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Compare 23 Vacation Homes in Annapolis with updated reviews, rates, and availability.

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

Enjoy a charming 1860s newly renovated home!!

8.2 out of 10, Very Good, (13)
"Traveling with a large family is never easy, but this rental made us feel at home. Full kitchen for cooking, dining area to seat everyone, huge tv, great wi-fi, washer and dryer, fun backyard to make s’mores, and beds upstairs to sleep all our kids. We would stay here again!"
The price is SAR 507
SAR 1,007 total
includes taxes & fees
25 Dec - 26 Dec
Enjoy a charming 1860s newly renovated home!!

Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

10.0 out of 10, Exceptional, (12)
"Great accommodations for a family, lots of room. No wifi, tho."
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Charming Bungalow. Children and Pet Friendly.

10.0 out of 10, Exceptional, (11)
"We all loved the neat upstairs bedroom! The back yard was big and the kids really enjoyed playing out there. We all thought the beds were comfortable and the house was very clean. Without question, we will stay here again when we return to Ironton. "
Charming Bungalow. Children and Pet Friendly.

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)

Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

10.0 out of 10, Exceptional, (24)
"Very clean, easy communication with host."
The price is SAR 526
SAR 924 total
includes taxes & fees
5 Jan - 6 January 2025
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

Historic Victorian close to amazing hiking - pet friendly!

9.0 out of 10, Wonderful, (2)
"Cute & clean home! Property manager was so easy to communicate with and super friendly!! We will be coming back!!"
Historic Victorian close to amazing hiking - pet friendly!

Rustic Ironton Home w/ Deck & Fire Pit on Creek!

9.8 out of 10, Exceptional, (56)
"Coming from Texas, we wanted to experience the changing leaves and the nature trails in the area but were pleasantly surprised when we found ourselves staying on a plot of civil war history. Our cabin was delightfully cozy, and the creek was a very nice place to sit near for our morning coffee. The views of the mountains from the front porch as the fog cleared were impeccable and we have already saved this spot in our list of places to visit again. "
Rustic Ironton Home w/ Deck & Fire Pit on Creek!

Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

9.4 out of 10, Exceptional, (10)
"We loved a lot of things about this house. The backyard is beautiful. We enjoyed the firepit and gazebo every night. We loved that the house is nice and spacious. There is enough room for everyone with 8 beds. Kids enjoyed the bunkbeds. The kitchen is nice and spacious and has a big countertop for cooking your own meals which we did all the days we were there. The location is Fantastic to Elephant Rocks State Park, Johnson Shut Ins and Taum Mountain State Park! The downfalls were the Asian...
The price is SAR 1,127
SAR 1,908 total
includes taxes & fees
25 Dec - 26 Dec
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Newly remodeled offers many amenities with perfect location!

10.0 out of 10, Exceptional, (24)
"The place was very clean and cute great location for visiting Elephant Rock, Johnson Shut in, Millstream gardens, many more things. House was as it shows the owners were very welcoming and informative. I would highly recommend the place it would sleep 6 very easy."
Newly remodeled offers many amenities with perfect location!

Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks

10.0 out of 10, Exceptional, (4)
"The house was great the yard was great wished we weren’t so rushed and had the time to enjoy the surroundings. The upstairs shower was on the small side, thin walls so depends on who you are sharing the upstairs with they will hear you and front bedroom you can hear the road very well. We had long days so able to sleep through it after the first night. This is a great country house. "
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks

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, (27)
"Great place overall! Internet and cell services lacking. "
Rustic Cabin in Hunters' Paradise!

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 SAR 365
SAR 722 total
includes taxes & fees
25 Dec - 26 Dec
Spring Street Cabin #2

Secluded Gate House

10.0 out of 10, Exceptional, (17)
"The property and place was wonderful!!"
Secluded Gate House

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

The Sutton House 2 blocks from Main Street & Courthouse Square

10.0 out of 10, Exceptional, (18)
"Great property, well stocked, very informative about the surrounding area. We enjoyed our stay! "
The price is SAR 654
SAR 834 total
includes taxes & fees
20 Jan - 21 January 2025
The Sutton House 2 blocks from Main Street & Courthouse Square

Charming 2-bedroom house in delightful Ellington with WiFi, AC, private big yard

2.0 star property
The price is SAR 451
SAR 729 total
includes taxes & fees
1 Jan - 2 January 2025
Charming 2-bedroom house in delightful Ellington with WiFi, AC, private big yard
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 #2 Annapolis, MO Black River

9.4 out of 10, Exceptional, (56)
"My husband and I came here with the hopes of escaping and just enjoying a peaceful weekend. The cabin is perfect for what we needed. Cozy and comfy and just what we needed. Yes the couch is broken, LOL. But if a broken couch is going to ruin your vacay maybe this isn’t the place for you. Just saying that just added to the character and provided some laughter. "
The price is SAR 446
SAR 814 total
includes taxes & fees
25 Dec - 26 Dec
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River

7.8 out of 10, Good, (26)
"Really a nice and clean and cozy stay."
The price is SAR 385
SAR 746 total
includes taxes & fees
25 Dec - 26 Dec
Hillside Cabin #3 Annapolis, MO Black River

Rustic River Cabin Getaway

9.6 out of 10, Exceptional, (70)
"We loved the cabin, it was clean and well kept. Google maps led us astray, but I called the owner and she got us right there. I loved the location, but wish it wasn’t such a long gravel road to get there. I’ll still go back anyway!"
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.