Chester Holiday Rentals

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Holiday Rentals in Chester

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (89)
"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

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (265)
"Beautiful loft on beautiful property!"
The price is NZ$308
includes taxes & fees
5 Oct - 6 Oct
Beautiful Modern Loft In Wine Country!

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

The price is NZ$434
includes taxes & fees
3 Oct - 4 Oct
In the Country a Beautiful 2-bedroom house with its own private lake

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

Doves Nest Guest House<br> Tranquil & Relaxing

10.0 out of 10, Exceptional, (47)
"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 NZ$383
includes taxes & fees
6 Oct - 7 Oct
Doves Nest Guest House<br> Tranquil & Relaxing

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

2.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing property super quiet and chill."
The price is NZ$413
includes taxes & fees
2 Oct - 3 Oct
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4

"Little Brick House on Main (1865)”

10.0 out of 10, Exceptional, (52)
"The property is a lovely little house, close to places to eat and attractions. "
The price is NZ$274
includes taxes & fees
2 Oct - 3 Oct
"Little Brick House on Main (1865)”

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 NZ$442
includes taxes & fees
5 Oct - 6 Oct
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

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

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

10.0 out of 10, Exceptional, (76)
"Fully stocked. Had everything we could ever want. Very clean and comfortable."
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

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 NZ$416
includes taxes & fees
8 Oct - 9 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

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 NZ$628
includes taxes & fees
6 Oct - 7 Oct
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

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 NZ$482
includes taxes & fees
2 Oct - 3 Oct
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Urban Lofts

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

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!

Homestead Hideaway + Hot Tub

10.0 out of 10, Exceptional, (27)
"The residence was lovely in that it was just “away” from everything. We stayed in, cooked meals, played board games, enjoyed the hot tub and took in some movies. A lovely place to just get away. "
The price is NZ$446
includes taxes & fees
28 Oct - 29 Oct
Homestead Hideaway + Hot Tub

Ste. Genevieve Co. House w/ HOT TUB!

9.8 out of 10, Exceptional, (7)
"Large space which was great. Big bedrooms. "
Ste. Genevieve Co. House w/ HOT TUB!

Luxury 3BR Cottage, King Beds, Spa-Style Baths and Outdoor Oasis

10.0 out of 10, Exceptional, (2)
"This is such a cute, comfortable property. Nearby the courthouse with a lot of things to do within walking distance. Safe and clean town! The host was very thoughtful and puts sweet things out for her guests.. like fresh flowers, berries, and eggs! Would love to go back! Highly recommend visiting this home and town! Lots of unique history!! "
Luxury 3BR Cottage, King Beds, Spa-Style Baths and Outdoor Oasis
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 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$274 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 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.