Vacation rentals in Chester

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Popular amenities for Chester vacation rentals

Other great vacation rentals in Chester

Top guest favorite
A charming exterior of a 1930s home features a distinct front door with a rounded window, framed by decorative awnings. Low-maintenance landscaping showcases pebbles and shrubs, while two steps lead up to the door, flanked by a decorative railing.
Cottage in Ste. Genevieve
5 out of 5 average rating, 72 reviews

MorLy Cottage Downtown

MelindaRating, 5 stars5 days ago
My husband and I love staying at Morley Cottage. Just the right space and everything we need in walking distance. Our host has made our stay easy and flexible for arrival and departure. We’re happy to call Morley Cottage our home away from home oasis. Thank you!
Superhost
An attic-style room features two beds with gray plaid blankets, situated on polished wooden floors. A vintage tricycle rests against the wall, and natural light streams in through a door leading to a small outdoor space.
Cottage in Pinckneyville
4.82 out of 5 average rating, 71 reviews

Cozy cottage in peaceful setting.

SashaRating, 5 stars3 weeks ago
For being one of the smallest, most rural air bnbs we have ever stayed in- Though it really wasn't even small (3 bed, 2 rooms, 2 bath!) I have to say I was thoroughly impressed! This was honestly one of the nicest air bnbs weve ever stayed in! It was quiet, private, cozy and while I was initially disappointed having overlooked the no TV part i quickly grew to love the vibe this place brought over our two days here! The kids enjoyed having their own space upstairs while we got to be downstairs. There's an adorable little area that my husband and I quietly had our coffee in and the kitchen was adorned with brand new appliances that were squeaky clean. The owner clearly has great taste bc everything from the handsoap to the hand towels was amazing scents and good quality 😂 This was definitely worth the money and we cant wait to come back next summer!
Guest favorite
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
4.92 out of 5 average rating, 155 reviews

Coeur de la Crème Suite at Baetje Farms

TaylorRating, 5 stars1 day ago
Had an amazing stay! The Airbnb was pristine and the property is quiet and peaceful. Had a great time feeding the goats and hiked nearby at Pickle Springs. Would definitely stay again!
Top guest favorite
Cottage in Farmington
4.97 out of 5 average rating, 58 reviews

Parsons Cottage

SamanthaRating, 5 stars1 week ago
We had an amazing stay at the cottage. It was beautiful and had everything we could need for our family of six. The games were a hit for our kids and we enjoyed waffles in the morning! Would definitely love to come back!
Guest favorite
A modern glass shower enclosure is showcased, featuring white subway tiles and a sleek floor. Grab bars are placed for accessibility, and natural light highlights the clean lines of the space. A minimalist aesthetic is created by the polished finishes and open design.
Home in Steeleville
5 out of 5 average rating, 8 reviews

Tiny house near town.

JenniferRating, 5 stars1 week ago
Loved the quietness and comfort. Location was perfect. Close to my family that lives there. House was cute and had everything we needed for the short time we were there. Was a great place to go to at the end of each day. My daughter and I loved listening to the frogs and watching the fireflies out in the back area. Will definitely come back!
Top guest favorite
Two individuals are standing together in a garden setting, surrounded by vibrant tropical plants. The woman is wearing a colorful floral dress, while the man is dressed in a patterned shirt. A warm, welcoming atmosphere is conveyed by the greenery and soft lighting in the background.
Cabin in Steeleville
4.97 out of 5 average rating, 70 reviews

Cabin By The Woods -Country Living at it's Best!

VirginiaRating, 5 stars7 months ago
Wow! Wow! Wow! I rented this cabin for my husband and a few friends that went to Illinois for a hunting trip. I literally cannot say enough great things about this place and about Wally & Vickie. To say that they went above and beyond would be an understatement. Wally seriously went out of his way to accommodate my husband and his friends. His kindess and generosity did not go unnoticed. In addition to the gracious host, the cabin itself was beautiful, clean, and well stocked to meet all of our groups' needs. My husband is already looking forward to renting this space again next year!
Guest favorite
A spacious interior of a bar is shown, featuring wooden tables and chairs arranged throughout the space. The bar area is prominently located in the background, with a television displaying a sports game. Warm lighting creates a welcoming ambiance.
Home in Altenburg
4.88 out of 5 average rating, 33 reviews

Historic House in the heart of Altenburg

GeoffRating, 5 stars5 months ago
If you are looking for a nice old house in a neat little town this is it. We had our family visit us from the area and it was a perfect place to host from. The kitchen was well stocked and made cooking a breeze. Also the host was very responsive to any questions we had about the house and the area. We will definitely stay here again if we will be in the area!
Top guest favorite
A compact kitchen area is equipped with countertop space and a sink. Shelves hold dishes, mugs, and glassware, while a coffee maker is positioned near clean dishes drying in a rack. A microwave is mounted above the counter, surrounded by light-colored cabinetry.
Apartment in Carbondale
4.96 out of 5 average rating, 47 reviews

Regal Rustic Retreat

AmandaRating, 5 stars6 days ago
Perfect peaceful place to stay while we did some hiking and then wine trails. Everything was as described and all drawers and light switches were labeled which was really nice.

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