Chester Holiday Rentals

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Holiday Rentals in Chester

The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
10.0 out of 10, Exceptional, (98)
"We needed an interesting place to visit that was not a big city. We wanted a nice relaxing environment. St Genevieve and the 1801 House met our expectations. The hosts thought of everything their guests would need. The kitchen was equipped with everything we needed to prepare meals. I will recommend this property to others."
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, (231)
"My fiancé had a romantic getaway at the goose hill loft. The property is beautiful and the loft was very spacious. I highly recommend this property for both couples and small families."
The price is NZ$293
per night
12 Jun - 13 Jun
Beautiful Modern Loft In Wine Country!
Downtown historic main street
9.6 out of 10, Exceptional, (161)
"The price it says is not accurate, it says it fits 6 but u are charged 25 for each person on top of price of stay."
The price is NZ$233
per night
10 Jun - 11 Jun
Downtown historic main street
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"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (26)
"We took an impromptu overnight from St. Louis. Wonderful place in a nice area. Lots of places to see."
The price is NZ$282
per night
10 Jun - 11 Jun
"Little Brick House on Main (1865)”
Secluded Lodge with Private Lake Minutes from St. Louis
10.0 out of 10, Exceptional, (187)
"Spacious cabin with plentiful amenities. Hosts are very responsive and helpful. Great fishing and very comfortable."
Secluded Lodge with Private Lake Minutes from St. Louis
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
10.0 out of 10, Exceptional, (98)
"Excellent location. Very quiet"
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Private Cabin on Family Farm
10.0 out of 10, Exceptional, (35)
"Beautiful location. Peaceful setting. Loved seeing the lightning bugs and listening to the bullfrogs at night. Owner, Tom, very kind and friendly. Bought lots of delicious items in their store. Apple cider doughnuts were a hit!"
The price is NZ$401
per night
17 Jun - 18 Jun
Private Cabin on Family Farm
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
10.0 out of 10, Exceptional, (4)
"Would stay here again!"
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
10.0 out of 10, Exceptional, (148)
"Would stay again."
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Countryside Private Guest Room
10.0 out of 10, Exceptional, (8)
"Wonderful experience. Host was attentive and responded quickly to any questions. I will stay here again!!"
The price is NZ$156
per night
11 Jun - 12 Jun
Countryside Private Guest Room
Cozy Haven Guest Cottage Pet Friendly Sleeps 4
10.0 out of 10, Exceptional, (26)
"Clean, comfy and wonderful communication with owners! Everything was perfect! Will be contacting this owner in the future!"
Cozy Haven Guest Cottage Pet Friendly Sleeps 4
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
10.0 out of 10, Exceptional, (51)
"Beautiful tranquil and very roomy !! Perfect place to stay !!"
The price is NZ$745
per night
10 Jun - 11 Jun
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Homestead Hideaway + Hot Tub
9.8 out of 10, Exceptional, (16)
"Homestead Hideaway was perfect for our girls party! The bedrooms were comfy as was the living room. The living room was perfect for hanging out and relaxing, best couch ever! The host's communication was great, she was very easy to contact. Totally recommend it, it met and exceeded our expectations!"
The price is NZ$370
per night
12 Jun - 13 Jun
Homestead Hideaway + Hot Tub
Private Home, quiet neighborhood, So. IL, close to St. Louis
10.0 out of 10, Exceptional, (16)
"I booked this house for my parents, who traveled 14+ hours for a funeral. My mom & Dad loved the place, commented on how nice it was, and how convenient it was, considering the nearest hotels we're far away and cost just as much. They also said that next time they were in town, they'd look to see if this house was available."
The price is NZ$539
per night
12 Jun - 13 Jun
Private Home, quiet neighborhood, So. IL, close to St. Louis
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (63)
"We held our family Christmas here. 13 people, 7 adults and 6 children. We spent 6 days here. People played pool, ping pong, games, swam and we grilled outside. This house has everything you would in your own home! One day I hosted our huge family gathering of 40+people, plenty of room, it was nice outside and inside and once again everything is provided at the house. I would recommend this house to everyone. Beautiful home. I will rent this house again. Julie"
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Country Home for the Family
10.0 out of 10, Exceptional, (26)
"For all men's plenty of room all, had a wonderful time"
Country Home for the Family
Cozy 1.5 story bungalow in downtown Ste. Genevieve!
9.6 out of 10, Exceptional, (8)
"Cute little bungalow perfect for a couple. Walking distance to shops and restaurants"
The price is NZ$236
per night
10 Jun - 11 Jun
Cozy 1.5 story bungalow in downtown Ste. Genevieve!
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 NZ$418
per night
10 Jun - 11 Jun
Tiny Houses of French Village
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (116)
"We had an excellent experience at the Bauman’s Hillside Hideaway. It was spacious enough to accommodate our large family. The fireplace and fire pit were great additions to add to our visit. The game room had something for everyone."
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Urban Lofts
3.0 star property
9.0 out of 10, Wonderful, (14)
"Great place and will stay again when in the area!!!"
The price is NZ$311
per night
14 Jun - 15 Jun
Urban Lofts
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See all available properties in Chester
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.

Other types of properties in Chester you may be interested in

Best Western Chester Hotel
2.5 star property
8.6 out of 10, Excellent, (253)
"Quiet, good service,good breakfast "
The price is NZ$151
per night
16 Jun - 17 Jun
Best Western Chester Hotel
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 star property
8.0 out of 10, Very good, (615)
"The rooms are clean. The communal are is under some renovation, but the breakfast is excellent. The public areas aren't as neat as I normally like, though. Good thing the rooms are clean and neat, though."
The price is NZ$175
per night
17 Jun - 18 Jun
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Super 8 by Wyndham Perryville
2.0 star property
8.6 out of 10, Excellent, (744)
"Everyone was friendly. Room clean & comfortable, had a nice breakfast selection. Pool was clean as well as the area around it. The outside area was very clean as well. Only thing I wish they had iced coffee. "
The price is NZ$120
per night
16 Jun - 17 Jun
Super 8 by Wyndham Perryville
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chester. Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chester short-term rentals, that won’t be hard to do.

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.

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