Chester Vacation Rentals

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Vacation Rentals in Chester

The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
Exterior
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
10.0 out of 10, Exceptional, 98 reviews
"Loved our stay here. Quaint town, beautiful and well appointed home, and lots to do in the area - wineries, hiking, walks around town, hilly runs and nice restaurants. We’d return!"
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
Beautiful Modern Loft In Wine Country!
Fridge, microwave, stovetop, coffee/tea maker
Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, 231 reviews
"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 CA $202
CA $244 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Modern Loft In Wine Country!
Downtown historic main street
Interior
Downtown historic main street
9.6 out of 10, Exceptional, 161 reviews
"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 CA $164
CA $195 total
includes taxes & fees
Jun 10 - Jun 11
Downtown historic main street
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"Little Brick House on Main (1865)”
Fridge, microwave, oven, stovetop
"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, 26 reviews
"We took an impromptu overnight from St. Louis. Wonderful place in a nice area. Lots of places to see."
The price is CA $180
CA $235 total
includes taxes & fees
Jun 10 - Jun 11
"Little Brick House on Main (1865)”
Secluded Lodge with Private Lake Minutes from St. Louis
Pool
Secluded Lodge with Private Lake Minutes from St. Louis
10.0 out of 10, Exceptional, 187 reviews
"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
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Dining
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
10.0 out of 10, Exceptional, 98 reviews
"Excellent location. Very quiet"
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Private Cabin on Family Farm
Fridge, microwave, oven, stovetop
Private Cabin on Family Farm
10.0 out of 10, Exceptional, 35 reviews
"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 CA $171
CA $335 total
includes taxes & fees
Jun 11 - Jun 12
Private Cabin on Family Farm
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
Exterior
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
10.0 out of 10, Exceptional, 4 reviews
"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
Property grounds
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
10.0 out of 10, Exceptional, 148 reviews
"Would stay again."
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Countryside Private Guest Room
Exterior
Countryside Private Guest Room
10.0 out of 10, Exceptional, 8 reviews
"Wonderful experience. Host was attentive and responded quickly to any questions. I will stay here again!!"
The price is CA $103
CA $130 total
includes taxes & fees
Jun 8 - Jun 9
Countryside Private Guest Room
Cozy Haven Guest Cottage Pet Friendly Sleeps 4
Property grounds
Cozy Haven Guest Cottage Pet Friendly Sleeps 4
10.0 out of 10, Exceptional, 26 reviews
"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.
Property grounds
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
10.0 out of 10, Exceptional, 51 reviews
"Beautiful tranquil and very roomy !! Perfect place to stay !!"
The price is CA $478
CA $622 total
includes taxes & fees
Jun 10 - Jun 11
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Homestead Hideaway + Hot Tub
Pool
Homestead Hideaway + Hot Tub
9.8 out of 10, Exceptional, 15 reviews
"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 CA $164
CA $309 total
includes taxes & fees
Jun 12 - Jun 13
Homestead Hideaway + Hot Tub
Private Home, quiet neighborhood, So. IL, close to St. Louis
Fridge, microwave, oven, stovetop
Private Home, quiet neighborhood, So. IL, close to St. Louis
10.0 out of 10, Exceptional, 16 reviews
"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 CA $308
CA $450 total
includes taxes & fees
Jun 9 - Jun 10
Private Home, quiet neighborhood, So. IL, close to St. Louis
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Exterior
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, 63 reviews
"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
4 bedrooms, iron/ironing board, bed sheets
Country Home for the Family
10.0 out of 10, Exceptional, 26 reviews
"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!
Property grounds
Cozy 1.5 story bungalow in downtown Ste. Genevieve!
9.6 out of 10, Exceptional, 8 reviews
"Cute little bungalow perfect for a couple. Walking distance to shops and restaurants"
The price is CA $134
CA $197 total
includes taxes & fees
Jun 10 - Jun 11
Cozy 1.5 story bungalow in downtown Ste. Genevieve!
Tiny Houses of French Village
House | Living area
Tiny Houses of French Village
2.5 star property
10.0 out of 10, Exceptional, 2 reviews
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
The price is CA $260
CA $418 total
includes taxes & fees
Jun 9 - Jun 10
Tiny Houses of French Village
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Fridge, microwave, oven, stovetop
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, 116 reviews
"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
55-inch Smart TV with digital channels, TV, streaming services
Urban Lofts
3.0 star property
9.0 out of 10, Wonderful, 14 reviews
"Great place and will stay again when in the area!!!"
The price is CA $186
CA $301 total
includes taxes & fees
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

Best Western Chester Hotel
Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave
Best Western Chester Hotel
2.5 star property
8.6 out of 10, Excellent, 252 reviews
"Quiet, good service,good breakfast "
The price is CA $107
CA $119 total
includes taxes & fees
Jun 12 - Jun 13
Best Western Chester Hotel
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Lobby
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 star property
8.0 out of 10, Very good, 614 reviews
"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 CA $128
CA $146 total
includes taxes & fees
Jun 18 - Jun 19
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Super 8 by Wyndham Perryville
Exterior
Super 8 by Wyndham Perryville
2.0 star property
8.6 out of 10, Excellent, 743 reviews
"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 CA $87
CA $100 total
includes taxes & fees
Jun 18 - Jun 19
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.

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester vacation rentals we have selected for you start as low as CA $103 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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

Private Cabin on Family Farm

Private Cabin on Family Farm

5/5 Excellent
Lovely get away
"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!"
A verified traveller stayed at Private Cabin on Family Farm
Posted 20 hours ago
Private Cabin on Family Farm