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Anna Vacation Rentals

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

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

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort, vacation rental in Anna
Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort, vacation rental in Anna
Our 2nd Luxury Cabin shares Native American Charm & Contemporary Comfort, vacation rental in Anna

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious 2 BR, 1 1/2 baths, hot tub, pool table, outside room, full kitchen

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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AdamsRock Cabins mix Native American Charm with Luxury and Contemporary Comfort!, vacation rental in Anna
AdamsRock Cabins mix Native American Charm with Luxury and Contemporary Comfort!, vacation rental in Anna
AdamsRock Cabins mix Native American Charm with Luxury and Contemporary Comfort!, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Come Sleep Where Abraham Lincoln Slept, vacation rental in Anna
Come Sleep Where Abraham Lincoln Slept, vacation rental in Anna
Come Sleep Where Abraham Lincoln Slept, vacation rental in Anna

Come Sleep Where Abraham Lincoln Slept

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Rental Cabin on Southern Illinois Wine Trail, Private Hot Tub, vacation rental in Anna
Secluded Rental Cabin on Southern Illinois Wine Trail, Private Hot Tub, vacation rental in Anna
Secluded Rental Cabin on Southern Illinois Wine Trail, Private Hot Tub, vacation rental in Anna

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cabin in Southern Illinois - Hot Tub - Romantic Getaway -Shawnee National Forest, vacation rental in Anna
Cabin in Southern Illinois - Hot Tub - Romantic Getaway -Shawnee National Forest, vacation rental in Anna
Cabin in Southern Illinois - Hot Tub - Romantic Getaway -Shawnee National Forest, vacation rental in Anna

Cabin in Southern Illinois - Hot Tub - Romantic Getaway -Shawnee National Forest

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Jetted Tubs - 4th Night Free* - Wi-Fi - Wonderful Views, vacation rental in Anna
Jetted Tubs - 4th Night Free* - Wi-Fi - Wonderful Views, vacation rental in Anna
Jetted Tubs - 4th Night Free* - Wi-Fi - Wonderful Views, vacation rental in Anna

Jetted Tubs - 4th Night Free* - Wi-Fi - Wonderful Views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW!  Wine Country Farmhouse ON THE WINE TRAIL! Perfect Location! Your own lake!, vacation rental in Anna
NEW!  Wine Country Farmhouse ON THE WINE TRAIL! Perfect Location! Your own lake!, vacation rental in Anna
NEW!  Wine Country Farmhouse ON THE WINE TRAIL! Perfect Location! Your own lake!, vacation rental in Anna

NEW! Wine Country Farmhouse ON THE WINE TRAIL! Perfect Location! Your own lake!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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On the Shawnee Wine Trail

Rental Home
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk to Wineries - Quaint Village - Grill - Patio - WiFi - Amazing Shower, vacation rental in Anna
Walk to Wineries - Quaint Village - Grill - Patio - WiFi - Amazing Shower, vacation rental in Anna
Walk to Wineries - Quaint Village - Grill - Patio - WiFi - Amazing Shower, vacation rental in Anna

Walk to Wineries - Quaint Village - Grill - Patio - WiFi - Amazing Shower

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Makanda Cabin w/Deck in Shawnee National Forest!, vacation rental in Anna
Makanda Cabin w/Deck in Shawnee National Forest!, vacation rental in Anna
Makanda Cabin w/Deck in Shawnee National Forest!, vacation rental in Anna

Makanda Cabin w/Deck in Shawnee National Forest!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cabin near the Wine Trail, vacation rental in Anna
Cabin near the Wine Trail, vacation rental in Anna
Cabin near the Wine Trail, vacation rental in Anna

Cabin near the Wine Trail

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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⭐⭐⭐⭐⭐ Big Sky Cabin! Fire Pit! Pool Table! 2 Decks!Jacuzzi Tub! Wifi! Private!, vacation rental in Anna
⭐⭐⭐⭐⭐ Big Sky Cabin! Fire Pit! Pool Table! 2 Decks!Jacuzzi Tub! Wifi! Private!, vacation rental in Anna
⭐⭐⭐⭐⭐ Big Sky Cabin! Fire Pit! Pool Table! 2 Decks!Jacuzzi Tub! Wifi! Private!, vacation rental in Anna

⭐⭐⭐⭐⭐ Big Sky Cabin! Fire Pit! Pool Table! 2 Decks!Jacuzzi Tub! Wifi! Private!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 20
Match: Sleeps
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Cozy Cottage On The Shawnee Hills Wine Trail, vacation rental in Anna
Cozy Cottage On The Shawnee Hills Wine Trail, vacation rental in Anna
Cozy Cottage On The Shawnee Hills Wine Trail, vacation rental in Anna

Cozy Cottage On The Shawnee Hills Wine Trail

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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4th night Free*  - Wonderful Views - Daily Deer Viewing - Quiet and Private, vacation rental in Anna
4th night Free*  - Wonderful Views - Daily Deer Viewing - Quiet and Private, vacation rental in Anna
4th night Free*  - Wonderful Views - Daily Deer Viewing - Quiet and Private, vacation rental in Anna

4th night Free* - Wonderful Views - Daily Deer Viewing - Quiet and Private

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Charming Cabin Overlooking 5 Acre Lake, vacation rental in Anna
Charming Cabin Overlooking 5 Acre Lake, vacation rental in Anna
Charming Cabin Overlooking 5 Acre Lake, vacation rental in Anna

Charming Cabin Overlooking 5 Acre Lake

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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How About Touring The Wineries This Spring? Stay at The Loft!, vacation rental in Anna
How About Touring The Wineries This Spring? Stay at The Loft!, vacation rental in Anna
How About Touring The Wineries This Spring? Stay at The Loft!, vacation rental in Anna

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, vacation rental in Anna
Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, vacation rental in Anna
Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Betty's Vineyard House - On the Shawnee Wine Trail, vacation rental in Anna
Betty's Vineyard House - On the Shawnee Wine Trail, vacation rental in Anna
Betty's Vineyard House - On the Shawnee Wine Trail, vacation rental in Anna

Betty's Vineyard House - On the Shawnee Wine Trail

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Feels like your in a Tree House! On the Creek! Fire Pit! 2min to the Winery!, vacation rental in Anna
Feels like your in a Tree House! On the Creek! Fire Pit! 2min to the Winery!, vacation rental in Anna
Feels like your in a Tree House! On the Creek! Fire Pit! 2min to the Winery!, vacation rental in Anna

Feels like your in a Tree House! On the Creek! Fire Pit! 2min to the Winery!

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded, Log Rental Cabin, Private Hot Tub,on Southern Illinois Wine Trail, vacation rental in Anna
Secluded, Log Rental Cabin, Private Hot Tub,on Southern Illinois Wine Trail, vacation rental in Anna
Secluded, Log Rental Cabin, Private Hot Tub,on Southern Illinois Wine Trail, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Wi-Fi - 4th Night Free - On Shawnee Hills Wine Trail - Near Giant City St. Park, vacation rental in Anna
Wi-Fi - 4th Night Free - On Shawnee Hills Wine Trail - Near Giant City St. Park, vacation rental in Anna
Wi-Fi - 4th Night Free - On Shawnee Hills Wine Trail - Near Giant City St. Park, vacation rental in Anna

Wi-Fi - 4th Night Free - On Shawnee Hills Wine Trail - Near Giant City St. Park

Rental Home
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Southern Illinois Private Cottage, vacation rental in Anna
Southern Illinois Private Cottage, vacation rental in Anna
Southern Illinois Private Cottage, vacation rental in Anna

Southern Illinois Private Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Giant City State Park, Shawnee Wine Trail, Carbondale IL, Shawnee Nat'l Forest, vacation rental in Anna
Giant City State Park, Shawnee Wine Trail, Carbondale IL, Shawnee Nat'l Forest, vacation rental in Anna
Giant City State Park, Shawnee Wine Trail, Carbondale IL, Shawnee Nat'l Forest, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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New Wine Trail Carriage House, Cozy, Clean, Hiking, Biking, Shawnee Nat'l Forest, vacation rental in Anna
New Wine Trail Carriage House, Cozy, Clean, Hiking, Biking, Shawnee Nat'l Forest, vacation rental in Anna
New Wine Trail Carriage House, Cozy, Clean, Hiking, Biking, Shawnee Nat'l Forest, vacation rental in Anna

New Wine Trail Carriage House, Cozy, Clean, Hiking, Biking, Shawnee Nat'l Forest

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Home, Modern & Charming Decor, Wine Trail, Private Rental, vacation rental in Anna
Historic Home, Modern & Charming Decor, Wine Trail, Private Rental, vacation rental in Anna
Historic Home, Modern & Charming Decor, Wine Trail, Private Rental, vacation rental in Anna

Historic Home, Modern & Charming Decor, Wine Trail, Private Rental

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Easter in the Shawnee? Stay * The Barn, S.I.'s Largest Cabin on the Wine Trail!, vacation rental in Anna
Easter in the Shawnee? Stay * The Barn, S.I.'s Largest Cabin on the Wine Trail!, vacation rental in Anna
Easter in the Shawnee? Stay * The Barn, S.I.'s Largest Cabin on the Wine Trail!, vacation rental in Anna

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Notting Hill Guest Cottage, vacation rental in Anna
Notting Hill Guest Cottage, vacation rental in Anna
Notting Hill Guest Cottage, vacation rental in Anna

Notting Hill Guest Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Breathtaking views and an absolute hiking paradise!!!, vacation rental in Anna
Breathtaking views and an absolute hiking paradise!!!, vacation rental in Anna
Breathtaking views and an absolute hiking paradise!!!, vacation rental in Anna

Breathtaking views and an absolute hiking paradise!!!

Rental Home
3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, vacation rental in Anna
Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, vacation rental in Anna
Wine Trail Cabin, 2015 Built, Carbondale, Southern IL - Giant City State Park, vacation rental in Anna

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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New, Unique Cave Creek Cabin 2, in Shawnee near Alto Pass and Bald Knob Cross, vacation rental in Anna
New, Unique Cave Creek Cabin 2, in Shawnee near Alto Pass and Bald Knob Cross, vacation rental in Anna
New, Unique Cave Creek Cabin 2, in Shawnee near Alto Pass and Bald Knob Cross, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wine Trail Cabin - Carbondale, Southern Illinois - Giant City State Park, vacation rental in Anna
Wine Trail Cabin - Carbondale, Southern Illinois - Giant City State Park, vacation rental in Anna
Wine Trail Cabin - Carbondale, Southern Illinois - Giant City State Park, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Amazing View,  on Wine trail , close  to SIU, Lakes and Giant City, vacation rental in Anna
Amazing View,  on Wine trail , close  to SIU, Lakes and Giant City, vacation rental in Anna
Amazing View,  on Wine trail , close  to SIU, Lakes and Giant City, vacation rental in Anna

Amazing View, on Wine trail , close to SIU, Lakes and Giant City

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pine Cabin on 30 Acres! 1 mi. from Carbondale, IL & SIUC Campus, vacation rental in Anna
Pine Cabin on 30 Acres! 1 mi. from Carbondale, IL & SIUC Campus, vacation rental in Anna
Pine Cabin on 30 Acres! 1 mi. from Carbondale, IL & SIUC Campus, vacation rental in Anna

Pine Cabin on 30 Acres! 1 mi. from Carbondale, IL & SIUC Campus

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Peaceful Custom Carbondale Home w/Pool Near SIU!, vacation rental in Anna
Peaceful Custom Carbondale Home w/Pool Near SIU!, vacation rental in Anna
Peaceful Custom Carbondale Home w/Pool Near SIU!, vacation rental in Anna

Peaceful Custom Carbondale Home w/Pool Near SIU!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Great Deal! Cave Creek Cabin #1in Alto Pass near Bald Knob and Shawnee Forest, vacation rental in Anna
Great Deal! Cave Creek Cabin #1in Alto Pass near Bald Knob and Shawnee Forest, vacation rental in Anna
Great Deal! Cave Creek Cabin #1in Alto Pass near Bald Knob and Shawnee Forest, vacation rental in Anna

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wi-Fi - Jetted Tubs - On the Wine Trail - 2 Houses, 1 Property, vacation rental in Anna
Wi-Fi - Jetted Tubs - On the Wine Trail - 2 Houses, 1 Property, vacation rental in Anna
Wi-Fi - Jetted Tubs - On the Wine Trail - 2 Houses, 1 Property, vacation rental in Anna

Wi-Fi - Jetted Tubs - On the Wine Trail - 2 Houses, 1 Property

Rental Home
5 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Wine Country Cottage, vacation rental in Anna
Wine Country Cottage, vacation rental in Anna
Wine Country Cottage, vacation rental in Anna

Wine Country Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wine Trail Log home, 6 mile views, beautiful sunset, close to SIU, Carbondale, vacation rental in Anna
Wine Trail Log home, 6 mile views, beautiful sunset, close to SIU, Carbondale, vacation rental in Anna
Wine Trail Log home, 6 mile views, beautiful sunset, close to SIU, Carbondale, vacation rental in Anna

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stay directly on the Wine Trail, vacation rental in Anna
Stay directly on the Wine Trail, vacation rental in Anna
Stay directly on the Wine Trail, vacation rental in Anna

Stay directly on the Wine Trail

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Toolshed Corner Vacation Home, vacation rental in Anna
Toolshed Corner Vacation Home, vacation rental in Anna
Toolshed Corner Vacation Home, vacation rental in Anna

Toolshed Corner Vacation Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Cabin Retreat, vacation rental in Anna
Beautiful Cabin Retreat, vacation rental in Anna
Beautiful Cabin Retreat, vacation rental in Anna

Beautiful Cabin Retreat

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Carbondale Cottage w/ Fire Pit - 3 Mi to SIU!, vacation rental in Anna
NEW! Carbondale Cottage w/ Fire Pit - 3 Mi to SIU!, vacation rental in Anna
NEW! Carbondale Cottage w/ Fire Pit - 3 Mi to SIU!, vacation rental in Anna

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Toolshed Corner Guest Cabin, vacation rental in Anna
Toolshed Corner Guest Cabin, vacation rental in Anna
Toolshed Corner Guest Cabin, vacation rental in Anna

Toolshed Corner Guest Cabin

Cabin
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Toolshed Corner House and Cabin, vacation rental in Anna
Toolshed Corner House and Cabin, vacation rental in Anna
Toolshed Corner House and Cabin, vacation rental in Anna

Toolshed Corner House and Cabin

Cabin
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Quetil Trail Guesthouse, vacation rental in Anna
Quetil Trail Guesthouse, vacation rental in Anna
Quetil Trail Guesthouse, vacation rental in Anna

Quetil Trail Guesthouse

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Kerr Canyon Guest House - Wonderful Views, vacation rental in Anna
Kerr Canyon Guest House - Wonderful Views, vacation rental in Anna
Kerr Canyon Guest House - Wonderful Views, vacation rental in Anna

Kerr Canyon Guest House - Wonderful Views

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Directly on the Shawnee Hills Wine Trail,close to SIU,National Forest, FirePit, vacation rental in Anna
Directly on the Shawnee Hills Wine Trail,close to SIU,National Forest, FirePit, vacation rental in Anna
Directly on the Shawnee Hills Wine Trail,close to SIU,National Forest, FirePit, vacation rental in Anna

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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