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Vacation Homes in Annapolis

Our top choices for Annapolis vacation homes

The Sutton House 2 blocks from Main Street & Courthouse Square

10.0 out of 10, Exceptional, (34)
"Great property, well stocked, very informative about the surrounding area. We enjoyed our stay! "
The price is AED 512
AED 663 total
includes taxes & fees
3 Sep - 4 Sep
The Sutton House 2 blocks from Main Street & Courthouse Square

Charming Country Bungalow - perfect for families

10.0 out of 10, Exceptional, (20)
"We really enjoyed our stay here. It has a large fenced yard, which was perfect for my dogs to be able to go out and run around and play. You can sit outside around a fire in the evening. The home is very cute and clean. Walking distance to a Mexican restaurant and coffee shop. Another few local restaurants in close driving distance. Go to Back Porch Pub and Grill, sit outside and chat with the owner, Dan. Short drive to state parks for hiking and sightseeing. Johnson’s Shut Ins was definitely...
Charming Country Bungalow - perfect for families

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

10.0 out of 10, Exceptional, (15)
"Always live to stay here when we head down that way for a sxs trip. "
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Just Minutes from Black River – With WIFI

6.8 out of 10, (5)
"Plenty of privacy and everything you need. The owner was great at communicating."
The price is AED 357
AED 699 total
includes taxes & fees
3 Sep - 4 Sep
Just Minutes from Black River – With WIFI

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)

Newly remodeled offers many amenities with perfect location!

10.0 out of 10, Exceptional, (31)
"We enjoyed the property very much. It was nice and cozy and conveniently located close to Elephant Rocks and Johnson Shut Ins. If we come back to the area, we would definitely stay at this property again. We were in town for a family girls trip and it suited us well."
Newly remodeled offers many amenities with perfect location!

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

10.0 out of 10, Exceptional, (66)
"A very nicely accommodated property set in a peaceful area. Pool was a life saver for us with the weather temps. Very much enjoyed the stay."
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

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

9.2 out of 10, Wonderful, (17)
"The house was perfect for what we needed. Close to the river yet also gave us our privacy. Great patio and fire pit area. I would definitely stay there again."
The price is AED 1,102
AED 1,848 total
includes taxes & fees
3 Sep - 4 Sep
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Rustic Cabin in Hunters' Paradise!

9.8 out of 10, Exceptional, (29)
"We enjoyed our stay and will be back!"
Rustic Cabin in Hunters' Paradise!

Charming 1860s Renovated Home

8.0 out of 10, Very Good, (17)
"Had a great stay"
The price is AED 496
AED 988 total
includes taxes & fees
4 Sep - 5 Sep
Charming 1860s Renovated Home

Spacious & Secluded Shook Home w/ Private Hot Tub!

9.4 out of 10, Exceptional, (3)
"Very comfortable beds and pillows and the cookies the host left were delicious "
Spacious & Secluded Shook Home w/ Private Hot Tub!

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

10.0 out of 10, Exceptional, (30)
"Very friendly, helpful host, clean and cute house. Love the area for shops, and hiking we had a wonderful stay!"
The price is AED 503
AED 893 total
includes taxes & fees
3 Sep - 4 Sep
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

Clearwater Lake and Black River Vacation Home

9.6 out of 10, Exceptional, (18)
"Nice clean property! Comfortable beds plenty of seating. "
Clearwater Lake and Black River Vacation Home

Secluded Gate House

10.0 out of 10, Exceptional, (24)
"Our pups and us had a lovely stay at this beautiful, peaceful, well maintained property. Communication with the host was prompt and check in and out was a breeze! "
Secluded Gate House

Secluded Log Cabin

9.8 out of 10, Exceptional, (23)
"Beds were comfortable, outdoor area was wonderful, not far from town. Enjoyed our stay very much."
Secluded Log Cabin

Cabin near Clearwater Lake

Cabin near Clearwater Lake

Walk to Dtwn: Ironton Home in Historic District

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay at this home. Not only is it close to several state parks and sights, but Lynn also let me know about some of the local happenings in town that were fun to check out as well. Any time I had a question, Lynn got right back to me and made us feel at home. She even provided dog bowls and a kennel to help us with our dogs. Great stay and great owner!"
Walk to Dtwn: Ironton Home in Historic District

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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Top Annapolis Hotel Reviews