Chester Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Chester

Exterior
Private Cabin with Pond on Family Farm

Private Cabin with Pond on Family Farm

Belleville
10.0 out of 10, Exceptional, (93)
"The cabin is the perfect place to visit with our family. Quiet location on an orchard. Cabin is fully equipped for multi - day visits. Tom Range is a wonderful host."
United States
Charlie O.
Private Cabin with Pond on Family Farm
Exterior detail
"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”

Ste. Genevieve
10.0 out of 10, Exceptional, (62)
"Great place to stay!"
United States
Lettitia B.
The price is HK$923
HK$1,234 total
includes taxes & fees
16 Nov - 17 Nov
"Little Brick House on Main (1865)”
Interior
Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4

Ste.Genevieve
9.8 out of 10, Exceptional, (52)
"Great host and a cozy place to stay "
United States
Ashlynn P.
Cozy Haven Little Hidden Gem Sleeps 4
Exterior
In the Country a Beautiful 2-bedroom house with its own private lake

In the Country a Beautiful 2-bedroom house with its own private lake

Waterloo
10.0 out of 10, Exceptional, (5)
The price is HK$1,224
HK$1,957 total
includes taxes & fees
20 Nov - 21 Nov
In the Country a Beautiful 2-bedroom house with its own private lake
Terrace/patio
Secluded Lodge with Private Lake Minutes from St. Louis

Secluded Lodge with Private Lake Minutes from St. Louis

Millstadt
10.0 out of 10, Exceptional, (211)
"Great hospitality had everything you needed"
United States
michael k.
Secluded Lodge with Private Lake Minutes from St. Louis
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!

Ste. Genevieve
10.0 out of 10, Exceptional, (270)
"Beautiful loft on beautiful property!"
United States
Addison G.
The price is HK$1,150
HK$1,405 total
includes taxes & fees
24 Nov - 25 Nov
Beautiful Modern Loft In Wine Country!
Fridge, microwave, oven, stovetop
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

2.0 star property
Ste. Genevieve
10.0 out of 10, Exceptional, (15)
"Awesome from checking in to all of the place was excellent!!"
United States
Michelle A.
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Outdoor dining
Doves Nest Guest House<br> Tranquil & Relaxing

Doves Nest Guest House<br> Tranquil & Relaxing

Ste. Genevieve
10.0 out of 10, Exceptional, (53)
"We loved our time here! I got married this past Sunday and my bridesmaids and I stayed here before the wedding! It was absolutely perfect!"
United States
Terra L.
The price is HK$1,259
HK$2,083 total
includes taxes & fees
17 Nov - 18 Nov
Doves Nest Guest House<br> Tranquil & Relaxing
Outdoor dining
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Ste. Genevieve
10.0 out of 10, Exceptional, (58)
"My son's wedding was at Pebble Creek Farms and having this cabin was great because my the whole family could stay together in one spot. It was roomy , super clean and very peaceful. "
United States
Janet G.
The price is HK$2,099
HK$2,806 total
includes taxes & fees
16 Nov - 17 Nov
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Fridge, microwave, oven, stovetop
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Ste. Genevieve
10.0 out of 10, Exceptional, (136)
"It’s perfect and already booking next year!"
United States
Joan H.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Fridge, microwave, oven, stovetop
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

New Offenburg
10.0 out of 10, Exceptional, (4)
"Very clean - host was easy to work with. "
United States
Jamie M.
The price is HK$1,166
HK$2,331 total
includes taxes & fees
16 Nov - 17 Nov
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Property grounds
Peter Ray House

Peter Ray House

Maeystown
10.0 out of 10, Exceptional, (70)
"The house was wonderful, the town was delightful, and the people were very friendly! We can’t wait for our next trip!"
United States
Deborah
The price is HK$1,049
HK$1,746 total
includes taxes & fees
23 Nov - 24 Nov
Peter Ray House
Exterior
Hot Tub & Creek Views: Secluded Perryville Cabin

Hot Tub & Creek Views: Secluded Perryville Cabin

Perryville
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay! Peaceful and relaxing.John and Bambi"
United States
Bambi and John B.
Hot Tub & Creek Views: Secluded Perryville Cabin
Interior
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

Ste. Genevieve
10.0 out of 10, Exceptional, (4)
"This home looks exactly like the picture. It is so cute and soooo clean!!!! It was very convenient to the wedding venue I was in town for. Communication was top notch and to top it off, I lost my car key in the driveway, and they shipped it back to me. Highly recommend this property! "
United States
Sheree B.
The price is HK$1,532
HK$1,991 total
includes taxes & fees
18 Nov - 19 Nov
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Property grounds
TreeLoft at BaseCamp

TreeLoft at BaseCamp

2.0 star property
Perryville
10.0 out of 10, Exceptional, (5)
"This place is perfect if you want a private upscale experience that is immersed in natural beauty. The treehouse is luxurious and so comfortable. We loved every minute of our stay. "
United States
joel r.
The price is HK$2,324
HK$3,870 total
includes taxes & fees
14 Dec - 15 Dec
TreeLoft at BaseCamp
Interior
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

3.0 star property
Murphysboro
10.0 out of 10, Exceptional, (1)
"This is a very clean and nice apartment within a very close drive to the Kinkaid boat launch. Easy to locate and can fit a car with a boat in tow no problem. This spot was also much more quiet than the campground or RV spots nearby. They have a great porch and a grill and we didn’t bring something for it which made me sad. "
United States
Ross
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Dining
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Bloomsdale
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay. The home and property were absolutely beautiful and Julie went above and beyond to accommodate us. I can't wait to go back."
United States
Jennifer M.
The price is HK$1,399
HK$2,155 total
includes taxes & fees
16 Dec - 17 Dec
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Property grounds
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Ste. Genevieve
10.0 out of 10, Exceptional, (174)
"We loved staying here!! The host is amazing and it feels like home away from home!"
United States
Mia S.
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Property grounds
Historic House in heart of Altenburg

Historic House in heart of Altenburg

2.0 star property
Altenburg
Historic House in heart of Altenburg
Outdoor spa tub
Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub

Fults
10.0 out of 10, Exceptional, (27)
"We were having a family reunion in the area and this quiet, relaxing get away spot provided a clean and private country home for us to stay for the weekend."
United States
Carol F.
The price is HK$1,010
HK$1,919 total
includes taxes & fees
16 Dec - 17 Dec
Homestead Hideaway + Hot Tub
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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Top Chester Hotel Reviews

Microtel Inn & Suites by Wyndham Sainte Genevieve

Microtel Inn & Suites by Wyndham Sainte Genevieve

10/10 Excellent
"Excellent "
James 4-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Sainte Genevieve

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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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 holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, 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?

In the Country a Beautiful 2-bedroom house with its own private lake: This holiday home rental outside of Chester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Popeye Museum is one of the cultural attractions. Other places in town to visit include Fort Kaskaskia and Kaskaskia Bell.

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.