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Holiday Homes in Anna

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50 rentals in Anna.
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Rest, Relax and Renew or See Southern Illinois Like Never Before!, holiday rental in Anna

Rest, Relax and Renew or See Southern Illinois Like Never Before!

1 bedroom
1 bathroom
Sleeps 3
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Spacious 2 BR, 1 1/2 baths, hot tub, pool table, outside room, full kitchen, holiday rental in Anna

Spacious 2 BR, 1 1/2 baths, hot tub, pool table, outside room, full kitchen

2 bedrooms
2 bathrooms
Sleeps 6
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Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort, holiday rental in Anna

Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort

3 bedrooms
2 bathrooms
Sleeps 6
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AdamsRock Cabins mix Native American Charm with Luxury and Contemporary Comfort!, holiday rental in Anna

AdamsRock Cabins mix Native American Charm with Luxury and Contemporary Comfort!

2 bedrooms
2 bathrooms
Sleeps 6
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Come Sleep Where Abraham Lincoln Slept, holiday rental in Anna

Come Sleep Where Abraham Lincoln Slept

1 bedroom
1 bathroom
Sleeps 4
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Historical 'Kage House' Short Term Rental, holiday rental in Anna

Historical 'Kage House' Short Term Rental

1 bedroom
1 bathroom
Sleeps 3
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On the Shawnee Wine Trail, holiday rental in Anna

On the Shawnee Wine Trail

0 bedrooms
2 bathrooms
Sleeps 4
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Cabin near the Wine Trail, holiday rental in Anna

Cabin near the Wine Trail

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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How About Touring The Wineries This Spring? Stay at The Loft!, holiday rental in Anna

How About Touring The Wineries This Spring? Stay at The Loft!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Rental Cabin on Southern Illinois Wine Trail, Private Hot Tub, holiday rental in Anna

Secluded Rental Cabin on Southern Illinois Wine Trail, Private Hot Tub

2 bedrooms
1 bathroom
Sleeps 4
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Charming Cabin Overlooking 5 Acre Lake, holiday rental in Anna

Charming Cabin Overlooking 5 Acre Lake

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, holiday rental in Anna

Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful Cottage Retreat near Shawnee National Forest, holiday rental in Anna

Peaceful Cottage Retreat near Shawnee National Forest

1 bedroom
1 bathroom
Sleeps 4
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Serenity South -- Gardens, River-Views, and Refreshing Space, holiday rental in Anna

Serenity South -- Gardens, River-Views, and Refreshing Space

3 bedrooms
2 bathrooms
Sleeps 5
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Secluded, Log Rental Cabin, Private Hot Tub,on Southern Illinois Wine Trail, holiday rental in Anna

Secluded, Log Rental Cabin, Private Hot Tub,on Southern Illinois Wine Trail

2 bedrooms
2 bathrooms
Sleeps 6
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Easter in the Shawnee? Stay * The Barn, S.I.'s Largest Cabin on the Wine Trail!, holiday rental in Anna

Easter in the Shawnee? Stay * The Barn, S.I.'s Largest Cabin on the Wine Trail!

5 bedrooms
3 bathrooms
Sleeps 16
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Peaceful Red Roof Retreat - Nature and Night Sky, holiday rental in Anna

Peaceful Red Roof Retreat - Nature and Night Sky

1 bedroom
1 bathroom
Sleeps 6
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Southern Illinois Private Cottage, holiday rental in Anna

Southern Illinois Private Cottage

1 bedroom
1 bathroom
Sleeps 3
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Giant City State Park, Shawnee Wine Trail, Carbondale IL, Shawnee Nat'l Forest, holiday rental in Anna

Giant City State Park, Shawnee Wine Trail, Carbondale IL, Shawnee Nat'l Forest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Notting Hill Guest Cottage, holiday rental in Anna

Notting Hill Guest Cottage

2 bedrooms
1 bathroom
Sleeps 6
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Loft Apartment Across From Semo University Houch Field House. Walk  To Events, holiday rental in Anna

Loft Apartment Across From Semo University Houch Field House. Walk To Events

2 bedrooms
1 bathroom
Sleeps 5
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Breathtaking views and an absolute hiking paradise!!!, holiday rental in Anna

Breathtaking views and an absolute hiking paradise!!!

3 bedrooms
2 bathrooms
Sleeps 12
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Wine Trail Cabin - Carbondale, Southern Illinois - Giant City State Park, holiday rental in Anna

Wine Trail Cabin - Carbondale, Southern Illinois - Giant City State Park

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New, Unique Cave Creek Cabin 2, in Shawnee near Alto Pass and Bald Knob Cross, holiday rental in Anna

New, Unique Cave Creek Cabin 2, in Shawnee near Alto Pass and Bald Knob Cross

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Carbondale Pool House - Hot Tub, Sauna, Pet Friendly, holiday rental in Anna

Carbondale Pool House - Hot Tub, Sauna, Pet Friendly

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great Deal! Cave Creek Cabin #1in Alto Pass near Bald Knob and Shawnee Forest, holiday rental in Anna

Great Deal! Cave Creek Cabin #1in Alto Pass near Bald Knob and Shawnee Forest

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Downtown Getaway, holiday rental in Anna

Historic Downtown Getaway

1 bedroom
2 bathrooms
Sleeps 4
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Wine Country Cottage, holiday rental in Anna

Wine Country Cottage

2 bedrooms
2 bathrooms
Sleeps 6
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Wine Trail Log home, 6 mile views, beautiful sunset, close to SIU, Carbondale, holiday rental in Anna

Wine Trail Log home, 6 mile views, beautiful sunset, close to SIU, Carbondale

3 bedrooms
3 bathrooms
Sleeps 8
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Toolshed Corner Vacation Home, holiday rental in Anna

Toolshed Corner Vacation Home

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Large Brick Estate with pool in Quiet Neighborhood, holiday rental in Anna

Large Brick Estate with pool in Quiet Neighborhood

4 bedrooms
3 bathrooms
Sleeps 8
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New Jaybird Treehouse, holiday rental in Anna

New Jaybird Treehouse

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Cabin Retreat, holiday rental in Anna

Beautiful Cabin Retreat

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serenity North - Enclosed Gardens and Pet-Friendly Space, holiday rental in Anna

Serenity North - Enclosed Gardens and Pet-Friendly Space

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1920's Farm House Built by the Trainmaster of Carbondale. Modern updates in 2012, holiday rental in Anna

1920's Farm House Built by the Trainmaster of Carbondale. Modern updates in 2012

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Toolshed Corner House and Cabin, holiday rental in Anna

Toolshed Corner House and Cabin

5 bedrooms
4 bathrooms
Sleeps 16
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Quetil Trail Guesthouse, holiday rental in Anna

Quetil Trail Guesthouse

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Cottage at Eden (Downtown Cape Girardeau), holiday rental in Anna

The Cottage at Eden (Downtown Cape Girardeau)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Toolshed Corner Guest Cabin, holiday rental in Anna

Toolshed Corner Guest Cabin

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kerr Canyon Guest House - Wonderful Views, holiday rental in Anna

Kerr Canyon Guest House - Wonderful Views

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Betty's Vineyard House - Visit the Shawnee National Forest and Wine Trail!, holiday rental in Anna

Betty's Vineyard House - Visit the Shawnee National Forest and Wine Trail!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southern Illinois authentic 1905 cabin, holiday rental in Anna

Southern Illinois authentic 1905 cabin

3 bedrooms
1 bathroom
Sleeps 8
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Civil War home, close to downtown, holiday rental in Anna

Civil War home, close to downtown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Makanda Cabin in Shawnee National Forest, holiday rental in Anna

Beautiful Makanda Cabin in Shawnee National Forest

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Peaceful Custom Carbondale Home w/Pool Near SIU!, holiday rental in Anna

Peaceful Custom Carbondale Home w/Pool Near SIU!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Cottage at the Market, holiday rental in Anna

Cottage at the Market

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Carbondale Cottage w/ Fire Pit - 3 Mi to SIU!, holiday rental in Anna

NEW! Carbondale Cottage w/ Fire Pit - 3 Mi to SIU!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Directly on the Shawnee Hills Wine Trail,close to SIU,National Forest, FirePit, holiday rental in Anna

Directly on the Shawnee Hills Wine Trail,close to SIU,National Forest, FirePit

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Downtown Carbondale Cottage - 0.4 Mi to SIU!, holiday rental in Anna

NEW! Downtown Carbondale Cottage - 0.4 Mi to SIU!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Luxury Pine Cabin on 30 Wooded Acres, holiday rental in Anna

Luxury Pine Cabin on 30 Wooded Acres

1 bedroom
1 bathroom
Sleeps 4
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