A steel bridge over a river with a white boat.

Chester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (80 reviews)
"The Experience was amazing and we enjoyed the views and the firepit!"
United States
Kenzia
The price is NZ$282
includes taxes & fees
13 July - 14 July
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.6 out of 10, Exceptional, (4 reviews)
"What an amazing little suite wrapped in a very thought-filled overall venue. Very unique room with a so many details. The overall building with fire pit, game rooms, and local vendor items…all was quite amazing. Every element is thought out very well. It is very convenient and overall comfortable. It was a great getaway."
United States
Brian
The price is NZ$272
includes taxes & fees
2 Aug - 3 Aug
The Atrium - A Boutique Hotel

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (5 reviews)
"Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing "
United States
Chris
The price is NZ$597
includes taxes & fees
6 July - 7 July
Tiny Houses of French Village

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.4 out of 10, Exceptional, (22 reviews)
"Family of 4 with young kids. Wonderful host, immaculately kept property and right next door to a great food/drinks joint. We were impressed and would return without hesitation."
United States
Amar
The price is NZ$548
includes taxes & fees
5 July - 6 July
Urban Lofts

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (284 reviews)
"Clean and spacious but hard to find location "
United States
William
The price is NZ$335
includes taxes & fees
10 July - 11 July
Beautiful Modern Loft In Wine Country!

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, (59 reviews)
"Very charming log cabin perfect for a girls’ weekend close to the winery very clean property easy to reach the host. This is my third stay here and I would definitely stay again."
United States
Cheryl B.
The price is NZ$686
includes taxes & fees
15 July - 16 July
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (73 reviews)
"Awesome, clean house in a nice little town. We had all we needed and host was so easy to communicate with. We would definitely return!"
United States
PATRICK E.
The price is NZ$388
includes taxes & fees
8 July - 9 July
Peter Ray House

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (46 reviews)
The price is NZ$317
includes taxes & fees
13 July - 14 July
Sweet Farm Stay

Cozy 2-bedroom cottage in charming Ste. Genevieve

Cozy 2-bedroom cottage in charming Ste. Genevieve
Ste. Genevieve
10.0 out of 10, Exceptional, (1 review)
"We enjoyed a peaceful stay at the little brick house. Julie was a great host. We would love to stay again when we are in the area."
United States
Mindy S.
The price is NZ$325
includes taxes & fees
5 July - 6 July
Cozy 2-bedroom cottage in charming Ste. Genevieve

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, (10 reviews)
"Great communication great stay everything was perfect."
United States
Beauncka G.
The price is NZ$487
includes taxes & fees
7 July - 8 July
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

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

Retreat Air - King Bed, Hot Tub & No cleaning fee
Perryville
10.0 out of 10, Exceptional, (7 reviews)
"Great host. Would stay again."
United States
Chris E.
The price is NZ$303
includes taxes & fees
3 July - 4 July
Retreat Air - King Bed, Hot Tub & No cleaning fee

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, (23 reviews)
"We loved everything about the property."
United States
Vince
The price is NZ$438
includes taxes & fees
8 July - 9 July
In the Country a Beautiful 2-bedroom house with its own private lake

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (25 reviews)
"Awesome place to stay really nice host would highly recommend!!!!"
United States
Cayson P.
The price is NZ$163
includes taxes & fees
6 July - 7 July
Countryside Private Guest Room

Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

Stay On Festus Main 2 bedroom 1.5 bath Near Mercy
Festus
10.0 out of 10, Exceptional, (1 review)
"Great property and location. Property was clean. Very convenient to local attractions. Communications with the host was fast and efficient. Will rent this property again in the future."
United States
Jennifer B.
The price is NZ$518
includes taxes & fees
5 July - 6 July
Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Ste. Genevieve
10.0 out of 10, Exceptional, (3 reviews)
"5 Charles Farms was the perfect location to stay following a wedding at Charleville Brewery & Winery. Everything was clean and tidy, and the snacks were a great bonus! Would definitely stay here again if coming to the area."
United States
Nicole T.
The price is NZ$417
includes taxes & fees
6 July - 7 July
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
10.0 out of 10, Exceptional, (1 review)
"Cabin was fine. Beds were good, kitchen was clean. Rooms were clean also. The hosts provided excellent extras that made a big difference. Toilets worked just fine. Since we were both in our 70s we found it tough to sit as they were quite low and seemed small. Grill was ok. Could use a burner cover on one of the burners but that did not affect our use.Overall it was a very good cabin. A fishing cabin!Picnic table outside was rotted and one section gave way when my partner rested his elbows on it....
United States
thomas s.
The price is NZ$448
includes taxes & fees
6 July - 7 July
Fishing Cabin next to Kinkaid Lake

Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing
French Village
9.8 out of 10, Exceptional, (7 reviews)
"Loved it. Will rent again soon!"
United States
Sherri G.
The price is NZ$615
includes taxes & fees
6 July - 7 July
Tiny Houses of French Village Tranquil & Relaxing

Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (3 reviews)
"Spotless comfortable room"
United States
Barbara
The price is NZ$255
includes taxes & fees
5 July - 6 July
Coeur de la Crème Suite at Baetje Farms

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (49 reviews)
The price is NZ$516
includes taxes & fees
19 July - 20 July
Peaceful Country Home

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
New Offenburg
10.0 out of 10, Exceptional, (13 reviews)
"The host was very responsive, the house was spotless, and the beds were so comfortable. It was a lovely stay."
United States
Karen M.
The price is NZ$513
includes taxes & fees
6 July - 7 July
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$163 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 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?

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 Cohen Memorial Home.

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.