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, (61 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is AU$209
includes taxes & fees
27 Apr - 28 Apr
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, (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 AU$439
includes taxes & fees
28 Apr - 29 Apr
Tiny Houses of French Village

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
8.0 out of 10, Very good, (1 review)
"I like it but there is room for improvement on the little things. For a personal stay and non business it would be a little better. I have stayed twice for business. It’s clean but due to the openness it’s hard to control the temp in the room. My first stay the wifi didn’t work and cell reception is minimal so using phone as a hot spot was less than ideal. I like the kitchenette area and comes with everything you need but no area to use it. If you want to use the electric pan they have you can’t...
United States
Michael
The price is AU$220
includes taxes & fees
27 Apr - 28 Apr
The Atrium - A Boutique Hotel

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (278 reviews)
"It was a quiet little get away with great hospitality and beautiful scenery! "
United States
Karissa W.
The price is AU$253
includes taxes & fees
26 Apr - 27 Apr
Beautiful Modern Loft In Wine Country!

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (21 reviews)
"Awesome place to stay really nice host would highly recommend!!!!"
United States
Cayson P.
The price is AU$132
includes taxes & fees
4 May - 5 May
Countryside Private Guest Room

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

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Ste. Genevieve
10.0 out of 10, Exceptional, (24 reviews)
"Quiet, great location, clean, and comfortable."
United States
Gina C.
The price is AU$325
includes taxes & fees
28 Apr - 29 Apr
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

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

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Oraville
10.0 out of 10, Exceptional, (4 reviews)
"Very nice place, will definitely be back."
United States
Greg W.
The price is AU$378
includes taxes & fees
25 Apr - 26 Apr
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

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, (15 reviews)
"Beautiful setting, comfortable beds and host was very accommodating."
United States
Karla M.
The price is AU$348
includes taxes & fees
29 Apr - 30 Apr
In the Country a Beautiful 2-bedroom house with its own private lake

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (72 reviews)
"Great place to stay!"
United States
Lettitia B.
The price is AU$243
includes taxes & fees
4 May - 5 May
"Little Brick House on Main (1865)”

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$198
includes taxes & fees
24 May - 25 May
Vallee Suite at Baetje Farms

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (72 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 AU$310
includes taxes & fees
26 Apr - 27 Apr
Peter Ray House

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 AU$205
includes taxes & fees
24 May - 25 May
Coeur de la Crème Suite at Baetje Farms

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (45 reviews)
"Clean great place for me and my dog "
United States
Trey A.
The price is AU$254
includes taxes & fees
17 May - 18 May
Sweet Farm Stay

Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4
Ste.Genevieve
10.0 out of 10, Exceptional, (63 reviews)
"This was my second stay. It's a cute place and very clean. The owners are great with communication. I highly recommend staying here. "
United States
Randy
The price is AU$304
includes taxes & fees
6 May - 7 May
Cozy Haven Little Hidden Gem Sleeps 4

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Bloomsdale
10.0 out of 10, Exceptional, (14 reviews)
"Nice house to have a small Christmas get together with great hosts."
United States
Sean D.
The price is AU$386
includes taxes & fees
30 Apr - 1 May
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (29 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is AU$408
includes taxes & fees
11 May - 12 May
Homestead Hideaway + Hot Tub

Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.

Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.
Saint Mary
9.8 out of 10, Exceptional, (8 reviews)
"Large space which was great. Big bedrooms. "
United States
Robin
The price is AU$526
includes taxes & fees
29 Apr - 30 Apr
Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.

Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Oraville
The price is AU$173
includes taxes & fees
7 May - 8 May
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.2 out of 10, Wonderful, (18 reviews)
"Great place to stay! "
United States
Eric
The price is AU$428
includes taxes & fees
28 Apr - 29 Apr
Urban Lofts

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$287
includes taxes & fees
25 Apr - 26 Apr
Fit and Fueled Studio
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$209 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?

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.