Chester Holiday Rentals

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Our top choices for Chester holiday rentals

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
2.0 star property
French Village
9.8 out of 10, Exceptional, (48 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is AU$186
includes taxes & fees
26 Jan - 27 Jan
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (3 reviews)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
United States
Norma
Tiny Houses of French Village

⚜️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, (19 reviews)
"Great historic property!"
United States
Rhonda R.
The price is AU$318
includes taxes & fees
25 Jan - 26 Jan
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is AU$141
includes taxes & fees
25 Jan - 26 Jan
Countryside Private Guest Room

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
2.0 star property
Oraville
10.0 out of 10, Exceptional, (3 reviews)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is AU$342
includes taxes & fees
26 Jan - 27 Jan
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

New! Luxury Meets Nature - TreeRise at BaseCamp

New! Luxury Meets Nature - TreeRise at BaseCamp
2.0 star property
Perryville
10.0 out of 10, Exceptional, (4 reviews)
"Had the best stay. Loved the cozy feel. Loved the hot tub right outside the bedroom. "
United States
Kathleen F.
The price is AU$931
includes taxes & fees
15 Feb - 16 Feb
New! Luxury Meets Nature - TreeRise at BaseCamp

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (48 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is AU$360
includes taxes & fees
1 Feb - 2 Feb
Peaceful Country Home

Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay. Kitchen not real well stocked and no WiFi but perfect for what we needed. "
United States
Brandon H.
The price is AU$307
includes taxes & fees
30 Jan - 31 Jan
Fit and Fueled Studio

Gorgeous, downtown house!

Gorgeous, downtown house!
Perryville
10.0 out of 10, Exceptional, (1 review)
"Our stay was excellent and our host Carisa was a Great person to work with. The house was beautiful. The house worked out great for us. We had 6 people staying and we all had very comfortable beds and our own bathrooms. Great for a large family. "
United States
Doyle or Cheryl D.
The price is AU$1,266
includes taxes & fees
21 Jan - 22 Jan
Gorgeous, downtown house!

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (64 reviews)
"Great place to stay!"
United States
Lettitia B.
The price is AU$240
includes taxes & fees
23 Jan - 24 Jan
"Little Brick House on Main (1865)”

Retreat Air - King Bed, Hot Tub & No cleaning fee

Retreat Air - King Bed, Hot Tub & No cleaning fee
2.0 star property
Perryville
The price is AU$234
includes taxes & fees
20 Feb - 21 Feb
Retreat Air - King Bed, Hot Tub & No cleaning fee

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (71 reviews)
"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 AU$332
includes taxes & fees
21 Jan - 22 Jan
Peter Ray House

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is AU$376
includes taxes & fees
26 Jan - 27 Jan
Homestead Hideaway + Hot Tub

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 reviews)
"Clean spacious quiet( except for the dogs barking) kitchen pans are terrible."
United States
Barb S.
The price is AU$531
includes taxes & fees
28 Jan - 29 Jan
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant

Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant
Perryville
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!"
United States
Thor L.
The price is AU$475
includes taxes & fees
21 Jan - 22 Jan
Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (272 reviews)
"Loved our stay here! Thoughtful amenities on a beautiful property. Great communication with host. "
United States
Elsie H.
The price is AU$269
includes taxes & fees
23 Jan - 24 Jan
Beautiful Modern Loft In Wine Country!

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
The price is AU$262
includes taxes & fees
21 Jan - 22 Jan
Fishing Cabin next to Kinkaid Lake

Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (4 reviews)
"It was beautiful, quite and everything we expected!! Thanks for a great stay!!"
United States
Heather
The price is AU$212
includes taxes & fees
19 Feb - 20 Feb
Vallee Suite at Baetje Farms

Private Home, quiet neighborhood, So. IL, close to St. Louis

Private Home, quiet neighborhood, So. IL, close to St. Louis
Red Bud
10.0 out of 10, Exceptional, (23 reviews)
"Such a great place to stay. This house is so clean, well furnished, and beautiful."
United States
zach a.
The price is AU$446
includes taxes & fees
31 Jan - 1 Feb
Private Home, quiet neighborhood, So. IL, close to St. Louis

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, (8 reviews)
"Do yourself a favor and book this property. We have booked many properties all over Illinois and Missouri and this place just jumped to the top of our list. The property is so relaxing in countless ways. Very secluded, yet restaurants and everything you need are just 15 minutes away in Waterloo."
United States
Jeff
The price is AU$373
includes taxes & fees
24 Jan - 25 Jan
In the Country a Beautiful 2-bedroom house with its own private lake
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

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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 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?

Secluded Lodge with Private Lake Minutes from St. Louis: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What can I see and do in Chester?

Elzie C. Segar Memorial Park and Mississippi River 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 Mary's River Covered Bridge.

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.