Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

A private hot tub is surrounded by illuminated palm plants, creating a serene atmosphere at night. Soft blue lights reflect off the water, and a lantern adds a warm glow, enhancing the peaceful retreat.

Tiny home in Park Hills

4.96 out of 5 average rating, 649 reviews

🔝❤️ PEACEFUL TREETOP COTTAGE

KrystaRating, 5 stars1 week ago

Such a beautiful place and couple. Impeccable hosting. We felt very taken care of. We came for a staycation for my fiancés’ birthday and were warmly welcomed and taken care of. Thank you for the amazing stay! We look forward to coming back.

Top guest favorite

A hot tub is illuminated with soft blue lighting, surrounded by a wooden deck. String lights hang above, creating a gentle glow in the evening. A grill is positioned nearby on the patio, enhancing the outdoor relaxation space.

Home in Cobden

4.93 out of 5 average rating, 61 reviews

Wine trail, views, hot tub, pool…

PhyllisRating, 5 stars3 days ago

What a beautiful home in an excellent location. Loved the layout. Plenty of room to visit with friends. The large deck was wonderful and the view is amazing. The beds were very comfy and the master bedroom downstairs is perfect. The decor is beautiful yet very comfortable. Our host Lisa is very responsive and always available to help if needed. This home is a rare find and we will definitely return. Thank you Lisa for sharing your home with us.

Top guest favorite

A wooden deck features a round table surrounded by four metal chairs, set against a backdrop of trees. The quiet outdoor space offers ample room for relaxation, with a parasol positioned at the table, allowing for comfortable shade.

Cabin in Alto Pass

4.99 out of 5 average rating, 272 reviews

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

JosephRating, 5 stars1 week ago

THANK YOU AGAIN SO MUCH! We had a fantastic weekend. Ma's Cabin was the perfect "home-base" for our hiking adventures. Was so peaceful to relax after hiking all the trails. Everything we needed for our getaway. Sid and Patty were so friendly and of course Lillie stole the show ❤️. Thank you again!

Guest favorite

Home in Bonne Terre

4.8 out of 5 average rating, 54 reviews

PEACEFUl home w/ Trails, Rolling hills & Lakeside

RonaldRating, 5 stars1 month ago

The house and property are beautiful and very private. The back porch was a great location to watch the sunsets. Also, kitchen now a microwave which was a bonus since previous comments talked about no microwave. Our phones connected to 5G so the fact that there was no a TV or wifi wasn't an issue for us. The beds were comfortable and everything was clean. The house is about 30-40 minutes (or less) from 3-4 state parks. Would definitely stay again!

Superhost

An open living area features wooden beams and a spiral staircase leading to a loft. Colorful armchairs are positioned beside a small table, with natural light filtered through sheer pink curtains. A vibrant area rug adds texture to the wood floor.

Cottage in Ste. Genevieve

4.74 out of 5 average rating, 168 reviews

Ruby’s Rental

KellyRating, 5 stars1 month ago

This place is so charming and so cute. It's private and cozy, but also just a mile from all the sights, restaurants , boutiques in Ste Genevieve. We loved the hot tub and the back porch where we could sit and relax. Kitchen was well-appointed - we did a lot of cooking.

Top guest favorite

A rustic wooden container holds a variety of snacks, including popcorn, crackers, cookie packs, and cheese snacks. The container is divided into sections to neatly organize the items, and the surrounding area features wood paneling and a textured countertop.

Home in Sesser

4.95 out of 5 average rating, 129 reviews

Hunting, fishing, golf & beaches!

TeresaRating, 5 stars2 weeks ago

I booked this house for family that was visiting from out of state. Check in was extremely smooth. The only snag was the key pad didn't function on the last night (battery died) but Penny was right there to take care of things. Staying here was much better than a hotel room as it gave them space to spread out.

Top guest favorite

A new hot tub sits within a screened porch, surrounded by views of trees. Gentle water bubbles are visible, creating a relaxing atmosphere ideal for unwinding and enjoying the natural setting.

Cabin in Carbondale

4.97 out of 5 average rating, 151 reviews

Couple's Retreat with HOT TUB

ChristenRating, 5 stars1 week ago

Another great stay on the property. We love the location and proximity to everything. Also, the property is accomodating for our fishing boat. Tom-tom (the cat) was a fantastic little amenity at the cabin. He greeted us upon our return and joined us for our morning coffee. Give him all the love!

Top guest favorite

Home in Farmington

4.97 out of 5 average rating, 38 reviews

Come experience relaxation at Eva’s Retreat LLC.

EvaRating, 5 stars3 days ago

We came in for our 50th class reuion . Eva's Retreat was awesome. Loved the gameroom. Everything was so nice and clean. Had Everything we needed. Jonathon was excellent to work with. The back yard is so big and beautiful . Will definitely be staying here again.

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Popular amenities for Chester vacation rentals

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Other great vacation rentals in Chester

Guest favorite

The outdoor patio features a black metal table and chairs, surrounded by potted colorful plants. Natural light fills the area, showcasing a serene view of the water and the lush green landscape beyond. The rustic cottage design adds charm to this relaxing outdoor space.

Cabin in Bonne Terre

4.96 out of 5 average rating, 649 reviews

The Waterfront cottage

DawnRating, 5 stars1 week ago

Perfect little getaway spot! Cabin was super cute with unique features. We loved being able to fish right off the back deck and the paddle boat was also a fun extra. The property is picture perfect and peaceful. Hosts were also wonderful and very responsive, thank you!

Guest favorite

A well-equipped kitchen features light wooden cabinetry and granite countertops. Stainless steel appliances, including a refrigerator and microwave, enhance functionality. Natural light enters through a window, complementing the tiled flooring and a small plant placed on the countertop.

Home in Carterville

4.93 out of 5 average rating, 45 reviews

Experience Carterville Charm near Southern IL Univ

DeniseRating, 5 stars2 months ago

We enjoyed our stay here. The house was exactly as described and in a quiet neighborhood. The house was also very clean, from the bedrooms and living room to the kitchen, which had all of the utensils, pot and pans you'd need for cooking. We also unexpectedly needed to stay an extra night and Lori quickly responded and made it happen seamlessly for us.

Guest favorite

A cozy living space is presented with comfortable seating, including a brown sofa and an accent chair. Natural light floods through large windows, highlighting a sleeping area with a spacious bed in the background. A ceiling fan adds functionality to the inviting atmosphere.

Home in Carbondale

5 out of 5 average rating, 14 reviews

Owls Nest

GustaboRating, 5 stars1 month ago

The Owls Nest was a perfect place to stay with our family and our 2 dogs. The fenced in back yard had plenty of room, a fire pit and nice sized deck. The bedrooms were all cozy and had comfortable beds. The living room has plenty of room to play games or watch a movie and the kitchen has everything you need . We love to hike and Mt Bike and this location was close to many hiking trails and about a 5 min drive to Touch of Nature trails for riding. We would definitely book another stay at the Owls Nest!

Superhost

An aerial view captures the lake house situated alongside a tranquil body of water. The property features a driveway and a garage, surrounded by bare trees, with neighboring structures and boat docks visible in the distance.

Home in Creal Springs

4.5 out of 5 average rating, 4 reviews

Sunset Family Lake House

BryanRating, 5 stars5 days ago

nice house by the lake

Superhost

A wooden deck extends alongside a serene river, surrounded by lush green trees. The water reflects the greenery above, providing a calming natural view. Soft sunlight filters through the leaves, creating a peaceful atmosphere.

Home in House Springs

4.73 out of 5 average rating, 62 reviews

Entire House in House Springs

ShirleyRating, 5 stars2 weeks ago

Our stay here was great! Dzenad was very responsive with any questions I had. It is so peaceful with the river practically in the backyard. I DEFINITELY recommend staying there if you get the chance.

Top guest favorite

A view from the porch features a spacious grassy area, bordered by trees. A comfortable chair is positioned on the wooden floor, inviting relaxation while enjoying the serene surroundings. The sky is overcast, enhancing the green landscape's tranquility.

Cottage in Ava

4.94 out of 5 average rating, 105 reviews

Crazy Joe's Cabin #1

DominiqueRating, 5 stars1 month ago

This little cabin is so nicely finished. Every bit of it was well thought out. It is cozy and it has everything you could need, including a front porch. Its location is relatively close to so many things to do in the area. There are great hikes and beautiful national forest all around the area. I think it's the perfect place for 1-2 people to stay.

Guest favorite

A covered deck is showcased, framed by lush trees and a gravel path. The background features a vibrant sunset illuminating the sky, while the peaceful farm landscape is visible beyond the railing, creating a serene outdoor setting.

Farm stay in Fredericktown

4.93 out of 5 average rating, 328 reviews

NEW DC Farmhouse Come relax in our HOT JACUZZI

ToriRating, 5 stars3 days ago

The home was beautiful ! Very clean and organized! Loved waking up and seeing the cows ! Was able to enjoy the fire pit and the hot tub!

Guest favorite

A covered outdoor seating area is surrounded by large windows, providing views of the lush greenery outside. The space features a wooden table and several chairs, along with a bench. The wooden flooring and ceiling enhance the rustic charm of the setting.

Cabin in Park Hills

4.94 out of 5 average rating, 36 reviews

Private getaway on 4 acres!

MelanieRating, 5 stars1 month ago

This place was perfect for us, and had everything we needed! The keurig and the drip coffee maker, with plenty of coffee, were nice. The beds and furniture were comfortable. The location was great for our family events in Bonne Terre and Fredericktown. We would definitely stay there again!

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Vacation rentals in Chester

Top-rated vacation rentals in Chester

Vacation rentals for every style

Popular amenities for Chester vacation rentals

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