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Vacation rentals in Chester

Find and book unique accommodations on Airbnb

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Popular amenities for Chester vacation rentals

Other great vacation rentals in Chester

Top guest favorite
A view from the loft showcases the open layout of the cabin below. Warm wooden beams support the ceiling, while a cozy sitting area with a dining table and kitchen can be seen. Natural light illuminates the space, enhancing the welcoming ambiance.
Cabin in Perryville
5 out of 5 average rating, 47 reviews

Escape At Eagle View

RebeccaRating, 5 stars1 month ago
We frantically booked at the last minute after our prior plans fell through, and Melissa made the entire process seamless and straightforward! The location was peaceful and lovely and the accommodations were welcoming and cozy. We highly recommend!
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, 648 reviews

The Waterfront cottage

DaneRating, 5 stars1 week ago
This place was a great getaway from the business of every day life. Host was very responsive, and we would 10/10 stay again. The bathtub on the deck is a great feature after dark, and it’s so quiet and peaceful. Lots of games supplied and the loft is an awesome little nook. The 2PM check in is an awesome addition to get your getaway started early. Almost like having another day
Guest favorite
The spacious living area is designed with wooden features and a stone fireplace, creating a rustic ambiance. A large sectional sofa, decorated with vibrant pillows, surrounds a unique, natural wood coffee table. Natural light streams through large windows, illuminating the warm tones of the space.
Home in Ste. Genevieve
5 out of 5 average rating, 70 reviews

Secluded Private Cabin with Pool, hot tub, firepla

EmmaRating, 5 stars1 week ago
This property exceeds 5 stars without a doubt - our only complaint is that we didn’t plan to stay longer!!! We were stopping through on a 5,000 mile road trip & it was like a spot of sheer relaxation & amazingness with something for everyone. The meticulousness of the property was amazing - from the helpful labels to the abundance of towels (for outside & inside) - this property exceeds allll expectations.
Top guest favorite
The spacious kitchen features cream-colored cabinetry and a large island with seating. Pendant lights provide illumination, highlighting the stainless-steel appliances and tile floor. An adjoining dining area with wooden chairs and a large table is visible in the background, bathed in natural light from nearby windows.
Home in Jackson
4.94 out of 5 average rating, 177 reviews

*County Club 439*

ThomasRating, 5 stars1 week ago
This house is a favorite of my family. We chose to stay here again because of the avaible space and the area to entertain my large family. Krista is a great host and does a great job at promptly responding to any question I have. I cannot wait to use this property again.
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 rustic log cabin features a covered porch with wooden railings and chairs. The structure is surrounded by open grassy areas and a clear blue sky with scattered clouds. Natural landscaping completes the serene country setting.
Farm stay in Jackson
4.87 out of 5 average rating, 15 reviews

The Cabins 2

JodiRating, 5 stars4 days ago
We enjoyed our stay in the cozy cabin. The outdoor space was great with a pond, a fire pit, and a charcoal grill. The host was prompt and helpful when communicating.
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 stars4 weeks 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!
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 stars3 weeks 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.

Destinations to explore

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