Chester Vacation Rentals

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Vacation Rentals in Chester

Interior
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 ￥18,839
per night
May 28 - May 29
Downtown historic main street
Fridge, microwave, stovetop, coffee/tea maker
Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, (230)
"Such a quiet peaceful place. It was very clean and did not have that crazy cleaning fee."
The price is ￥23,235
per night
Jun 2 - Jun 3
Beautiful Modern Loft In Wine Country!
Fridge, microwave, oven, stovetop
Private Cabin on Family Farm
10.0 out of 10, Exceptional, (33)
"Great little place in ideal setting. Would come back in a heartbeat."
The price is ￥19,624
per night
Jun 11 - Jun 12
Private Cabin on Family Farm
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Exterior
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
10.0 out of 10, Exceptional, (97)
"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
Pool
Secluded Lodge with Private Lake Minutes from St. Louis
10.0 out of 10, Exceptional, (185)
"Comfortable cozy home right on a small lake. Very quiet and secluded. Home well furnished and hot tub and fire pit are a big bonus!"
Secluded Lodge with Private Lake Minutes from St. Louis
Dining
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
Fridge, microwave, oven, stovetop
Private Home, quiet neighborhood, So. IL, close to St. Louis
10.0 out of 10, Exceptional, (15)
"We booked this beautiful home for our son and daughter-in-laws baby shower. The home is immaculate with every convenience you would need. The backyard has a big deck and overlooks a gorgeous rock wall with a creek running through so there's lots of wildlife. We would absolutely stay here again."
The price is ￥35,323
per night
May 28 - May 29
Private Home, quiet neighborhood, So. IL, close to St. Louis
Property grounds
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
Property grounds
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 ￥15,385
per night
Jun 3 - Jun 4
Cozy 1.5 story bungalow in downtown Ste. Genevieve!
Property grounds
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
10.0 out of 10, Exceptional, (50)
"This was a perfect cabin for our family weekend. The cabin is clean and comfortable. There are many small, charming details. The doors and stairs add to the rustic feel of the home. The owner and his adorable helpers were there to greet us, but then gave us privacy. I am sure this will not be our last visit, as everyone loved the cabin. I highly recommend it for anybody staying in this area."
The price is ￥54,947
per night
Jun 2 - Jun 3
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Fridge, microwave, oven, stovetop
"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 ￥20,723
per night
Jun 3 - Jun 4
"Little Brick House on Main (1865)”
Pool
Homestead Hideaway + Hot Tub
9.8 out of 10, Exceptional, (15)
"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 ￥18,054
per night
Jun 2 - Jun 3
Homestead Hideaway + Hot Tub
4 bedrooms, iron/ironing board, bed sheets
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
Exterior
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (62)
"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
Exterior
Countryside Private Guest Room
10.0 out of 10, Exceptional, (7)
"Hosts were very friendly and quick with accepting request. Also very quick to give check in information."
The price is ￥11,774
per night
May 29 - May 30
Countryside Private Guest Room
Fridge, microwave, oven, stovetop
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (115)
"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
House | Living area
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 ￥29,819
per night
May 28 - May 29
Tiny Houses of French Village
Property grounds
Peter Ray House
10.0 out of 10, Exceptional, (46)
"This is an amazing property. The home is beautiful and very period appropriate. It felt like home. The front porch was very relaxing. We loved sitting outside and relaxing. This home was immaculate on the inside, with plenty of room for the 3 of us. I can not say enough about this home. We will definitely be back to visit."
The price is ￥23,549
per night
May 28 - May 29
Peter Ray House
Property grounds
Sweet Farm Stay
10.0 out of 10, Exceptional, (16)
"We didn't get to spend as much time on the property as we would have liked but we enjoyed our time. It was a peaceful spot on a secluded property. Meeting Dexter the Donkey and the cats on the property, as well as enjoying the scenery, was the highlight. The house is quant, maybe a little cluttered with unnecessary furniture making the spaces feel a little small, but we loved all of the plant life and nostalgia as well as the coffee area. The upstairs was a little rough for sleeping as the...
The price is ￥23,549
per night
May 29 - May 30
Sweet Farm Stay
55-inch Smart TV with digital channels, TV, streaming services
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 ￥21,365
per night
Jun 14 - Jun 15
Urban Lofts
Don't see what you're looking for?
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

Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Pillowtop beds, desk, iron/ironing board, cribs/infant beds
Best Western Chester Hotel
2.5 star property
8.6 out of 10, Excellent, (250)
"Very nice staff and clean room. I do wish there was more work out equipment. "
The price is ￥13,719
per night
Jun 2 - Jun 3
Best Western Chester Hotel
Lobby
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 star property
8.0 out of 10, Very Good, (612)
"Clean and located in a decent area"
The price is ￥14,545
per night
Jun 23 - Jun 24
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Exterior
Super 8 by Wyndham Perryville
2.0 star property
8.6 out of 10, Excellent, (740)
"I stay here very often its a great place"
The price is ￥10,008
per night
Jun 2 - Jun 3
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.

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Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we give you a choice of vacation rentals in Chester near Chester Skating Rink, or you can choose a 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 vacation home rentals that Chester has to offer?

The 1801 House: A beautiful historic home in the Ste Genevieve Historic District: This vacation home rental outside of Chester is located in the city center and has a patio, a garden, and a barbecue grill 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 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 vacation rentals like in Chester?

Vacation rentals are private accommodations you can stay in for a short or long stay in Chester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.

Recent reviews of Chester properties
Expedia verified reviews

Super 8 by Wyndham Okawville

Super 8 by Wyndham Okawville

5/5 Excellent
"As with all hotels, the floor in the room always turns my socks brown but otherwise, a decent hotel. Felt safe and it was quiet. We traveled with two toddlers. All was fine."
A verified traveler stayed at Super 8 by Wyndham Okawville
Posted 4 days ago
Super 8 by Wyndham Okawville