Chester Holiday Rentals

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Our top choices for Chester holiday rentals

9.8 out of 10, Exceptional, (46)
"The cabin was cozy and very peaceful such a good experience "
United States
Russhell
The price is NZ$215
includes taxes & fees
5 Jan - 6 Jan
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Mobile Home in Bloomsdale

Vallee Suite at Baetje Farms
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 NZ$242
includes taxes & fees
4 Jan - 5 Jan
Vallee Suite at Baetje Farms

Holiday Home in Freeburg

Countryside Private Guest Room
10.0 out of 10, Exceptional, (17)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is NZ$160
includes taxes & fees
2 Jan - 3 Jan
Countryside Private Guest Room
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 NZ$250
includes taxes & fees
5 Jan - 6 Jan
Coeur de la Crème Suite at Baetje Farms
10.0 out of 10, Exceptional, (18)
"Great historic property!"
United States
Rhonda R.
The price is NZ$357
includes taxes & fees
14 Jan - 15 Jan
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

Holiday Home in French Village

Tiny Houses of French Village
2.5 star property
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
9.0 out of 10, Wonderful, (2)
"If used for hunting, maybe have a set up for cleaning of game ."
United States
john l.
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

Holiday Home in Pinckneyville

Fit and Fueled Studio
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 NZ$348
includes taxes & fees
2 Jan - 3 Jan
Fit and Fueled Studio
The price is NZ$302
includes taxes & fees
2 Jan - 3 Jan
Fishing Cabin next to Kinkaid Lake
10.0 out of 10, Exceptional, (3)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is NZ$395
includes taxes & fees
2 Jan - 3 Jan
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

Holiday Home in Maeystown

Peter Ray House
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 NZ$386
includes taxes & fees
2 Jan - 3 Jan
Peter Ray House

Apartment in Ste. Genevieve

Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, (271)
"It appeared to be. We never cooked anything during our stay. The host were very friendly and helpful during our stay. It is a beautiful place that is nice and relaxing. "
United States
stephanie b.
The price is NZ$310
includes taxes & fees
5 Jan - 6 Jan
Beautiful Modern Loft In Wine Country!

Holiday Home in Ste. Genevieve

"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (63)
"Great place to stay!"
United States
Lettitia B.
The price is NZ$274
includes taxes & fees
3 Jan - 4 Jan
"Little Brick House on Main (1865)”

Holiday Home in Marissa

Peaceful Country Home
10.0 out of 10, Exceptional, (48)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is NZ$457
includes taxes & fees
12 Jan - 13 Jan
Peaceful Country Home
10.0 out of 10, Exceptional, (9)
"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 NZ$479
includes taxes & fees
20 Jan - 21 Jan
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Holiday Home in Fults

Homestead Hideaway + Hot Tub
10.0 out of 10, Exceptional, (28)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is NZ$425
includes taxes & fees
5 Jan - 6 Jan
Homestead Hideaway + Hot Tub
10.0 out of 10, Exceptional, (7)
"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 NZ$521
includes taxes & fees
5 Jan - 6 Jan
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
The price is NZ$367
includes taxes & fees
2 Jan - 3 Jan
Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques
The price is NZ$628
includes taxes & fees
4 Jan - 5 Jan
New Charming 2-bedroom cottage with Patio in Waterloo

Holiday Home in Marissa

Farmstead home w/hot tub
10.0 out of 10, Exceptional, (15)
"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 NZ$479
includes taxes & fees
4 Jan - 5 Jan
Farmstead home w/hot tub
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 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$160 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 Randolph County State Recreation Area.

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.