Chester Holiday Rentals

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Chester holiday rentals

View from property

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
2.0 star property
French Village
9.8 out of 10, Exceptional, (58 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is HK$659
HK$1,047 total
includes taxes & fees
15 Apr - 16 Apr
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Terrace/patio

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (5 reviews)
"Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing "
United States
Chris
The price is HK$485
HK$1,130 total
includes taxes & fees
13 Apr - 14 Apr
Tiny Houses of French Village
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (276 reviews)
"It was the perfect spot for a weekend getaway!"
United States
Brittany P.
The price is HK$1,159
HK$1,404 total
includes taxes & fees
13 Apr - 14 Apr
Beautiful Modern Loft In Wine Country!
Property grounds

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (21 reviews)
"Couple that owned property very and welcoming. Bed was very comfortable and was nice."
United States
Julie
The price is HK$529
HK$727 total
includes taxes & fees
14 Apr - 15 Apr
Countryside Private Guest Room
Dining

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Ste. Genevieve
10.0 out of 10, Exceptional, (24 reviews)
"Great historic property!"
United States
Rhonda R.
The price is HK$917
HK$1,809 total
includes taxes & fees
21 Apr - 22 Apr
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Interior

Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4
Ste.Genevieve
10.0 out of 10, Exceptional, (61 reviews)
"This was my second stay. It's a cute place and very clean. The owners are great with communication. I highly recommend staying here. "
United States
Randy
The price is HK$782
HK$1,658 total
includes taxes & fees
12 Apr - 13 Apr
Cozy Haven Little Hidden Gem Sleeps 4
Interior

Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (4 reviews)
"It was beautiful, quite and everything we expected!! Thanks for a great stay!!"
United States
Heather
The price is HK$744
HK$1,097 total
includes taxes & fees
13 Apr - 14 Apr
Vallee Suite at Baetje Farms
Room

June Bug's Loft

June Bug's Loft
Perryville
10.0 out of 10, Exceptional, (8 reviews)
"Really enjoyed this place right in the heart of it all very easy to walk the town from here will be staying again for sure loved it"
United States
Jacqueline H.
The price is HK$705
HK$922 total
includes taxes & fees
11 Apr - 12 Apr
June Bug's Loft
Smart TV

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

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Oraville
10.0 out of 10, Exceptional, (4 reviews)
"Very nice place, will definitely be back."
United States
Greg W.
The price is HK$1,058
HK$1,876 total
includes taxes & fees
22 Apr - 23 Apr
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Property grounds

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (72 reviews)
"Great place to stay!"
United States
Lettitia B.
The price is HK$1,034
HK$1,462 total
includes taxes & fees
27 Apr - 28 Apr
"Little Brick House on Main (1865)”
Exterior

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

In the Country a Beautiful 2-bedroom house with its own private lake
Waterloo
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful setting, comfortable beds and host was very accommodating."
United States
Karla M.
The price is HK$1,234
HK$1,930 total
includes taxes & fees
23 Apr - 24 Apr
In the Country a Beautiful 2-bedroom house with its own private lake
Terrace/patio

Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$783
HK$1,136 total
includes taxes & fees
15 Apr - 16 Apr
Coeur de la Crème Suite at Baetje Farms
Interior

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
The price is HK$641
HK$1,309 total
includes taxes & fees
21 Apr - 22 Apr
The Atrium - A Boutique Hotel
Interior

Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing
French Village
9.0 out of 10, Wonderful, (4 reviews)
"Property was beautiful. Had a issue with house not being cleaned yet when we checked in, but we were immediately set up in house next door that was cleaned and ready for rental. "
United States
KIM N.
The price is HK$501
HK$1,191 total
includes taxes & fees
13 Apr - 14 Apr
Tiny Houses of French Village Tranquil & Relaxing
Exterior detail

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (45 reviews)
"Clean great place for me and my dog "
United States
Trey A.
The price is HK$1,175
HK$1,411 total
includes taxes & fees
30 Apr - 1 May
Sweet Farm Stay
Exterior

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Bloomsdale
10.0 out of 10, Exceptional, (13 reviews)
"Nice house to have a small Christmas get together with great hosts."
United States
Sean D.
The price is HK$1,410
HK$2,158 total
includes taxes & fees
15 Apr - 16 Apr
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Outdoor spa tub

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (29 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is HK$1,253
HK$2,166 total
includes taxes & fees
13 Apr - 14 Apr
Homestead Hideaway + Hot Tub
Property grounds

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (72 reviews)
"Awesome, clean house in a nice little town. We had all we needed and host was so easy to communicate with. We would definitely return!"
United States
PATRICK E.
The price is HK$1,175
HK$1,868 total
includes taxes & fees
26 Apr - 27 Apr
Peter Ray House
4 bedrooms, desk, free WiFi, bed sheets

Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.

Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.
Saint Mary
9.8 out of 10, Exceptional, (8 reviews)
"Large space which was great. Big bedrooms. "
United States
Robin
The price is HK$1,100
HK$3,124 total
includes taxes & fees
29 Apr - 30 Apr
Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.
Full-sized fridge, microwave, oven, stovetop

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.2 out of 10, Wonderful, (17 reviews)
"Great place to stay! "
United States
Eric
The price is HK$1,516
HK$2,361 total
includes taxes & fees
14 Apr - 15 Apr
Urban Lofts
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

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Cozy and most of all very accomodating staff. The best stay.. there is no one like it. (No exaggeration)"
Felix Oliver 1-night trip
Posted 12 hours ago
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
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  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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 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.