Chester Holiday Rentals

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Holiday Rentals in Chester

Our top choices for Chester holiday rentals

Postcard Cabins St. Francois

2.0 star property
9.8 out of 10, Exceptional, (35)
"Peaceful, beautiful stay. "
The price is AU$202
includes taxes & fees
28 Sept - 29 Sept
Postcard Cabins St. Francois

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (265)
"My view was totally amazing. Very clean and roomy. Bed was very comfortable. Furnished very nice"
The price is AU$274
includes taxes & fees
28 Sept - 29 Sept
Beautiful Modern Loft In Wine Country!

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (88)
"Great weather great view great time was our 2nd stay going back again next fall "
Private Cabin with Pond on Family Farm

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (208)
"For a group of empty nesters, a girls trip has a different meaning than it does when you're in your 20s and 30s. This place gives you a chance to relax, let loose a little, get out of your comfort zone a little, fish, go kayaking, and spend some well deserved time together. "
Secluded Lodge with Private Lake Minutes from St. Louis

Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

10.0 out of 10, Exceptional, (120)
"The cabin was clean and cozy and perfect location to all the breweries and restaurants we wanted to check out. And loved that it was pet friendly since we love bringing our dog with us everywhere! Highly recommend! "
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

Doves Nest Guest House<br> Tranquil & Relaxing

10.0 out of 10, Exceptional, (46)
"Outstanding! I highly recommend to everyone! So well decorated with every amenity! Great location and easy walk to restaurants and activities and shopping! Great hosts!"
The price is AU$340
includes taxes & fees
6 Oct - 7 Oct
Doves Nest Guest House<br> Tranquil & Relaxing

Hot Tub & Creek Views: Secluded Perryville Cabin

9.6 out of 10, Exceptional, (4)
"We enjoyed our stay! Peaceful and relaxing.John and Bambi"
Hot Tub & Creek Views: Secluded Perryville Cabin

"Little Brick House on Main (1865)”

10.0 out of 10, Exceptional, (51)
"The property is a lovely little house, close to places to eat and attractions. "
The price is AU$244
includes taxes & fees
8 Oct - 9 Oct
"Little Brick House on Main (1865)”

⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4

2.0 star property
10.0 out of 10, Exceptional, (11)
"Amazing property super quiet and chill."
The price is AU$370
includes taxes & fees
1 Oct - 2 Oct
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4

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

10.0 out of 10, Exceptional, (76)
"What an unforgettable weekend! From the moment we arrived at Bauman's Deep Woods Escape, it was clear that every single detail had been thoughtfully curated for a perfect stay. This place truly lives up to its name—a serene, secluded retreat where relaxation reigns supreme. The amenities? Spot on and exactly as advertised—if not better. If you're dreaming of a peaceful getaway where you can unplug, unwind, and recharge, look no further. Bauman’s is the ultimate escape. We can’t wait to come...
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

3.0 star property
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. "
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

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

10.0 out of 10, Exceptional, (3)
"Tiny house was absolutely perfect for a quick getaway or even a longer stay had everything we needed except a toaster! Owners were great on getting in touch for anything needed."
The price is AU$392
includes taxes & fees
28 Sept - 29 Sept
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

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

10.0 out of 10, Exceptional, (168)
"Nice location, clean and inviting."
The price is AU$368
includes taxes & fees
1 Oct - 2 Oct
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

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

10.0 out of 10, Exceptional, (134)
"It’s perfect and already booking next year!"
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

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

The price is AU$386
includes taxes & fees
28 Sept - 29 Sept
In the Country a Beautiful 2-bedroom house with its own private lake

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

10.0 out of 10, Exceptional, (55)
"Wonderful place to stay in Ste Genevieve wine country"
The price is AU$553
includes taxes & fees
28 Sept - 29 Sept
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Urban Lofts

3.0 star property
9.2 out of 10, Wonderful, (17)
"Great place to stay! "
Urban Lofts

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

10.0 out of 10, Exceptional, (5)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
The price is AU$425
includes taxes & fees
28 Sept - 29 Sept
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

TreeLoft at BaseCamp

2.0 star property
10.0 out of 10, Exceptional, (4)
"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. "
The price is AU$755
includes taxes & fees
2 Oct - 3 Oct
TreeLoft at BaseCamp

Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing

10.0 out of 10, Exceptional, (28)
"Had everything we needed, nice home and vacay."
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
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

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$202 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?

Doves Nest Guest House
Tranquil & Relaxing
: This holiday home rental outside of Chester is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.