Book Holiday Homes in Annapolis

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Featured Holiday Homes in Annapolis

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
Book a stay at this family-friendly vacation home in Park Hills. Enjoy free WiFi, private pools, and a water park. Popular attractions St. Joe State Park and ...
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

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

Redford
Stay at this vacation home in Reynolds County. Enjoy patios, in-room jetted tubs, and an in-room coffeemaker. Popular attraction K Bridge Recreation Area is ...
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge
Sunshine Shack at Clearwater Lake (sleeps 6)

Sunshine Shack at Clearwater Lake (sleeps 6)

Piedmont
Book a stay at this family-friendly vacation home in Piedmont. Enjoy free WiFi, a garden, and patios. Popular attraction Clearwater Lake is located nearby.
Sunshine Shack at Clearwater Lake (sleeps 6)
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Historic Victorian close to amazing hiking - pet friendly!

Historic Victorian close to amazing hiking - pet friendly!

Fredericktown
The price is NZ$242 per night from 29 Jan to 30 Jan
NZ$242
includes taxes & fees
29 Jan - 30 Jan
Stay at this vacation home in Fredericktown. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attraction Madison County Courthouse is located ...
Historic Victorian close to amazing hiking - pet friendly!
Rustic Ironton Home w/ Deck & Fire Pit on Creek!

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

Ironton
Stay at this vacation home in Ironton. Enjoy furnished lanais, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Arcadia Valley Golf ...
Rustic Ironton Home w/ Deck & Fire Pit on Creek!
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
The price is NZ$895 per night from 24 Jan to 25 Jan
NZ$895
includes taxes & fees
24 Jan - 25 Jan
Stay at this vacation home in Lesterville. Enjoy air conditioning and a spa tub. Popular attraction Taum Sauk Nature Museum is located nearby.
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.
Newly remodeled offers many amenities with perfect location!

Newly remodeled offers many amenities with perfect location!

Ironton
Stay at this vacation home in Ironton. Enjoy a garden, tennis courts, and patios. Popular attractions Fort Davidson State Historic Site and Battle of Pilot Knob ...
Newly remodeled offers many amenities with perfect location!
Enjoy a charming 1860s newly renovated home!!

Enjoy a charming 1860s newly renovated home!!

Ironton
The price is NZ$475 per night from 24 Jan to 25 Jan
NZ$475
includes taxes & fees
24 Jan - 25 Jan
Stay at this vacation home in Ironton. Enjoy free WiFi and air conditioning. Popular attractions Shepherd Mountain Bike Park and Hiking Trails and Arcadia Valley ...
Enjoy a charming 1860s newly renovated home!!
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks

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

Caledonia
Book a stay at this family-friendly vacation home in Caledonia. Enjoy free WiFi, a garden, and patios. Popular attraction Big River is located nearby.
Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks
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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.

Annapolis Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Annapolis vacation homes are the perfect way for you to wing it.

Holiday houses in Annapolis let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Annapolis in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Annapolis adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Annapolis with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Annapolis vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Annapolis Holiday Homes essential information

Accommodation
23 Holiday Homes
Lowest Price
NZ$242
Highest Price
NZ$895
Popular accommodation
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE, Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge, Sunshine Shack at Clearwater Lake (sleeps 6), Historic Victorian close to amazing hiking - pet friendly!, Rustic Ironton Home w/ Deck & Fire Pit on Creek!, Gorgeous large rental home in Lesterville MO just minutes from Blackwater River., Newly remodeled offers many amenities with perfect location!, Enjoy a charming 1860s newly renovated home!!, Family getaway beautiful wraparound porch sleeps 13+ near hiking and state parks

Top trending hotels in Annapolis

Hillside Cabin #3   Annapolis, MO  Black River

Hillside Cabin #3 Annapolis, MO Black River

Annapolis
The price is NZ$349 per night from 6 Feb to 7 Feb
NZ$349
includes taxes & fees
6 Feb - 7 Feb
Stay at this cabin in Annapolis. Enjoy free WiFi, a garden, and balconies. Popular attractions Walnut Hollow Lake and K Bridge Recreation Area are located ...
Hillside Cabin #3 Annapolis, MO Black River
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

Annapolis
The price is NZ$378 per night from 24 Jan to 25 Jan
NZ$378
includes taxes & fees
24 Jan - 25 Jan
Stay at this cabin in Annapolis. Enjoy balconies, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Walnut Hollow Lake and K Bridge ...
Hillside Cabin #2 Annapolis, MO Black River
Rustic River Cabin Getaway

Rustic River Cabin Getaway

Annapolis
Stay at this cabin in Annapolis. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Walnut Hollow Lake and K Bridge Recreation ...
Rustic River Cabin Getaway
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Hillside Cabin #4 Annapolis, MO Black River

Hillside Cabin #4 Annapolis, MO Black River

Annapolis
The price is NZ$488 per night from 24 Jan to 25 Jan
NZ$488
includes taxes & fees
24 Jan - 25 Jan
Stay at this cabin in Annapolis. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Walnut Hollow Lake and K Bridge ...
Hillside Cabin #4 Annapolis, MO Black River
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See all available properties in Annapolis
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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.

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^Subject to availability and chosen travel dates.