Annapolis Vacation Rentals

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Browse Select Annapolis Vacation Homes

Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
10.0 out of 10, Exceptional, (20)
"We really enjoyed our stay! The house is as pictured - beautiful and comfortable - and the location is perfectly convenient to the cute shops, coffee, and restaurants of downtown Ironton, as well as the area attractions like Elephant Rocks, Johnson's Shut-Ins, etc. We'll definitely come back! "
The price is CA $178
CA $319 total
includes taxes & fees
Sep 29 - Sep 30
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
Enjoy a charming 1860s newly renovated home!!
7.6 out of 10, Good, (8)
"The house was perfect for our friends. Host did not respond to a question about what type of coffee maker but they had a great coffee bar setup when we arrived."
The price is CA $182
CA $362 total
includes taxes & fees
Sep 29 - Sep 30
Enjoy a charming 1860s newly renovated home!!
Newly remodeled offers many amenities with perfect location!
10.0 out of 10, Exceptional, (21)
"We had a WONDERFUL long weekend stay and highly recommend this house! Our hosts, Toni and Jim, took great care in creating a welcoming environment. The house is well cared for, clean, comfortable, and the details of the house made us feel right at home! The location is also wonderful - so close to great hiking and views. We hope to return in the near future, and we recommend this to others as well!"
Newly remodeled offers many amenities with perfect location!
Charming Bungalow. Children and Pet Friendly.
10.0 out of 10, Exceptional, (8)
"This home is perfect for a family getaway. It's charming and well cared for, with many thoughtful touches and amenities throughout. Our kids loved having their own space upstairs to sleep and play. This is a perfect location for Elephant Rocks, Johnson Shut-ins, Taum Sauk, floating, the Bonne Terre mines, and much more. Thank you for a great stay!"
Charming Bungalow. Children and Pet Friendly.
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
9.6 out of 10, Exceptional, (9)
"We rented the space so that we could float nearby during the day and have a place to stay overnight that included AC+Showers for folks who were not into the idea of tent camping. The house itself is very spacious and outside there were many different areas to gather and chill . It’s also nice having a full kitchen to cook and hangout in. Overall, you can tell a lot of work was put into making this the perfect getaway. One thing to note- the description says it fits 8 but sleeps 6. We were a bit...
The price is CA $404
CA $683 total
includes taxes & fees
Sep 28 - Sep 29
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Secluded Gate House
10.0 out of 10, Exceptional, (15)
"Very peaceful property with lots of pleasant surprises - walking trails, horseshoe pits, basketball court. Our family really enjoyed our stay and look forward to returning someday. Had a few questions upon check in and host was very responsive and answered within minutes. Overall pleasant experience."
Secluded Gate House
Sunshine Shack at Clearwater Lake (sleeps 6)
8.8 out of 10, Excellent, (10)
"Loved staying a week at Sunshine Shack. The screened in deck is perfect to watch the deer at dusk."
Sunshine Shack at Clearwater Lake (sleeps 6)
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
10.0 out of 10, Exceptional, (58)
"Our family rented Bluebird Meadows for a weekend get away. We had a great time all three days. Place was everything we were hoping. "
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Rustic Ironton Home w/ Deck & Fire Pit on Creek!
9.8 out of 10, Exceptional, (54)
"Great location, on a creek with good fishing and near several state parks"
Rustic Ironton Home w/ Deck & Fire Pit on Creek!
Cozy Lesterville Home Near Parks & Forests!
10.0 out of 10, Exceptional, (10)
"Was wonderful. Lots of space, nice bathroom, well stocked kitchen for cooking. A little challenging to find the turn the first time but after that easy to get to. Went floating on Black River and it was perfect to be able to have a bed and shower before and after. Will be back again!"
Cozy Lesterville Home Near Parks & Forests!
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay and highly recommend it if you are wanting and relaxing and enjoyable stay "
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
10.0 out of 10, Exceptional, (10)
"We came here going to the black river. We have always stayed at the black river. This is the first time here, it was amazing. Spacious, beautiful views, and plenty to do. I would recommend over And over. This is a great property., we will stay again."
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
Spacious & Secluded Shook Home w/ Private Hot Tub!
10.0 out of 10, Exceptional, (2)
"We loved our stay at Lost Creek Bluebird. We didn't expect the commute to the marina but loved the seclusion of the house. We had some of our family come in from St. Louis and some came from NE Arkansas and the house was a perfect meeting place where we were all under one roof. We played games, roasted marshmallows, made cupcakes and just enjoyed each others company."
Spacious & Secluded Shook Home w/ Private Hot Tub!
Rustic Cabin in Hunters' Paradise!
9.8 out of 10, Exceptional, (25)
"This house worked great for two families for the weekend! It’s a short drive to town and convenient for both the lake and River. The kids brought balls and enjoyed volleyball and soccer in the large flat yard! It’s in the woods so we used a lot of big spray, but that’s expected. Owners were very responsive via text and helpful. We would love to stay again in the future."
Rustic Cabin in Hunters' Paradise!
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
9.6 out of 10, Exceptional, (11)
"The property is located right in town. Easy to get to & parking was fine. Had a water problem in town when we got there but the owner Bobby was making every effort to make sure we were going to be fine. It all worked out by the evening time. It was nice to have the accommodations large enough for our party so we could all be together and play games and sit around the bonfire and talk. Great weekend. I would recommend it for others & will be back another time!"
7 min to K Bridge Black River Annapolis MO Close to Clearwater Lake Piedmont
Spring Street Cabin #2
6.8 out of 10, (3)
"I was pretty disappointed with my experience. We booked and paid for this stay up front. The Tuesday before our stay the host told us the unit was being repaired and that it might not be done for our Friday night stay. We were not contacted prior to this. Turns out the property would be completed and we could still come for our stay. I appreciated the communication up until that point. When we arrived the unit seemed ready. However, there was no central air. There was a window unit in the...
The price is CA $131
CA $256 total
includes taxes & fees
Sep 29 - Sep 30
Spring Street Cabin #2
Clearwater Lake and Black River Vacation Home
9.6 out of 10, Exceptional, (17)
"Nice clean property! Comfortable beds plenty of seating. "
Clearwater Lake and Black River Vacation Home
Serene Belgrade Hideaway with Fire Pit & Grill!
9.0 out of 10, Wonderful, (2)
"Our stay at the Belgrade getaway was stunning in every way. Lovely surroundings with nearby National Forest hiking and rockhounding venues all around. The house was fully equipped and immaculately clean. The only ding was that we couldn't get the TV to work for more than a few minutes due to losing connectivity with their server. We weren't there to watch TV, though, so that was a very minor issue."
Serene Belgrade Hideaway with Fire Pit & Grill!
Secluded Log Cabin - Total privacy
9.8 out of 10, Exceptional, (19)
"Family of 5; we all loved it! Kids even unplugged & spent time w/ the grownups! Robin communicated to us about an issue prior to arrival, but it was all fixed and we had no troubles. Loved that the cabin is away from other homes. Beautiful setting. Cows weren't any trouble, didn't have smells either and they were in the pasture. Possibly because it's November. I didn't see mixing bowls or a wire whisk, but everything else was supplied. Wonderful selection of videos & games. Great weekend;...
Secluded Log Cabin - Total privacy
Charming 2-bedroom house in delightful Ellington with WiFi, AC, private big yard
2.0 star property
The price is CA $162
CA $260 total
includes taxes & fees
Oct 3 - Oct 4
Charming 2-bedroom house in delightful Ellington with WiFi, AC, private big yard
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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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Other property types in Annapolis

Hillside Cabin #3 Annapolis, MO Black River
8.0 out of 10, Very good, (25)
"Really a nice and clean and cozy stay."
The price is CA $138
CA $265 total
includes taxes & fees
Sep 29 - Sep 30
Hillside Cabin #3 Annapolis, MO Black River
Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (68)
"This was our second time staying here. We are going to makenit an annual trip. Love the beach area and love the porch!!!"
Rustic River Cabin Getaway
Hillside Cabin #2 Annapolis, MO Black River
9.4 out of 10, Exceptional, (55)
"Great !!!!"
The price is CA $160
CA $291 total
includes taxes & fees
Sep 28 - Sep 29
Hillside Cabin #2 Annapolis, MO Black 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.