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Holiday Homes in Annapolis

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Annapolis holiday homes

Exterior

Secluded Log Cabin

Secluded Log Cabin
Annapolis
9.8 out of 10, Exceptional, (28 reviews)
"Stay was fine, nice peaceful setting, enjoyed our stay and would come back or recommend to others, thank you"
United States
Glen J.
The price is €189
includes taxes & fees
1 Jul - 2 Jul
Secluded Log Cabin
Interior

The Sutton House 2 blocks from Main Street & Courthouse Square

The Sutton House 2 blocks from Main Street & Courthouse Square
Ironton
10.0 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay. Nice big comfortable beds. Short walk to coffee shop & short drive to several nice hiking spots. "
United States
Nicole K.
The price is €267
includes taxes & fees
29 Jun - 30 Jun
The Sutton House 2 blocks from Main Street & Courthouse Square
Terrace/patio

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch

*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Ironton
10.0 out of 10, Exceptional, (37 reviews)
"Great place to stay!"
United States
Derek R.
The price is €247
includes taxes & fees
14 Jul - 15 Jul
*State Parks*Bungalow*CoffeeBar*Pet Friendly*Porch
Outdoor pool

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

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Park Hills
10.0 out of 10, Exceptional, (68 reviews)
"Very beautiful property! The Host was very responsive and courteous. 10/10 would stay here again and highly recommend it to others! "
United States
Mckayla M.
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Fridge, microwave, oven, stovetop

Charming 1860s Renovated Home

Charming 1860s Renovated Home
Ironton
8.0 out of 10, Very good, (19 reviews)
"Had a great stay"
United States
Kevin S.
The price is €290
includes taxes & fees
28 Jun - 29 Jun
Charming 1860s Renovated Home
Smart TV, books

AV Bungalows #4

AV Bungalows #4
Arcadia
10.0 out of 10, Exceptional, (4 reviews)
"Nice place to stay with all amenities plus pool, bbq area with bbqs and pickleball courts. Lots of sites to see in this area."
United States
Anthony B.
The price is €171
includes taxes & fees
26 Jul - 27 Jul
AV Bungalows #4
Dining

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

Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Lesterville
8.8 out of 10, Excellent, (18 reviews)
"Great house and location."
United States
Thomas M.
The price is €440
includes taxes & fees
29 Jun - 30 Jun
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Smart TV, books

Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa

Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa
Arcadia
10.0 out of 10, Exceptional, (1 review)
"The only issue we had was that the key was hard to insert and had to work at it to get the key all the way in and was worried it was going to break in the lock, I went to the hardware store and purchased graphite to help with the lock and now it works smoothly."
United States
Pamela B.
The price is €182
includes taxes & fees
1 Jul - 2 Jul
Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa
Exterior

AV Bungalows #2

AV Bungalows #2
Arcadia
The price is €211
includes taxes & fees
7 Jul - 8 Jul
AV Bungalows #2
1 bedroom, iron/ironing board, WiFi, bed sheets

AV Bungalows #9B

AV Bungalows #9B
Arcadia
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I really enjoyed our stay! The Bungalow was perfect for us and will definitely be staying again when we come back to Arcadia!!"
United States
Theresa R.
The price is €151
includes taxes & fees
29 Jun - 30 Jun
AV Bungalows #9B
Exterior

Arcadia Valley Bungalows #6 with heated Swim spa and outdoor pool

Arcadia Valley Bungalows #6 with heated Swim spa and outdoor pool
Arcadia
10.0 out of 10, Exceptional, (1 review)
"June 2024 and (sing it) "I'm hot. You're hot! He's hot! She's hot! WE'RE HOT! They're HOT! HOT HOT HOT!" Temp records are getting busted but we were happy and cool! Arcadia, MO isa less than half tank trip, including going to the Shut Ins during road construction and MAX A/C!!! We found fun people, good food, the bungalow was nice and cool and the ice maker was on! Neat and clean and you can tell these folks have been working hard. It was HOT when we arrived but the pool was cool and clean, even...
United States
Mary Lou S.
The price is €182
includes taxes & fees
28 Jun - 29 Jun
Arcadia Valley Bungalows #6 with heated Swim spa and outdoor pool
Living area

Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool

Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool
Arcadia
The price is €182
includes taxes & fees
8 Jul - 9 Jul
Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool
Living area

AV Bungalows #9A with Loft

AV Bungalows #9A with Loft
Arcadia
10.0 out of 10, Exceptional, (1 review)
"Amenities were great, house was perfect for our group, and easy access to local state parks."
United States
Allen D.
The price is €308
includes taxes & fees
29 Jun - 30 Jun
AV Bungalows #9A with Loft
Exterior

AV Bungalows #8

AV Bungalows #8
Arcadia
The price is €171
includes taxes & fees
8 Jul - 9 Jul
AV Bungalows #8
TV

AV Bungalows #1 with Loft

AV Bungalows #1 with Loft
Arcadia
8.0 out of 10, Very good, (1 review)
"The host was incredibly responsive and helpful. And for full transparency, we did not ask the host about this while we were there; however, the hot water in the showers was lukewarm at best. The hot water in the rest of the home was very warm. Also, the loft area was such a unique space. The kids loved it! Unfortunately, we were there when temperatures were in the single digits, so we needed to run the heat. ALL of it settled in the loft, leaving it much cooler everywhere else. The layout and...
United States
Tina T.
AV Bungalows #1 with Loft
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

Relaxing 3B Log Home-15 min walk to the Black River!

Relaxing 3B Log Home-15 min walk to the Black River!

10/10 Excellent
"This luxury cabin was the perfect getaway. For a remote location it has everything to keep a family busy happy and comfortable. The little details so well thought of from all the kitchen amenities to full closet of family games for the little and the older. Plenty of towels and blankets all clean . Initially we had trouble getting there ( use google maps not Waze ) the owner was fast to respond and help us out . Next door neighbours dog came morning and evening to great us … she is so friendly . All in all great stay recommend to all that happen to spend a weekend in the area ."
Tal 2-night trip
Posted 2 days ago
Relaxing 3B Log Home-15 min walk to the Black River!

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
221
Accommodation
34 Holiday Homes
Lowest Price
€151
Highest Price
€440