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Compare 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, (7)
"My daughter-in-law and I stayed here on our overnight hiking trip. The house was perfectly clean and well-stocked. We both slept well and had a wonderful time. We especially appreciated not having to do anything before checking out… just locked the door behind us! We both said we’d stay here again!"
The price is AED 639
AED 827 total
includes taxes & fees
24 Jun - 25 Jun
The Sutton House 2 blocks from Main Street & Courthouse Square
AV Bungalows #7
10.0 out of 10, Exceptional, (1)
"We stayed one night. They are still working on amenties which are nice. The neighborhood is quiet."
The price is AED 575
AED 623 total
includes taxes & fees
23 Jun - 24 Jun
AV Bungalows #7
Newly remodeled offers many amenities with perfect location!
10.0 out of 10, Exceptional, (14)
"I went there with 3 of my lifelong friends to ride Harley Davidsons through the Arcadia Valley. The Olde Homestead is a beautifully remodeled property in a great location. The house is clean & newly furnished with 3 nice bedrooms (king & 2 fulls) and 2 full bathrooms, living room, etc. 2 decks/patio and a garage let you spend time outside regardless of the weather. The area is great for sightseeing, and it was great for motorcycle riding and the property is perfectly located for both....
Newly remodeled offers many amenities with perfect location!
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Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
10.0 out of 10, Exceptional, (53)
"We traveled here for a week long stay. We had 6 adults and one child. The property was just as listed and everyone enjoyed the pool and hot tub. We made most our meals and the kitchen was stocked appropriately. Linda was an excellent host and responded very quickly to our questions/concerns."
The price is AED 1,502
AED 2,567 total
includes taxes & fees
10 Jul - 11 Jul
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, (48)
"Having the creek running near the house was awesome for us. Beds were very comfortable and we felt like we were at home. "
Rustic Ironton Home w/ Deck & Fire Pit on Creek!
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 AED 1,102
AED 1,859 total
includes taxes & fees
23 Jun - 24 Jun
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, (5)
"Had an amazing stay, with a fun day at Jeff’s canoe rental!! Place was clean and great for family, friends!"
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
Charming Bungalow. Children and Pet Friendly.
10.0 out of 10, Exceptional, (6)
"The property was beautiful from top to bottom, inside and out. Anna has done great work in this and keeps your stay feeling lighthearted anytime you are in the house. I had a couple special requests to help celebrate a birthday and she pulled through and helped out perfectly. We will definitely be coming back again."
Charming Bungalow. Children and Pet Friendly.
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 AED 436
AED 785 total
includes taxes & fees
23 Jun - 24 Jun
Spring Street Cabin #2
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
10.0 out of 10, Exceptional, (15)
"The house was clean and comfortable. Directions and amenities were as described. Close to state parks for ease. Owners were helpful and accommodating."
The price is AED 466
AED 896 total
includes taxes & fees
23 Jun - 24 Jun
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins
Enjoy a charming 1860s newly renovated home!!
8.0 out of 10, Very Good, (6)
"I celebrated my birthday with a float trip over the weekend - all of us adults. It was perfect for the weekend, and very homey!"
The price is AED 575
AED 1,075 total
includes taxes & fees
23 Jun - 24 Jun
Enjoy a charming 1860s newly renovated home!!
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks
10.0 out of 10, Exceptional, (2)
"This home was beautiful. So close to the sweet downtown. Plenty of room. Lovely place to visit."
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, (1)
"While we were in the middle of nowhere, it was still great. We kind of expect middle of no where when we visit family in Wappapello! The house was absolutely adorable and they had everything there for us! We booked it for Christmas, and the day after it was booked the owner called to ask if we wanted a Christmas tree and decorations. I was stunned and absolutely thrilled. We definitely weren’t expecting to have decorations but it was wonderful! We definitely want to go back on our next visit!"
Spacious & Secluded Shook Home w/ Private Hot Tub!
Rustic Cabin in Hunters' Paradise!
9.8 out of 10, Exceptional, (23)
"Property was in decent order and repair, although there were no trash bags or toilet paper. Inside the home was a little dirty but overall fairly clean. Internet is EXTEREMELY slow, mostly unusable."
Rustic Cabin in Hunters' Paradise!
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
Secluded Gate House
10.0 out of 10, Exceptional, (12)
"This property is perfect for anyone that desires a secluded getaway. The grounds are vast with amazing views and trails for the nature lover. The owner, Linda, is wonderful and responds quickly to texts. The dining table had a tray of snacks and candy that was enjoyed after long hikes. Also had K-cups for that much needed quick cup of Joe. I thoroughly enjoyed my stay with my beloved golden doodle, he also gives The Loft of Arcadia 5 woofs!!!"
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)
Historic 1856 Eversole Home Decorated with Period Furniture & Quilts
10.0 out of 10, Exceptional, (1)
"Overall I'm impressed with the upkeep of this historic property. It was well kept and situated right in the middle of town providing us convenient walking access to the venue. Definitely would recommend staying if you're in the area!"
Historic 1856 Eversole Home Decorated with Period Furniture & Quilts
Clearwater Lake and Black River Vacation Home
9.6 out of 10, Exceptional, (16)
"The house is nice and cozy and clean. The furniture is very comfortable. The kitchen is well stocked with cooking utensil and pans. LOTS of towels and toilet paper! The owners are very nice and accommodating. Ice and firewood are available for inexpensive cash purchase on property. Very easy access to the lake and marina. The only challenge was the WiFi. It worked ok for some streaming services, but less so for anything else. We had a lot of fun. Hope to see you again soon!"
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!
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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.

Other property types in Annapolis

Rustic River Cabin Getaway
9.6 out of 10, Exceptional, (60)
"Wonderful place to stay while kayaking the Black River. Clean, well stocked, super communication from the host. If you are looking for a very quiet cabin and the serenity of the woods, look no further."
Rustic River Cabin Getaway
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 AED 555
AED 1,011 total
includes taxes & fees
11 Jul - 12 Jul
Hillside Cabin #4 Annapolis, MO Black River
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 AED 436
AED 785 total
includes taxes & fees
23 Jun - 24 Jun
Hillside Cabin #3 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.

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