Holiday houses in Chester

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Popular amenities for Chester holiday rentals

Other great holiday rentals in Chester

Top Guest favourite
Cottage in Ste. Genevieve
5 out of 5 average rating, 72 reviews

MorLy Cottage Downtown

MelindaRating, 5 stars6 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
Cottage in Pinckneyville
4.82 out of 5 average rating, 71 reviews

Cozy cottage in peaceful setting.

SashaRating, 5 stars4 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 favourite
Tiny home in Bloomsdale
4.92 out of 5 average rating, 155 reviews

Coeur de la Crème Suite at Baetje Farms

TaylorRating, 5 stars2 days 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 favourite
Cottage in Farmington
4.97 out of 5 average rating, 59 reviews

Parsons Cottage

ChristinaRating, 5 stars2 days ago
Thank you so much for having us! We had a great time. Such a cute and cozy home!! I love the charm of the home and vintage dishes. It felt like home away from home. We want to come back soon :)
Guest favourite
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 favourite
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 favourite
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 favourite
Apartment in Carbondale
4.96 out of 5 average rating, 47 reviews

Regal Rustic Retreat

AmandaRating, 5 stars1 week 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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