior
Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (58)
"We had a lovely time at the cabin! We stayed for the total eclipse and enjoyed a quiet private viewing in the woods! Our two little dogs were very happy at the property. The road leading down is a little bit rough, but that is the last 3 mile leg of the journey. You can hike up a nearby hill for cell reception if you need to connect, but the best part of this cabin was unplugging and relaxing. The short walk down the road leads to the large gravel riverbank. Fun for fossil hunting, skipping...
Rustic River Cabin Getaway
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.

Everything you need to know about Annapolis holiday rentals

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

Annapolis holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as £161 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday 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 holiday.

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 holiday rental in Annapolis?

Yes, there are holiday rentals close to the most popular sights in Annapolis, or you can select a more secluded option if you're looking for a relaxing 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.

How many holiday rentals are there in Annapolis?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Annapolis stay.

What can I see and do in Annapolis?

Taum Sauk Mountain State Park and Mark Twain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, K Bridge Recreation Area and Walnut Hollow Lake are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.

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