Holiday Rentals in Chester

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Holiday Rentals in Chester

Cabin in Belleville

10.0 out of 10, Exceptional, (94)
"Great place to stay. Highly recommend. "
United States
Christopher B.
Private Cabin with Pond on Family Farm

Holiday Home in Ste. Genevieve

10.0 out of 10, Exceptional, (62)
"Great place to stay!"
United States
Lettitia B.
The price is €142
includes taxes & fees
24 Nov - 25 Nov
"Little Brick House on Main (1865)”

Holiday Home in Millstadt

10.0 out of 10, Exceptional, (211)
"House and property were awesome house was stocked with plenty of seasonings pots an pans for cooking fishing there was good owners of property were awesome people "
United States
Marcus H.
Secluded Lodge with Private Lake Minutes from St. Louis

Holiday Home in Waterloo

10.0 out of 10, Exceptional, (5)
The price is €225
includes taxes & fees
25 Nov - 26 Nov
In the Country a Beautiful 2-bedroom house with its own private lake

Holiday Home in New Offenburg

10.0 out of 10, Exceptional, (4)
"Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. "
United States
Tim M.
The price is €268
includes taxes & fees
24 Nov - 25 Nov
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Holiday Home in Ste. Genevieve

10.0 out of 10, Exceptional, (54)
"Great place. Close to everything you need for a great stay in St. Genevieve. Easy check and great host."
United States
Justin S.
The price is €241
includes taxes & fees
25 Nov - 26 Nov
Doves Nest Guest House<br> Tranquil & Relaxing

Apartment in Ste. Genevieve

10.0 out of 10, Exceptional, (270)
"Loved our stay here! Thoughtful amenities on a beautiful property. Great communication with host. "
United States
Elsie H.
The price is €160
includes taxes & fees
25 Nov - 26 Nov
Beautiful Modern Loft In Wine Country!

Cabin in Ste. Genevieve

10.0 out of 10, Exceptional, (58)
"Beautiful tranquil and very roomy !! Perfect place to stay !!"
United States
geri b.
The price is €322
includes taxes & fees
24 Nov - 25 Nov
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Holiday Home in Ste. Genevieve

10.0 out of 10, Exceptional, (136)
"It’s perfect and already booking next year!"
United States
Joan H.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Holiday Home in Ste. Genevieve

9.8 out of 10, Exceptional, (20)
"This was a very nice house in an excellent location! Very easy to walk to historic downtown area. They had all the amenities we would need. "
United States
Lindsay W.
Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town

Holiday Home in Maeystown

10.0 out of 10, Exceptional, (70)
"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 €197
includes taxes & fees
24 Nov - 25 Nov
Peter Ray House

Cabin in Perryville

9.8 out of 10, Exceptional, (8)
"We enjoyed our stay! Peaceful and relaxing.John and Bambi"
United States
Bambi and John B.
Hot Tub & Creek Views: Secluded Perryville Cabin

Cabin in Ste. Genevieve

10.0 out of 10, Exceptional, (5)
"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."
United States
Deborah J.
The price is €228
includes taxes & fees
26 Nov - 27 Nov
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

Cabin in Perryville

2.0 star property
10.0 out of 10, Exceptional, (5)
"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. "
United States
joel r.
The price is €392
includes taxes & fees
30 Nov - 1 Dec
TreeLoft at BaseCamp

Holiday Home in Ste.Genevieve

9.8 out of 10, Exceptional, (53)
"Super cute cottage! Very clean. Quick walk to town. We thoroughly enjoyed our stay here. "
United States
Marianne A.
Cozy Haven Little Hidden Gem Sleeps 4

Holiday Home in Bloomsdale

10.0 out of 10, Exceptional, (6)
"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! "
United States
Blake H.
The price is €233
includes taxes & fees
13 Dec - 14 Dec
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Holiday Home in Ste. Genevieve

10.0 out of 10, Exceptional, (175)
"Great property and enjoyed our stay! Thank you!!"
United States
Sheila D.
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Apartment in Murphysboro

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. "
United States
Ross
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Holiday Home in Fults

10.0 out of 10, Exceptional, (27)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is €219
includes taxes & fees
1 Dec - 2 Dec
Homestead Hideaway + Hot Tub

Holiday Home in Ste. Genevieve

10.0 out of 10, Exceptional, (78)
"Best house we've had by far for our annual trip. "
United States
Nikolay P.
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
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, apart-hotels, 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 €121 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 Kaskaskia Bell 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.