Holiday Homes in Pinckneyville

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Featured Holiday Homes in Pinckneyville

Contemporary & Charismatic 5 Bedroom Home

10.0 out of 10, Exceptional, (25)
"Lovely home with plenty of room for 5 couples! Very clean. Close to town. Fit our needs perfectly."
Contemporary & Charismatic 5 Bedroom Home

Du Quoin Fairgrounds

10.0 out of 10, Exceptional, (2)
"Amazing house. Thank you for letting us stay at your place. "
The price is AU$281
includes taxes & fees
1 Dec - 2 Dec
Du Quoin Fairgrounds

Stylish 3 BR house. Downtown Carbondale with fenced in yard.

9.4 out of 10, Exceptional, (24)
"We have stayed here many times. It is the perfect location for our SIU visits. We will be back!"
Stylish 3 BR house. Downtown Carbondale with fenced in yard.

Hilltop Retreat 2: Spacious, pond-front home for 12 near wine trail!

9.8 out of 10, Exceptional, (21)
"We absolutely loved the property. It sits right on a pond that my two sons fished on everyday. They caught bass crappie and blue gill. The house was very spacious and clean. I was shocked to not see ANY bugs since it is in a wooded area. Major plus!!! The kitchen had everything we needed. The host very responsive when we needed her. The lakes were about 15 min away, shopping was about 25 min away. There are plenty of wineries and hikes. I do recommend going to giant city and eating at the lodge...
Hilltop Retreat 2: Spacious, pond-front home for 12 near wine trail!

Upscale Designer Studio Across from SIUC Campus

10.0 out of 10, Exceptional, (15)
"Small but cute! I would stay again and recommend!"
The price is AU$258
includes taxes & fees
1 Dec - 2 Dec
Upscale Designer Studio Across from SIUC Campus

Farmstead home w/hot tub

9.8 out of 10, Exceptional, (8)
"Excellent stay! Clean, great location for World Shooting Complex and close to Sparta. Highly Recommend 🌟 "
The price is AU$445
includes taxes & fees
1 Dec - 2 Dec
Farmstead home w/hot tub

Country getaway on 5 acres. Five minutes from Fairgrounds. Clean and new!

9.6 out of 10, Exceptional, (4)
"We were in town for a family wedding. The location was perfect, the property was more than what we had hoped for. Communication with the host was great. We will definitely considering staying again. "
Country getaway on 5 acres. Five minutes from Fairgrounds. Clean and new!

Charming 2-bedroom house with WiFi and AC in quaint Sesser near Rend Lake

10.0 out of 10, Exceptional, (1)
"The house was great very clean . "
The price is AU$305
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom house with WiFi and AC in quaint Sesser near Rend Lake

Brick Estate with pool in Quiet Carbondale Neighborhood

9.4 out of 10, Exceptional, (81)
"This house was perfect for three (or four) couples. The kitchen was extremely well stocked and the house was beautifully decorated. Unfortunately the pool was already closed and it rained the whole weekend. But we still had a great time playing games and watching football. The neighborhood is very quiet. I would definitely recommend this property and look forward to visiting again. "
Brick Estate with pool in Quiet Carbondale Neighborhood

Country Home for the Family

10.0 out of 10, Exceptional, (30)
"We loved having room indoors to gather and outdoors to play."
Country Home for the Family

Southern Charm in the Heart of the Midwest!

10.0 out of 10, Exceptional, (9)
"We are a group of ladies who have been friends for many years and have stayed many places. We loved it!!! "
Southern Charm in the Heart of the Midwest!

Beautiful Views from Every Direction

10.0 out of 10, Exceptional, (35)
"This property is beautiful. The area is peaceful and the house is just as listed. Lots of special touches, charging ports in each bedroom, TV in each bedroom and lots more. They say the little things matter. Five stars "
Beautiful Views from Every Direction

On the Lake & Wine Trail & a Perfect Getaway for16 + With an ADA Suite!

10.0 out of 10, Exceptional, (13)
"We so enjoyed this home for our family reunion!! Family from Georgia, California, Ohio and Oregon stayed in the home. We had our reunion at the home on Saturday. Other family from near hear in Illinois gathered from around. We had almost 50 family from 2-year-olds through 88-year-olds! Got to celebrate my only living uncle's birthday! The wrap around porch was perfect all day long. Weather was good all weekend for us. When the sun got a little too hot we just kept moving around the porch to find...
On the Lake & Wine Trail & a Perfect Getaway for16 + With an ADA Suite!

One of Our Newest Properties That Has Quickly Become a Guest Favorite!

10.0 out of 10, Exceptional, (11)
"Possibly one of the best vrbos my family has stayed in. Kitchen is fully equipped and we cooked every night. The bedrooms offer comfy beds and linens with plenty of privacy. The outdoor area is great…nice grill, firepit, and hot tub. "
One of Our Newest Properties That Has Quickly Become a Guest Favorite!

Upscale, Luxurious Home with Lake View and Fountains!

10.0 out of 10, Exceptional, (28)
"Very relaxing and enjoyable. SUPER clean!"
Upscale, Luxurious Home with Lake View and Fountains!

Cozy home with the right amenities for your visit to our sweet town.

10.0 out of 10, Exceptional, (10)
"My sister and I loved this little home. Cozy and comfortable, it was very clean. The hostess supplied extra towels and even snacks. We highly recommend this home to visitors to Nashville. 🌻👍"
The price is AU$237
includes taxes & fees
3 Dec - 4 Dec
Cozy home with the right amenities for your visit to our sweet town.

Shady Lakes Escape-w/n minutes from Wineries & Lakes!

10.0 out of 10, Exceptional, (6)
"It was so clean and peaceful! It was perfect for our family of 10.. "
Shady Lakes Escape-w/n minutes from Wineries & Lakes!

Peaceful Country Home

10.0 out of 10, Exceptional, (41)
"My family had a weekend trip to the area for a wedding. This was our second time staying. We enjoy the little pond and porch swing. Having easy access to kitchen and open concept living room is great for kids."
The price is AU$406
includes taxes & fees
10 Dec - 11 Dec
Peaceful Country Home

Creekside Valley: secluded, spacious home for 8!

9.6 out of 10, Exceptional, (17)
"The property was nice. We had no issues at all. The property manager was very accommodating and communicated with us promptly. Definitely a great place to stay if you like the feeling of being at a clubhouse. The cabin itself was nice. It could use a few updates. The front porch and back deck was a little rough looking, but the inside was nice and clean. The one bedroom is huge. You could fit a few full size air-mattresses on there along with the bed, and the bathroom attached is also huge....
Creekside Valley: secluded, spacious home for 8!

°4Bdrmsw/EnSuites*Plus1/2bath°

9.8 out of 10, Exceptional, (12)
"We had an amazing time at the house, the host was very thoughtful about everything they had in the house! Perfect getaway! "
°4Bdrmsw/EnSuites*Plus1/2bath°
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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Other property types in Pinckneyville

Lake & Oaks Hideaway- Hidden Cabin on Private Lake

10.0 out of 10, Exceptional, (28)
"The lot was great. We couldn't ask for a better spot of land to visit. It was a quite area with beautiful views all the way around. The inside could use a bit of care. We expected rustic and that's one of the places charms. There were many positives such as a ping-pong table, plenty of sleeping space, and lots of television options. Opportunities included the bathroom and other areas could use a serious look. We didn't shower (we were only there overnight) due to the shower conditions. Grout...
The price is AU$378
includes taxes & fees
26 Dec - 27 Dec
Lake & Oaks Hideaway- Hidden Cabin on Private Lake

The Old Water Dept! | Next to SIUC

10.0 out of 10, Exceptional, (14)
"LOVE the proximity to SIUC and my student’s apartment. Property is always clean. The ambiance is relaxing and modern."
The price is AU$258
includes taxes & fees
1 Dec - 2 Dec
The Old Water Dept! | Next to SIUC

Experience Glamping in style. Private Hot tub spa! Private lake -Pet Friendly

10.0 out of 10, Exceptional, (14)
"Nice little place close to several things to do "
The price is AU$269
includes taxes & fees
1 Dec - 2 Dec
Experience Glamping in style. Private Hot tub spa! Private lake -Pet Friendly
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.