Chester Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chester

Downtown historic main street
9.6 out of 10, Exceptional, (176)
"The area was very eclectic and fun. Very unique area. Needs a little work yet but was informed of that from the get go. "
The price is AU$222
includes taxes & fees
27 Nov - 28 Nov
Downtown historic main street
Private Cabin with Pond on Family Farm
10.0 out of 10, Exceptional, (56)
"We are here visiting family and needed a peaceful place to stay. This was exactly what we needed. When we come back to the area, we WILL stay here. Thank you for a great vacation "
Private Cabin with Pond on Family Farm
Secluded Lodge with Private Lake Minutes from St. Louis
10.0 out of 10, Exceptional, (196)
"My best friend of 50 years and I spent four days at this lovely house. The hosts were wonderful; answered any questions we had very promptly. We are both in our 70s and the stairs were more of a challenge than I had anticipated from the pictures, but we managed. The house is lovely, the grounds are great and the fishing was awesome. We would definitely recommend this or a quiet getaway, especially if you like to fish."
Secluded Lodge with Private Lake Minutes from St. Louis
Sweet Farm Stay
10.0 out of 10, Exceptional, (24)
"We only spent one evening there, but it was peaceful and lovely!"
The price is AU$266
includes taxes & fees
25 Nov - 26 Nov
Sweet Farm Stay
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (121)
"We came in town for a short weekend, as a group of 14. Plenty of room for all of us and lots of activities for all ages. The kitchen is very well stocked with everything you could need. We are already talking about returning to this property, or the neighboring one. Thanks, Emma for your hospitality! "
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Countryside Private Guest Room
10.0 out of 10, Exceptional, (11)
"The room was clean & well kept. Everything we needed was already there. Toiletries, towels, bedding, coffee, bottled water & more. Beautiful property & very quiet. The host were very nice folks. We would definitely stay again. "
The price is AU$149
includes taxes & fees
25 Nov - 26 Nov
Countryside Private Guest Room
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
10.0 out of 10, Exceptional, (14)
"Great spot close to some family local. "
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Country Home for the Family
10.0 out of 10, Exceptional, (30)
"We loved having room indoors to gather and outdoors to play."
Country Home for the Family
Tiny Houses of French Village
2.5 star property
10.0 out of 10, Exceptional, (2)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
The price is AU$469
includes taxes & fees
24 Nov - 25 Nov
Tiny Houses of French Village
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
10.0 out of 10, Exceptional, (110)
"We have stayed here before and absolutely love it. Very cozy. Convenient and good communication with owner. "
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Ste. Genevieve Co. House w/ HOT TUB!
9.6 out of 10, Exceptional, (5)
"The property could use an update but it was good for what we needed"
Ste. Genevieve Co. House w/ HOT TUB!
Cozy Haven Little Hidden Gem Sleeps 4
10.0 out of 10, Exceptional, (36)
"I will absolutely be returning! "
Cozy Haven Little Hidden Gem Sleeps 4
Peter Ray House
10.0 out of 10, Exceptional, (58)
"Was so happy staying here - satisfied in every way. The house was just as described (even better than I expected), clean, and comfortable. Communication with Joyce was excellent - she was always available, and very descriptive with the overall checkin/checkout process. I would stay here again in a heartbeat. (:"
Peter Ray House
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
10.0 out of 10, Exceptional, (111)
"This is a very charming and cozy house. It was very clean and the appliances were all new/newer. The home has 1 queen bed, 1 full bed, and 1 king. They also have a blow up bed in the closet. Great selection of k cup coffees and tea bags. A very special surprise of gooey butter cakes from Pats, the local pastry shop."
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
Private Home, quiet neighborhood, So. IL, close to St. Louis
10.0 out of 10, Exceptional, (18)
"We are repeat stayers in this home and appreciate all the comforts of the property each year! The host is the best in always leaving snacks and beverages; and all the things you would need for a long stay!"
The price is AU$512
includes taxes & fees
30 Nov - 1 Dec
Private Home, quiet neighborhood, So. IL, close to St. Louis
"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (39)
"We were there for our grandson's wedding. This little house exceeded all expectation. Just lovely and with so many extra thoughtful touches, i.e. pumpkins and fall flowers for cozy October. Too many to list. "
The price is AU$269
includes taxes & fees
24 Nov - 25 Nov
"Little Brick House on Main (1865)”
Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, (242)
"Hands down the best vrbo stay I've ever had. Super clean, amazing views and close to several places to hike. Its a must stay!"
The price is AU$278
includes taxes & fees
3 Dec - 4 Dec
Beautiful Modern Loft In Wine Country!
Homestead Hideaway + Hot Tub
9.8 out of 10, Exceptional, (20)
"My family and I travel every year in August to attend the Grand All American Shooting Event, this has been the best stay by far. Felt like we were right at home"
The price is AU$354
includes taxes & fees
4 Dec - 5 Dec
Homestead Hideaway + Hot Tub
Missouri Castle w/ Private Lake, Pool & 100 Acres!
10.0 out of 10, Exceptional, (2)
"Our group stayed here after a larger family reunion at Trout Lodge, YMCA. The place was great with something to do for everyone. Having a private, CLEAN pool for the family is amazing. We hiked around and boated around the lake, made s’mores by a campfire, played pool and darts and board games and grilled meals. This house lets you do it all and has the space to visit family and also have alone time. I’d love to come back."
Missouri Castle w/ Private Lake, Pool & 100 Acres!
CWR Cottage - A cozy cottage in a quiet country setting
8.8 out of 10, Excellent, (8)
"I booked this place as a home base for chasing the eclipse back in April. As far as "small" places go, I loved this one. A nice open layout makes it easy for you to unpack and maneuver around. I was traveling between St. Louis and Carbondale during my stay and I liked the small, quaint area the home is located. It's about a 45 minute drive from St. Louis and the drive back to the home at night was very peaceful on the country roads. It had everything I needed for my trip and I wish I could have...
CWR Cottage - A cozy cottage in a quiet country setting
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chester you may be interested in

Baymont by Wyndham Chester IL
2.5 star property
8.6 out of 10, Excellent, (275)
"room was right by the breakfast area and ice machine could hear everything"
The price is AU$146
includes taxes & fees
8 Dec - 9 Dec
Baymont by Wyndham Chester IL
Holiday Inn Express & Suites Perryville, an IHG Hotel
2.5 star property
9.4 out of 10, Exceptional, (422)
"Very clean property the rooms were very clean and like new. The breakfast was your typical hotel breakfast. I would recommend staying here if you come to Perryville"
The price is AU$174
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express & Suites Perryville, an IHG Hotel
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 star property
8.0 out of 10, Very good, (703)
"Friendliness, very clean, very quiet and very good location."
The price is AU$154
includes taxes & fees
10 Dec - 11 Dec
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Chester Skating Rink, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its golf courses and parks. Make sure you have time to check out the restaurants and entertainment choices during your trip.

What are some of the best holiday rentals that Chester has to offer?

The 1801 House: A beautiful historic home in the Ste Genevieve Historic District: This holiday home rental outside of Chester is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chester Skating Rink. Other places in town to visit include Fort Kaskaskia and Popeye Museum.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.