Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
Home in Ava
4.93 out of 5 average rating, 139 reviews

JGB’s Farm and Getaway

We are in the country next to a blacktop road.This is a very laidback place , there are farm animals across the road at our farm. This was my moms farm house and I just want people to enjoy it as much as she did. We are close to Kincaid Lake, the local winerie, the World Shooting Complex, and hiking trails (Piney Creek Revenue). Come and enjoy a day fishing or just sitting on the back deck enjoying the peaceful surroundings. Later build a fire and sit back and relax. Come and enjoy the country.

Top guest favourite
The geodesic dome is illuminated warmly from within, creating a welcoming glow against the night sky. The structure's unique shape and large window reveal a glimpse of the cozy interior, showcasing a serene space ideal for relaxation and connection with nature.
Dome in Perryville
4.94 out of 5 average rating, 173 reviews

The Snow Globe*OffGrid DomeGLAMP*Adventurers Only

EXPERIENCE The Dome in the Woods • IMMERSE in complete silence with the absence of electricity: no hum or vibrations from this completely solar/propane fueled geodesic dome. NoAC • GLAMP in this OFF GRID ADVENTURE. 430 sq ft floor plan. 14 ft ceiling. 20 ft bay window with endless nature view at the foot of your bed. Lofted 7ft. • STARGAZE from the deck or fire pit • NESTLE in the romantic wooded nature of southeast MO. S of St Louis.N of Memphis • UNPLUG, UNWIND, RELAX. Adventure seekers only!

Top guest favourite
A light-colored farmhouse is presented with a prominent stone chimney, featuring a welcoming front porch with wooden railings. Lush greenery, including a trimmed bush, enhances the entryway. Gravel leads up to the house, surrounded by open space and trees in the background.
Farm stay in Fredericktown
4.96 out of 5 average rating, 204 reviews

Spring Valley Ranch Rock House

This quaint farmhouse is located just off of MO Hwy 72 on a 62 acre farm nestled against the Castor River. Here you and your companion(s) can experience the quiet and relaxing life on a farm with plenty of adventure awaiting just around the bend. Sit and enjoy a sip of coffee or tea on the front porch while watching the cattle graze the pasture across the road next to a rustic white barn or venture about 3 miles to the largest privately owned lake in Madison County. Oh yes, enjoy your stay!

Guest favourite
The custom-built treehouse is elevated on stilts, surrounded by greenery. A spacious deck features a railing, offering access to the entrance. Steps lead to the ground below, while large glass doors enhance the connection to nature.
Treehouse in Cape Girardeau
5 out of 5 average rating, 208 reviews

Twisted Sassafras Treehouse

A custom-built treehouse located on 10 acres with a water view that you can take in from the hot tub on the deck! It is nestled high in the trees and is the perfect romantic getaway for two! Feel like you are away from it all without being away from it all! This treehouse is located on a county road just minutes from Cape Girardeau. Enjoy catch and release fishing on site, local wineries, shopping in historic downtown Cape Girardeau, local restaurants, gambling, historical sites & more!

Guest favourite
Home in Ellis Grove
5 out of 5 average rating, 12 reviews

Cozy Home In Southern Illinois

Welcome to your home away from home in the quiet, friendly town of Ellis Grove, Illinois! This 1 bedroom, 1 bath house is perfect for a peaceful getaway. The fully equipped kitchen has everything you need to cook, and the relaxing living space offers a warm, inviting place to unwind. Covered parking and laundry amenities included. You are just minutes from the scenic river views and prime hunting land. Whether you are here to relax, work, or explore the outdoors, this spot has you covered.

Guest favourite
The exterior of the tiny home is highlighted by a stone façade and a modern roof. A wooden deck features two classic Adirondack chairs, positioned against large glass doors that provide natural light and views of the surrounding grassy area.
Tiny homes in Bloomsdale
4.92 out of 5 average rating, 246 reviews

Coeur de la Crème Suite at Baetje Farms

Welcome to the Luxury Tiny Homes at Baetje Farms, where comfort meets countryside. These homes will awaken your senses and enlighten your soul with the cozy, yet spacious intimate feel beneath the stars. Nestled between rolling hills of the Forche du Clos Valley and a spring feed babbling creek the tiny homes are the newest addition to Baetje Farms. Just 3 miles off Interstate-55 at the entrance to wine country, in Bloomsdale, MO, Baetje Farms is the World Renowned Goat Cheese Creamery!

Top guest favourite
Two modern chairs are positioned in a corner, featuring a mix of yellow and black upholstery. Each chair includes a small foldable table, ideal for work or relaxation. Natural light filters through the windows, enhancing the inviting atmosphere of the space.
Apartment in Ste. Genevieve
4.95 out of 5 average rating, 79 reviews

“Be a part of the experience” at MUSIC ART HOME!

Located above the eclectic Music Art Love gallery/boutique/venue in the Little Bohemia area in downtown Ste. Genevieve you are welcomed to “be a part of the experience!” As a guest you receive discounts in the gallery, free admission to our events (Movie Nites, Open Mics, Concerts…), and a free bottle of wine! Centrally located to historic homes, unique shops, restaurants, antique mall, winery, & more! You’ll fall in love with our charming town! Enjoy your stay here at Music Art Home!

Top guest favourite
Treehouse in Perryville
4.95 out of 5 average rating, 202 reviews

Rustic reTREEt Treehouse Getaway

This treehouse features a gorgeous floor-to-ceiling stone indoor/outdoor fireplace, vaulted ceiling, and many large windows which provide natural light and beautiful views. The interior design fuses natural elements of wood and stone, with a more refined and polished urban country look. A partition wall creates intimate spaces w/in this large (950 sq.ft.) open floor plan. Highlights: king size bed, corner claw tub, rainfall shower, reading area, 65" TV, large deck,BBQ grill and WIFI.

Top guest favourite
The exterior of the cabin features a welcoming front porch with white railing and potted flowers. Large windows with shutters complement the gray siding, while a central arched window adds character. Lush greenery surrounds the cabin, enhancing its natural setting.
Cottage in Ava
4.95 out of 5 average rating, 121 reviews

Crazy Joe's Cabin #1

Located 2 miles off rt. 151 in Shawnee National forest. The cabin is along tree line just west of Crazy Joe’s Fish House. Restaurant is open at 4pm Wednesday, Friday and Saturday Guests receive $10 food voucher with stay 1bedroom cabin with queen bed, living room with queen sleeper sofa. Full kitchen, bathroom with shower,washer/dryer. Great place for hunting or fishing trip or get away. Smart tvs you can access apps We have 2 other rentals Crazy Joe’s Cabin 2 & Hickey House

Top guest favourite
The sleeping area features a queen-size bed with decorative pillows and a textured blanket. Soft lighting is provided by wall sconces, and a framed artwork enhances the wall above. A wooden bench rests at the foot of the bed, complementing the warm tones of the decor.
Guest suite in Perryville
4.96 out of 5 average rating, 407 reviews

Tranquil, Spacious Retreat to Rest and Relax!

This Private Guest Suite is nestled on the lower level of the home and offers a peaceful setting with great charm in which to rest and relax during your travels. ✦Features....... ✦Just 4 min from I-55 ✦Queen-Size Bed with Memory Foam topper ✦Sofa-bed for additional sleeping ✦Peaceful, Outdoor Sitting Area with Gas Firepit ✦55" Roku TV w/ surround sound ✦55" Roku TV in Bedroom & Electric Fireplace ✦Located at the end of a private lane - NO through traffic ✦NO Steps! ✦Home Gym

Top guest favourite
Home in Ste. Genevieve
5 out of 5 average rating, 15 reviews

Angel’s Hideaway • Last Shotgun House + Cozy + Lux

Stay at Angel’s Hideaway, the last original shotgun house in Ste. Genevieve—beautifully restored with warm cedar accents and elevated modern finishes. This boutique retreat features an electric fireplace, relaxing tub/shower, quartz kitchen, Heavenly Hair products, a charming front porch, and a serene back deck. The kitchen is fully stocked with premium essentials—because as travelers ourselves, we believe every stay should feel effortlessly luxurious. Love, Ashley & Jason

Top guest favourite
The historic log cabin features a traditional wood exterior, accented by a sloped roof and a welcoming front porch. Two rocking chairs and vibrant flower pots are positioned at the entrance, set against a tranquil landscape. Soft lighting enhances the inviting appearance as dusk approaches.
Cabin in Ste. Genevieve
4.97 out of 5 average rating, 228 reviews

Sassafras Creek Cabin

Historic log cabin circa 1840 moved to property June 2020. Take a step back in time with furniture and decor to match the cabin’s time period. Located between two houses in newly formed Ste. Genevieve National Historical Park. It is a 10 minute walk to the main part of downtown and other historic tour sites. Adjoins Early American gift shop called Sassafras Creek Originals which is housed in the circa 1850 Brooks house. Close to wineries, biking and hiking.

Popular amenities for Chester vacation rentals

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  2. United States
  3. Illinois
  4. Randolph County
  5. Chester