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Compare 26 Vacation Homes in Annapolis with updated reviews, rates, and availability.

The Sutton House 2 blocks from Main Street & Courthouse Square

10.0 out of 10, Exceptional, (22)
"Beautiful stately home in peaceful neighborhood close to Elephant Rock and Johnston Shut Ins. Highly recommended! "
The price is SAR 503
SAR 653 total
includes taxes & fees
16 Apr - 17 Apr
The Sutton House 2 blocks from Main Street & Courthouse Square

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

10.0 out of 10, Exceptional, (28)
"Our family of 4 stayed two nights so we could hike Elephant Rocks and Johnson's Shut-Ins. Cute little house, with everything we needed for a pleasant stay. Had warm weather and really enjoyed the Adirondack chairs on the front porch for morning coffee. We did discovered that being in town in March, Tuesday-Thursday, meant many businesses were not open. Checo's Mexican, Arcadia Valley Coffee, and the The Iron Mule were all delightful, and we are food/coffee snobs from Chicago :-)"
The price is SAR 492
SAR 886 total
includes taxes & fees
16 Apr - 17 Apr
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

10.0 out of 10, Exceptional, (59)
"Nice farmhouse in the country."
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Historic Victorian close to amazing hiking - pet friendly!

8.8 out of 10, Excellent, (6)
"Comfortable"
Historic Victorian close to amazing hiking - pet friendly!

Newly remodeled offers many amenities with perfect location!

10.0 out of 10, Exceptional, (26)
"Our family had such a great time at the olde homestead and we especially appreciated all of the extras like the Rec room in the garage, the fire pit, and the animals at the property. Our hosts treated us like the first guest they ever had, even after several years of hosting. The house was adorable and the proximity to the state parks was perfect! They have thought of everything and made us feel right at home!"
Newly remodeled offers many amenities with perfect location!

Charming 1860s Renovated Home

8.0 out of 10, Very Good, (16)
"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 1,010 total
includes taxes & fees
16 Apr - 17 Apr
Charming 1860s Renovated Home

Charming Country Bungalow - perfect for families

10.0 out of 10, Exceptional, (13)
"Our family wanted somewhere to stay close to Elephant Rocks and this little house was perfect! Great area upstairs for our young kids to play and overall a comfortable home. Thank you for sharing it with us!!"
Charming Country Bungalow - perfect for families

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

10.0 out of 10, Exceptional, (5)
"House was perfect for our girls weekend in Caledonia. Kitchen stocked with all the necessities! Snack tray was so sweet of Stacy to leave out for us. The decor is so thoughtful. We loved the Easter decorations throughout the house. Outside seating was comfortable. Porch swing was enjoyable. We loved our stay. We are a group of 63-73 years olds not in the best shape however we managed the steps to upstairs bedroom. Slow slow steady. "
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks

Secluded Gate House

10.0 out of 10, Exceptional, (19)
"The gatehouse was amazing. We loved the hiking trails, the grounds, and the location. Campfires were super easy by the lounge. We loved being super close to so much great hiking! We would stay here again in a heartbeat."
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)

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 1,126
SAR 1,888 total
includes taxes & fees
11 May - 12 May
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

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

10.0 out of 10, Exceptional, (13)
"Perfect for our needs. Plenty of room and great place to ride out of. House had everything we needed. Owner was quick to respond with any questions. Would go back 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!

Just Minutes from Black River – With WIFI

6.0 out of 10, (4)
"So many issues... 1) Does not have a finished ceiling as shown in pics. Metal roof was exposed to the inside, rusted, and had holes. 2) 6' radius water stain in corner of LR carpet. BR carpets were badly stained, as well. 3) Cabinetry old and signs of mice in drawers. Signs of mice in BRs and bath also. 4) Fixed arm faucet installed on double basin sink so water hit divider and had to be twisted to avoid splashing exposing holes where hot/cold water lines were supposed to be. So, cold water...
The price is SAR 365
SAR 721 total
includes taxes & fees
16 Apr - 17 Apr
Just Minutes from Black River – With WIFI

Serene Belgrade Hideaway with Fire Pit & Grill!

9.6 out of 10, Exceptional, (4)
"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!

Vacation home conveniently located near Clearwater Lake and Black River

10.0 out of 10, Exceptional, (1)
"This home is so cute and we loved it as soon as we walked in. It feels much larger than it is and is very comfortable. There are little touches everywhere that make you feel at home, from the nicely stocked little coffee bar, to the throw blankets by the couch, to the full kitchen, to the washer/dryer combo . . . It was exactly what we needed! Located on a little country road, it was very quiet and peaceful yet close to town if we needed anything (we didn't!) The owner was quickly available...
The price is SAR 657
SAR 786 total
includes taxes & fees
16 Apr - 17 Apr
Vacation home conveniently located near Clearwater Lake and Black River

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

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

Cabin near Clearwater Lake

Cabin near Clearwater Lake

Park Model TinyHome with spacious front porch table outdoor furniture and spa.

Park Model TinyHome with spacious front porch table outdoor furniture and spa.
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

Make your reservation fast as inquiries are coming in daily.

9.8 out of 10, Exceptional, (52)
"Pictures on line do not do the cabin justice. It is way nicer in person. View to the river is incredible. We highly recommend renting. I know we will be back. Jeff is a great host who provides any and all information you request. Last minute perfect getaway for Thanksgiving!"
Make your reservation fast as inquiries are coming in daily.

New Cabin Just Minutes from Black River

7.4 out of 10, Good, (3)
"Owner communicated well and the place was a nice clean place for us to stay "
The price is SAR 486
SAR 944 total
includes taxes & fees
16 Apr - 17 Apr
New Cabin Just Minutes from 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.