Vacation rentals in Simpson

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Top-rated vacation rentals in Simpson

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Top guest favorite
The cabin's welcoming entrance features a wooden porch supported by sturdy beams. Two rocking chairs sit on the porch, surrounded by greenery and stone accents. A red door and a large window enhance the cabin's rustic charm, while the natural setting invites relaxation.
Cabin in Cobden
4.99 out of 5 average rating, 168 reviews

Pop’s Country Cabin

Pop’s Country Cabin is a small remote cabin that sits 1/2mile off the road above a 5 acre lake on 77 acres of private land. The view from the front porch is amazing! You can sit, unwind, and watch the wildlife with a distant view of Bald Knob Cross. The cabin sits in the heart of Shawnee National Forrest and the Southern IL wine trail. You can enjoy the fire pit while watching the stars, with no distractions from neighbors, traffic, or lights. You can enjoy catch & release fishing from the bank

Top guest favorite
Home in Golconda
4.94 out of 5 average rating, 140 reviews

Dawns Retreat

No pets. Dawns Retreat is a farm house remodeled in 2023 with a rustic feel that offers a cozy relaxing stay. WiFi 3 smart tv’s 1 Queen 1 full Gas fireplace Gas grill Open fire grill Firewood Electricity at fire pit Plenty of parking Garage Deer hanging station. Heart of Shawnee National Forest. Golconda 10min. Eddyville 15min Harrisburg 35min Paducah KY 35min Note: the field around the yard is private property. Things to do in the area Horseback riding Hiking Boating Fishing Huntin

Top guest favorite
Cottage in Eddyville
4.94 out of 5 average rating, 186 reviews

Cozy one bedroom cottage on a horse farm

This special space is in the middle of the Shawnee National Forest, just a short drive to beautiful hiking, waterfalls, rock climbing, kayaking, and equestrian trails. -Guided horseback rides to Shawnee trails available through host, Sue -Corrals available for own horses -Sleeps 4-queen bed and pull out sofa -Washer and dryer -Fiber Optic WiFi -Gas grill, outdoor seating, large fire pit, and free firewood on site -Garden of the Gods, Jackson Falls, Bell Smith Springs Burden Falls nearby

Top guest favorite
A modern dome structure features large glass panels creating a bright and inviting environment. Surrounded by lush greenery, the architecture harmonizes with nature. A wooden deck with seating is visible in front, offering a space for relaxation and outdoor enjoyment.
Dome in Cobden
5 out of 5 average rating, 180 reviews

The Dome At Blueberry Hill

Escape to The Dome at Blueberry Hill, where comfort meets nature for a truly unforgettable glamping experience. Set on two private acres along the scenic Shawnee Hills Wine Trail and minutes from the charming village of Cobden- you’ll enjoy peaceful seclusion with easy access to local charm. The fully insulated dome offers cozy, climate-controlled comfort year-round. Sip wine under the stars or unwind in style indoors. Make lasting memories at The Dome- your luxury glamping retreat awaits.

Guest favorite
The exterior of a cozy wooden cabin is displayed, featuring a steeply pitched roof and large front windows. Two comfortable adirondack chairs are positioned nearby on a gravel path, alongside a small fire pit. Lush greenery surrounds the cabin, enhancing its serene setting.
Tiny home in Makanda
4.89 out of 5 average rating, 135 reviews

Tiny Cabin* Near Blue Sky*Shawnee*Pet Friendly

Après Vine Tiny Cabin is your escape to a serene minimalist cabin in Shawnee National Forest! Just 5 min to Blue Sky Vineyard, hiking, zip lines, and I-57, this retreat blends adventure and tranquility. Relax by the fire pit, take in sunsets, rolling pastures, and woodlands. No Wi-Fi or TV ensures a true digital detox. Friendly livestock guardian dogs may greet you. **Pet-Friendly when added to reservation! Perfect for nature lovers seeking a peaceful getaway or the minimalist adventurer!

Guest favorite
An A-frame cabin is displayed against a twilight sky, featuring a spacious deck adorned with string lights. The deck offers seating arrangements, inviting relaxation. The surrounding landscape includes a grassy area, contributing to the peaceful outdoor setting.
Cabin in Makanda
4.93 out of 5 average rating, 121 reviews

2BR A-Frame Cabin w/ Hot Tub Near Wine Trail

White Oak Cabin is the middle A-frame on a scenic property with three cabins, each with its own outdoor space. This cozy retreat features two queen beds, a hot tub, furnished kitchen (cooktop + convection microwave), Smart TV, WiFi, and a workspace. Enjoy a charcoal grill and access to a fully stocked pond. Just minutes from ziplining, Giant City State Park, the Shawnee Wine Trail, and nearby public land, it’s a great base for couples, friends, and small families exploring Southern Illinois.

Guest favorite
A bi-level home is set against a clear blue sky, surrounded by green lawn and blooming trees. A paved driveway leads to an attached garage, offering convenient access. The expansive landscape in the background hints at the property's spacious surroundings.
Home in Harrisburg
4.96 out of 5 average rating, 144 reviews

Spurlock Place- Shawnee National Forest (HOT TUB)

Hike, explore, work, or relax on our 2 country acres. Just 15 minutes from the Garden of the Gods, our home features a game room, high speed Internet, and plenty of space to spread out and enjoy nature. There’s a large gas station and DG store 1/2 mile away for anything you need, and Harrisburg is just a short drive further. If you’re looking to explore or hunt in the Shawnee National Forest, this is the perfect place to be! Guests have full access to the home, hot tub and all amenities.

Top guest favorite
A well-organized kitchen features wooden cabinetry and modern appliances, including a refrigerator and microwave. A window allows natural light, complemented by decorative valances. A patterned rug is placed near the sink, enhancing the functional space created by the open layout.
Tiny home in Ozark
4.96 out of 5 average rating, 541 reviews

The Potel Tiny Home 14x40

Tiny home nestled on the edge of the Shawnee National Forest. A cozy one bedroom with full closet and stacked washer and dryer the bed is a full size. Kitchen with stove, fridge and microwave. It does not have a dishwasher. Living room has a smart TV sign in to your Netflix, Sling, YouTube TV etc. Wi-fi provided. No cable. Full bathroom with shower unit. Some of our guest has said sitting on the porch watching the beautiful sunsets each night was an added bonus for staying with us.

Guest favorite
Condo in Paducah
4.96 out of 5 average rating, 694 reviews

Cozy studio in The Foxbriar - Downtown

Home of the former Foxbriar Inn, this condo is located inside a beautiful historic building. This space is great for your weekend away or a longer term stay. Exposed brick and high ceilings make it a charming and cozy experience. Enjoy the perks of walking to lots of great restaurants, specialty shopping and boutiques. We are just seconds from a beautiful stroll along the River. Bakery and coffee shop underneath. Enjoy brunch on the weekends or a sweet treat anytime in the week.

Top guest favorite
Dome in Stonefort
4.99 out of 5 average rating, 128 reviews

Modern Dome in Shawnee Forest with Hot Tub

Old Colorado Glamping Dome is nestled deep into the woods surrounded by beautiful tall pines. It is heated and cooled and has all the necessities as a typical house. We also packed as many amenities as we could into this property including an oversized 6-Person hot tub, 500 MBPS fiber internet, outdoor tv, fire pit table, Weber grill, hammock swings, custom bathroom with rainfall shower, full kitchen, coffee bar, king & queen sized beds, bean bag toss, board games and much more!

Guest favorite
A wooden deck lined with rustic rocking chairs offers a serene view of the surrounding forest. The lush greenery creates a peaceful backdrop, inviting relaxation and enjoyment of nature.
Cabin in Pope County
4.91 out of 5 average rating, 340 reviews

Beck's Hideaway at Dixon Springs

We might call this place a hideaway but the nearby activities and amenities are too numerous to list! Enjoy the secluded forest location surrounded by towering trees, abundant wildlife, and plenty of outdoor activities. Our cabin is just minutes away from the Trail of Tears, Dixon Springs State Park, the delicious Chocolate Factory, the towns of Golconda, Metropolis, and the bigger city of Paducah. NEW IN OCTOBER 2021: We have installed high-speed fiber optic WiFi to the cabin.

Guest favorite
A spacious patio is set with a dining table surrounded by chairs, complemented by a gas grill and umbrellas for shade. The cottage exterior features clean lines with multiple windows, while greenery and pine trees create a serene atmosphere.
Cottage in Vienna
4.96 out of 5 average rating, 163 reviews

Peaceful Cottage Retreat

Contactless Check-in. This cottage has everything you need for a relaxing getaway. It's private, tranquil setting is surrounded by nature. A queen bed with luxury bedding ensures a peaceful stay. The cottage comfortably accommodates 4 adults with the additional sleeper sofa. The kitchen includes a mini-fridge, microwave, toaster and coffeemaker. A cozy gas fireplace inside, and the large patio, gas grill, wood burning firepit, and a shady hammock compliment the outdoor space.

Popular amenities for Simpson vacation rentals

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