Chester Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Chester holiday rentals

Private kitchen
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

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, (46)
"The cabin was cozy and very peaceful such a good experience "
United States
Russhell
The price is HK$589
HK$970 total
includes taxes & fees
13 Jan - 14 Jan
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Interior
Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms

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 HK$740
HK$1,090 total
includes taxes & fees
7 Jan - 8 Jan
Vallee Suite at Baetje Farms
Exterior
Countryside Private Guest Room

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (17)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is HK$526
HK$723 total
includes taxes & fees
4 Jan - 5 Jan
Countryside Private Guest Room
Interior
Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème 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 HK$779
HK$1,129 total
includes taxes & fees
13 Jan - 14 Jan
Coeur de la Crème Suite at Baetje Farms
Fridge, microwave, oven, stovetop
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

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

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
2.0 star property
Ste. Genevieve
10.0 out of 10, Exceptional, (18)
"Great historic property!"
United States
Rhonda R.
The price is HK$877
HK$1,601 total
includes taxes & fees
14 Jan - 15 Jan
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Living area
Tiny Houses of French Village

Tiny Houses of French Village

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
Fridge, microwave, oven, stovetop
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

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

Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
Oraville
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
Fridge, microwave, oven, stovetop
Fit and Fueled Studio

Fit and Fueled Studio

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 HK$1,013
HK$1,577 total
includes taxes & fees
4 Jan - 5 Jan
Fit and Fueled Studio
Property grounds
Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
The price is HK$810
HK$1,353 total
includes taxes & fees
16 Jan - 17 Jan
Fishing Cabin next to Kinkaid Lake
Exterior
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

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

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 HK$934
HK$1,741 total
includes taxes & fees
4 Jan - 5 Jan
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Property grounds
Peter Ray House

Peter Ray House

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 HK$1,051
HK$1,741 total
includes taxes & fees
14 Jan - 15 Jan
Peter Ray House
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
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 HK$1,152
HK$1,399 total
includes taxes & fees
11 Jan - 12 Jan
Beautiful Modern Loft In Wine Country!
Exterior detail
"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (63)
"Great place to stay!"
United States
Lettitia B.
The price is HK$925
HK$1,236 total
includes taxes & fees
11 Jan - 12 Jan
"Little Brick House on Main (1865)”
Property grounds
Peaceful Country Home

Peaceful Country Home

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 HK$1,114
HK$2,048 total
includes taxes & fees
13 Jan - 14 Jan
Peaceful Country Home
Dining
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.

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Bloomsdale
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 HK$1,402
HK$2,159 total
includes taxes & fees
11 Jan - 12 Jan
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

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is HK$1,051
HK$1,972 total
includes taxes & fees
26 Jan - 27 Jan
Homestead Hideaway + Hot Tub
Fridge, microwave, oven, stovetop
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

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

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
New Offenburg
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 HK$1,080
HK$2,224 total
includes taxes & fees
17 Jan - 18 Jan
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Interior
Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques

Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques

Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques
2.0 star property
Perryville
The price is HK$1,052
HK$1,657 total
includes taxes & fees
4 Jan - 5 Jan
Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques
Fridge, microwave, oven, stovetop
New Charming 2-bedroom cottage with Patio in Waterloo

New Charming 2-bedroom cottage with Patio in Waterloo

New Charming 2-bedroom cottage with Patio in Waterloo
Waterloo
The price is HK$1,247
HK$2,832 total
includes taxes & fees
4 Jan - 5 Jan
New Charming 2-bedroom cottage with Patio in Waterloo
Fridge, microwave, oven, stovetop
Farmstead home w/hot tub

Farmstead home w/hot tub

Farmstead home w/hot tub
Marissa
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 HK$1,157
HK$2,159 total
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

Super 8 by Wyndham Okawville

Super 8 by Wyndham Okawville

10/10 Excellent
"Yes"
Ricky 1-night trip
Posted 5 hours ago
Super 8 by Wyndham Okawville

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
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • 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 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.