Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

A single-story home is set on a green lawn, featuring a light brown exterior and a neatly maintained pathway leading to the front door. Windows with red and white accents provide a welcoming touch, while trees line the background, offering a sense of privacy.

Home in Bloomsdale

4.9 out of 5 average rating, 221 reviews

Hop off the highway, Relax!

Relax with the whole family at this peaceful place to stay. We are located only 4 miles off of highway 55! There are two bedrooms and two COMFY couches if you have more than 4 staying the night! This is located on a secluded road with two other homes occupied nearby by with quite, but very friendly, residents. This home is 25 minutes away from the historical town of Ste Genevieve, take a look! The host is will be able to assist you almost immediately, whether it be over the app or in person!

Top guest favorite

A charming farmhouse with a green metal roof stands amidst lush greenery. The front porch features a wooden railing and is adorned with flowering plants. Large windows allow natural light to fill the interior, while trees provide a serene backdrop.

Home in Ava

4.93 out of 5 average rating, 122 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.

Guest favorite

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, 322 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 favorite

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

4.95 out of 5 average rating, 148 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 favorite

The exterior of a charming cottage features a welcoming entrance with a light-colored door. Two blue chairs and a small table are positioned on a stone path, surrounded by well-maintained grass and flower pots. In the background, horses can be seen grazing in a fenced pasture.

Guesthouse in Carbondale

5 out of 5 average rating, 250 reviews

Homestead Cottage

Enjoy tiny farmhouse life in this adorable 375 sq. foot cottage. Loaded with everything you need this little cottage is nestled privately behind some trees on our 11 acre farm. You will soon forget how close you are to town with the beautiful view from your windows and the pasture fence just steps out the back door. Whether you’re here for the wineries, amazing hiking, an SIU event (3 miles) or to visit with family, the Homestead Cottage will provide a comfortable retreat from any adventure.

Top guest favorite

A charming street scene captures the historic architecture of Ste. Genevieve. Colorful storefronts line the sidewalk, featuring a gallery and residences, while seasonal flowers add vibrancy. Trees with remaining leaves provide a natural canopy over the pavement, leading to parked vehicles in the distance.

Home in Ste. Genevieve

4.95 out of 5 average rating, 177 reviews

"Little Brick House" (Hael House built in 1865)

Best downtown location!! Take a trip back in time at this cozy, centrally-located brick cottage in historic Ste. Genevieve. The original home of John and Francesca Hael in the 1860's, you won't find a more authentic old town experience than you will get at "the little brick house" on Main Street. Enjoy mornings at the local coffee shops and bakeries (right across the street) and evenings on the back porch with a glass of wine. The Little Brick House has all the amenities with old world charm!

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, 103 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.

Top guest favorite

A modern kitchen features a spacious granite countertop and light cabinetry. Natural light from a nearby window brightens the space. An inset view displays a vibrant arcade area with several vintage arcade games, creating a playful contrast to the kitchen's sleek design.

Home in Ste. Genevieve

4.97 out of 5 average rating, 173 reviews

Downtown home + Arcade 1980's experience!

If you’re looking for a unique experience to enjoy with your friends and family you have found the right place! Peaceful and centrally-located place with a front porch view of the Gabouri creek and train trestle. Downtown shops and restaurants within walking distance. 1 King, 1 Queen, 1 Full bed. 1 bath with shower + 1 bath with tub. Arcade with 11 vintage games, pinball, and Shooting Gallery! Most games set to free play! *some take coin* *No parties - access limited to guest only*

Top guest favorite

The charming exterior of a light blue house is framed by lush greenery. A welcoming porch adorned with decorative flags, potted plants, and a sign greets visitors. The well-maintained lawn features manicured bushes, enhancing the inviting atmosphere of this peaceful setting.

Bungalow in Ste. Genevieve

4.98 out of 5 average rating, 133 reviews

Dove’s Nest: Serenity & Comfort Sleeps 6

Check in at 3pm. Check out 11am Code upon arrival High speed AT&T 18MBS Family friendly, couples, girls trip. Owners of the Cozy Haven tiny house rental Airbnb. next door. And Wrens Landing found on Airbnb to rent Downtown. Shops, wineries, restaurants,bars. People travel all over to experience town and french culture. Oldest settlement west Mississippi river. Coffee bar and teas. 65 inch smart tv. Each bedroom has Roku smart tv. Outside firepit & dining area. No pets.

Top guest favorite

Treehouse in Perryville

5 out of 5 average rating, 656 reviews

Couples Retreat in the Trees + Hot tub

The TreeLoft is a custom built luxury treehouse for two nestled in the eastern part of the Ozark Mountains. Enjoy the gas fireplace for a cozy evening ambiance, a private hot tub under the stars, roasting s'mores over an evening fire or an early morning soak in the free standing tub. All of this is located within 20-45 minute scenic drive of hiking trails, wineries, and restaurants . It is our hope that upon your stay you will be reconnected to nature and to the one you came with.

Top guest favorite

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

4.94 out of 5 average rating, 108 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

Guest favorite

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, 382 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