Book Holiday Homes in Anna

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Featured Holiday Homes in Anna

Millers 2 lakehouse. Pontoon available to rent

Millers 2 lakehouse. Pontoon available to rent

Marion IL
When you a stay at this vacation home in Marion, you'll be on the waterfront, just steps from Shawnee National Forest and Lake of Egypt.
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Opens in a new windowMillers 2 lakehouse. Pontoon available to rent
On the Wine Trail - Minutes to Giant City, Shawnee Forest, SIU - Amazing Shower

On the Wine Trail - Minutes to Giant City, Shawnee Forest, SIU - Amazing Shower

Alto Pass IL
With a stay at this vacation home in Alto Pass, you'll be a 1-minute walk from Shawnee National Forest and 15 minutes by foot from Peachbarn Winery.
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Opens in a new windowOn the Wine Trail - Minutes to Giant City, Shawnee Forest, SIU - Amazing Shower
* On the Wine Trail * Hot Tub * Wi-Fi *

* On the Wine Trail * Hot Tub * Wi-Fi *

Alto Pass IL
A stay at this vacation home places you in the heart of Alto Pass, steps from Shawnee National Forest and 15 minutes by foot from Peachbarn Winery.
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Opens in a new window* On the Wine Trail * Hot Tub * Wi-Fi *
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Lake Front, Family fun- Sleeps 8, Newly modern remodeled 3bed/2bath private dock

Lake Front, Family fun- Sleeps 8, Newly modern remodeled 3bed/2bath private dock

Creal Springs IL
When you a stay at this vacation home in Creal Springs, you'll be on the waterfront, just steps from Shawnee National Forest and Lake of Egypt.
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Opens in a new windowLake Front, Family fun- Sleeps 8, Newly modern remodeled 3bed/2bath private dock
Charming 2-bedroom barn-style home nestled on 6 acres in delightful Vienna

Charming 2-bedroom barn-style home nestled on 6 acres in delightful Vienna

Vienna IL
The price is AU$253 per night from 5 Jan to 6 Jan
AU$253
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Vienna, this vacation home is within a 10-minute drive of Vienna City Park and Tunnel Hill State Trail.
Opens in a new windowCharming 2-bedroom barn-style home nestled on 6 acres in delightful Vienna
Relaxing lake front home with beautiful view on the lake, sleeps 7.

Relaxing lake front home with beautiful view on the lake, sleeps 7.

Creal Springs IL
With a stay at this vacation home in Creal Springs, you'll be just steps from Shawnee National Forest and Lake of Egypt.
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Opens in a new windowRelaxing lake front home with beautiful view on the lake, sleeps 7.
Notting Hill Cottage

Notting Hill Cottage

Alto Pass IL
Located in Alto Pass, this vacation home is a 1-minute drive from Shawnee National Forest and 6 minutes from Peachbarn Winery.
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Opens in a new windowNotting Hill Cottage
Sip, Hike, Relax - A Private 20-Acre Haven in Wine Country

Sip, Hike, Relax - A Private 20-Acre Haven in Wine Country

2 out of 5
Alto Pass IL
With a stay at this vacation home in Alto Pass, you'll be steps from Shawnee National Forest and a 3-minute drive from Peachbarn Winery.
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Opens in a new windowSip, Hike, Relax - A Private 20-Acre Haven in Wine Country
Newly Remodeled 3-BR in heart of Marion

Newly Remodeled 3-BR in heart of Marion

2 out of 5
Marion IL
Located in Marion, this vacation home is within a 5-minute drive of The Bark Park and Williamson County Historical Museum.
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Opens in a new windowNewly Remodeled 3-BR in heart of Marion
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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.

Anna 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 Anna vacation homes are the perfect way for you to wing it.

Holiday houses in Anna 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 Anna 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 Anna adventures, obvs.

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

Anna Holiday Homes essential information

Accommodation
186 Holiday Homes
Lowest Price
AU$142
Highest Price
AU$305
Popular accommodation
Millers 2 lakehouse. Pontoon available to rent, On the Wine Trail - Minutes to Giant City, Shawnee Forest, SIU - Amazing Shower, * On the Wine Trail * Hot Tub * Wi-Fi *, Lake Front, Family fun- Sleeps 8, Newly modern remodeled 3bed/2bath private dock, Charming 2-bedroom barn-style home nestled on 6 acres in delightful Vienna, Relaxing lake front home with beautiful view on the lake, sleeps 7. , Notting Hill Cottage, Sip, Hike, Relax - A Private 20-Acre Haven in Wine Country, Newly Remodeled 3-BR in heart of Marion

Top trending hotels in Anna

Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery

Brand new cabin in the woods with hot tub 1/2 mile from Starview Winery

Cobden IL
Located in Anna, this cabin is in a rural location, within a 5-minute drive of Shawnee National Forest and StarView Vineyards.
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Opens in a new windowBrand new cabin in the woods with hot tub 1/2 mile from Starview Winery
Hotel 7 Inn Anna

Hotel 7 Inn Anna

2.5 out of 5
100 Richview Dr Anna IL
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 28 Dec to 29 Dec
AU$142
28 Dec - 29 Dec
includes taxes & fees
Located in Anna, Hotel 7 Inn Anna is within a 5-minute drive of Shawnee Community College and Anna City Park.
Opens in a new windowHotel 7 Inn Anna
New cabin in the woods with private hot tub

New cabin in the woods with private hot tub

Cobden IL
Located in Anna, this cabin is in a rural location, within a 5-minute drive of Shawnee National Forest and StarView Vineyards.
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Opens in a new windowNew cabin in the woods with private hot tub
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Rest, Relax and Renew. Our log cabin experience awaits your arrival.

Rest, Relax and Renew. Our log cabin experience awaits your arrival.

Anna IL
The price is AU$305 per night from 28 Dec to 29 Dec
AU$305
28 Dec - 29 Dec
includes taxes & fees
Located in Anna, this cabin is on the waterfront, within a 10-minute drive of King Neptune Memorial and Dongola Public Library.
Opens in a new windowRest, Relax and Renew. Our log cabin experience awaits your arrival.
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See all available properties in Anna
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.