Chester Holiday Rentals

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Holiday Rentals in Chester

Vallee Suite at Baetje Farms

Bloomsdale
10.0 out of 10, Exceptional, (4)
"It was beautiful, quite and everything we expected!! Thanks for a great stay!!"
United States
Heather
The price is AU$218
includes taxes & fees
30 Nov - 1 Dec
Vallee Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms

Bloomsdale
10.0 out of 10, Exceptional, (2)
"It was super cozy and relaxed, the kind of place that makes you want to slow down and just hang out. Really warm vibe, almost like a little hidden getaway"
United States
Eric C.
The price is AU$226
includes taxes & fees
20 Nov - 21 Nov
Coeur de la Crème Suite at Baetje Farms

Tiny Houses of French Village

2.5 star property
French Village
10.0 out of 10, Exceptional, (3)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
United States
Norma
Tiny Houses of French Village

Countryside Private Guest Room

Freeburg
10.0 out of 10, Exceptional, (17)
"Owners were awesome and it was my first time staying in a B&B . I will never stay in another hotel when visiting StLouis . I was very impressed with the hospitality and location ."
United States
David B.
The price is AU$146
includes taxes & fees
25 Nov - 26 Nov
Countryside Private Guest Room

Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

Oraville
8.0 out of 10, Very good, (1)
"If used for hunting, maybe have a set up for cleaning of game ."
United States
john l.
The price is AU$312
includes taxes & fees
23 Nov - 24 Nov
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

Fit and Fueled Studio

Pinckneyville
10.0 out of 10, Exceptional, (1)
"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$321
includes taxes & fees
16 Dec - 17 Dec
Fit and Fueled Studio

Peter Ray House

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 AU$348
includes taxes & fees
21 Nov - 22 Nov
Peter Ray House

Peaceful Country Home

Marissa
10.0 out of 10, Exceptional, (48)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is AU$413
includes taxes & fees
25 Nov - 26 Nov
Peaceful Country Home

Beautiful Modern Loft In Wine Country!

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 AU$279
includes taxes & fees
25 Nov - 26 Nov
Beautiful Modern Loft In Wine Country!

"Little Brick House on Main (1865)”

Ste. Genevieve
10.0 out of 10, Exceptional, (62)
"Great place to stay!"
United States
Lettitia B.
The price is AU$247
includes taxes & fees
20 Nov - 21 Nov
"Little Brick House on Main (1865)”

Doves Nest Guest House<br> Tranquil & Relaxing

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 AU$416
includes taxes & fees
23 Nov - 24 Nov
Doves Nest Guest House<br> Tranquil & Relaxing

Homestead Hideaway + Hot Tub

Fults
10.0 out of 10, Exceptional, (27)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is AU$382
includes taxes & fees
1 Dec - 2 Dec
Homestead Hideaway + Hot Tub

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

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 AU$466
includes taxes & fees
20 Nov - 21 Nov
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

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

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 AU$431
includes taxes & fees
20 Nov - 21 Nov
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

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

2.0 star property
Oraville
10.0 out of 10, Exceptional, (3)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is AU$380
includes taxes & fees
19 Dec - 20 Dec
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

New Charming 2-bedroom cottage with Patio in Waterloo

Waterloo
The price is AU$541
includes taxes & fees
8 Dec - 9 Dec
New Charming 2-bedroom cottage with Patio in Waterloo

TreeLoft at BaseCamp

2.0 star property
Perryville
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 AU$701
includes taxes & fees
23 Nov - 24 Nov
TreeLoft at BaseCamp

Farmstead home w/hot tub

Marissa
10.0 out of 10, Exceptional, (14)
"Cozy country setting. We had everything we needed for our stay. The hosts made our it easy and enjoyable for our family of 7."
United States
Alan P.
The price is AU$431
includes taxes & fees
23 Nov - 24 Nov
Farmstead home w/hot tub

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

Ste. Genevieve
10.0 out of 10, Exceptional, (4)
"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 AU$399
includes taxes & fees
20 Nov - 21 Nov
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
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$213 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?

Cozy Haven Little Hidden Gem Sleeps 4: This holiday home rental outside of Chester is located in the city centre, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 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 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.