Holiday houses in Chester

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Top-rated holiday rentals in Chester

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Top Guest favourite
A spacious living area features exposed brick walls and original wood floors. Large windows provide natural light, while a comfortable sofa and dining table accommodate relaxation and meals. An area rug adds color, and modern lighting enhances the inviting atmosphere.
Loft in Perryville
4.97 out of 5 average rating, 330 reviews

Downtown Loft Amazing Bath Tub & Shower

Downtown Perryville, MO **DISCLAIMER** you will hear restaurant chatter & music if you do not have a tv/or radio playing between the hours of 10:30am & 1:30am. If you go to bed early I recommend headphones, ear plugs or play nature sounds on Alexa. This is a pet friendly loft apartment so I would not recommend if you are allergic to dogs or cats. This apartment is located above one of the most popular destination restaurant's around "Mary Jane Burgers & Brew" on the Downtown Historic Square.

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, 169 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 cabin with wooden exterior is surrounded by tall trees and shaded ground. A spacious porch is visible at the front entrance. A calm dog sits on the ground in the foreground, offering a glimpse of the natural tranquility of the setting.
Cabin in Alto Pass
4.99 out of 5 average rating, 316 reviews

Ma's Cabin, Alto Pass, IL. Fine country lodging.

Cute and country remodel done in 2019. Recent new appliances, furnishings, flooring, heat & A/C, washer & dryer. Cabin is secluded and quiet plus 1/2 mile from Alto Pass Lookout Point and right in the middle of many award-winning wineries. 15 miles from Carbondale 4 miles from Giant City 30 miles from Garden of the Gods 6 lakes within 10-mile radius Hundreds of miles of hiking trails in nearby Shawnee National Forest 6 miles from Bald Knob Cross Please, no dogs! No smoking in cabin!

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
4.95 out of 5 average rating, 198 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!

Top Guest favourite
A lakeside view showcases calm waters reflecting morning light. The home’s exterior features gray siding and white shutters. A grassy lawn is observed, bordered by a large tree. The scene captures the peaceful surroundings, inviting guests to experience the tranquil setting.
Home in Fredericktown
4.93 out of 5 average rating, 152 reviews

The GooseNest • HOT TUB • Lake View

Enjoy a comfortable stay at this unique lakeside retreat. This home offers two bedrooms and one bathroom. Start your day with coffee and a view of the lake. You’ll stay a short drive from several surrounding conservation sites. Bring your fishing pole and kayak! End your day relaxing by the fire pit and watching the sunset on the lake. We now offer event rentals for elopements, small wedding receptions, and small family reunions up to 18 people for an additional fee (message for details).

Top 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 home in Bloomsdale
4.93 out of 5 average rating, 236 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
A spacious porch is lined with wooden rocking chairs, offering a view of the surrounding greenery. An interior area features a cozy seating arrangement with a patterned rug and rustic decor. Outside, an inviting fire pit area with comfortable chairs is set amidst the natural landscape.
Cabin in Anna
4.9 out of 5 average rating, 163 reviews

Shawnee Hiking!Hot tub!Fire Pit!Wine Trail!

WELCOME TO LUXURY GLAMPING ON THE SHAWNEE WINE TRAIL OF BEAUTIFUL SOUTHERN ILLINOIS. You will be resting in an authentic oak timber cabin, built on the historical "Trail of Tears" in Union County - Anna, Illinois. This lodging offers the rustic appeal, a taste of Native America with the comforts of contemporary amenities including an outdoor hot tub all year long! *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #2.

Top Guest favourite
The treehouse structure is elevated, supported by stilts, with large windows that reflect the surrounding greenery. The exterior features a combination of wood finishes, and warm lighting casts a welcoming glow in the evening. The pathway leads through the natural landscape to the entrance.
Treehouse in Perryville
5 out of 5 average rating, 696 reviews

Private Treehouse Retreat | Hot tub

The TreeLoft is the first of two treehouses at BaseCamp—designed for cozy seclusion, romance, and rest. Nestled in a private forest just 1 hour from St. Louis, it blends upscale comfort with immersive nature, while still being 20–35 minutes from hiking, wineries, and dining. ✨Our NEW treehouse, The TreeRise, offers an even more elevated, spacious experience at BaseCamp. Perfect for romantic getaways, anniversaries, personal retreats, and intentional escapes to unplug and reconnect.

Top Guest favourite
Treehouse in Perryville
4.95 out of 5 average rating, 194 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.

Guest favourite
An outdoor fire pit area is surrounded by a grassy lawn, framed by lush greenery. Two red Adirondack chairs are positioned on a natural stone surface, offering a cozy spot to relax. The sky is bright with fluffy clouds, adding a serene ambiance to the scene.
Cabin in Fredericktown
4.98 out of 5 average rating, 103 reviews

Harmony Hills Cabin on The Little St Francis River

Rustic Cabin overlooking the Ozark Mountains. The Little St. Francis River is only a short walk from the scenic porch. Enjoy the serenity of nature or sit by the bonfire and enjoy a peaceful gaze at the stars. Cozy and well stocked, you'll find this place a home away from home. Bring your fishing poles, hiking boots, swim gear, kayak, a book or just kick back and relax. Please note, *** THERE IS NO WIFI or LIVE TV *** it isn't available in the area. We offer DVDs, books and games.

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, 403 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

Guest favourite
A covered porch offers expansive views of rolling hills and a glistening pond. A swing chair is positioned to the side, inviting relaxation, while flower beds with vibrant blooms border the entrance. Sunlight illuminates the landscape, enhancing the natural beauty of the surroundings.
Cabin in Fredericktown
4.97 out of 5 average rating, 334 reviews

Cabin on the farm

The Space Rustic charm meets the serene beauty of the Ozarks in this magical setting overlooking our farm, offering a perfect retreat for rest or a base camp for your next adventure. Inside, you'll find a cozy living space decorated with modern farmhouse charm, complete with a warm electric fireplace. Relax in the comfortable king-size bedroom after a day of exploring. The cottage also includes a well-appointed bathroom and a functional kitchenette for your convenience.

Popular amenities for Chester holiday rentals

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