Chester Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

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, (49 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is HK$458
HK$830 total
includes taxes & fees
16 Feb - 17 Feb
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, (3 reviews)
"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
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
Urban Lofts
Outdoor spa tub

Retreat Air - King Bed, Hot Tub & No cleaning fee

Retreat Air - King Bed, Hot Tub & No cleaning fee
Perryville
10.0 out of 10, Exceptional, (1 review)
"Kimberly went out of her way to get a pastry and balloon for my husband’s birthday! Place was extremely clean! They provided everything even down to the Tyl in the bathroom "
United States
Jennifer G.
The price is HK$1,094
HK$1,251 total
includes taxes & fees
13 Mar - 14 Mar
Retreat Air - King Bed, Hot Tub & No cleaning fee
Property grounds

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is HK$528
HK$725 total
includes taxes & fees
15 Feb - 16 Feb
Countryside Private Guest Room
Exterior detail

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (43 reviews)
"We had a very pleasant stay"
United States
Kate
The price is HK$1,172
HK$1,408 total
includes taxes & fees
1 Mar - 2 Mar
Sweet Farm Stay
Outdoor spa tub

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is HK$1,133
HK$2,054 total
includes taxes & fees
17 Feb - 18 Feb
Homestead Hideaway + Hot Tub
2 bedrooms, desk, bed sheets

Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
10.0 out of 10, Exceptional, (1 review)
"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$1,016
HK$1,607 total
includes taxes & fees
13 Feb - 14 Feb
Fit and Fueled Studio
Property grounds

Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl

Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl
Waterloo
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful stay! Loved your place!!!"
United States
Sandy G.
Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl
Property grounds

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (48 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is HK$978
HK$1,787 total
includes taxes & fees
16 Feb - 17 Feb
Peaceful Country Home
Interior

Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant

Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant
Perryville
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!"
United States
Thor L.
The price is HK$1,524
HK$2,477 total
includes taxes & fees
25 Feb - 26 Feb
Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant
Fridge, microwave, oven, stovetop

Private Home, quiet neighborhood, So. IL, close to St. Louis

Private Home, quiet neighborhood, So. IL, close to St. Louis
Red Bud
10.0 out of 10, Exceptional, (23 reviews)
"Such a great place to stay. This house is so clean, well furnished, and beautiful."
United States
zach a.
The price is HK$1,759
HK$2,610 total
includes taxes & fees
28 Feb - 1 Mar
Private Home, quiet neighborhood, So. IL, close to St. Louis
Private kitchen

NEW! Speakeasy Cottage

NEW! Speakeasy Cottage
Waterloo
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Spacious, decor wonderful,Convenient to restaurants and coffee cafes The owner was easy to communicate with and hands on We were snowed in and she helped us in every way Look forward to a return visit "
United States
Thomas L.
The price is HK$1,157
HK$2,693 total
includes taxes & fees
18 Feb - 19 Feb
NEW! Speakeasy Cottage
Dining

New Charming 2-bedroom cottage with Patio in Downtown Waterloo

New Charming 2-bedroom cottage with Patio in Downtown Waterloo
Waterloo
The price is HK$1,188
HK$2,693 total
includes taxes & fees
1 Mar - 2 Mar
New Charming 2-bedroom cottage with Patio in Downtown Waterloo
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, (8 reviews)
"Beautiful setting, comfortable beds and host was very accommodating."
United States
Karla M.
The price is HK$1,231
HK$1,967 total
includes taxes & fees
17 Feb - 18 Feb
In the Country a Beautiful 2-bedroom house with its own private lake
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, (3 reviews)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is HK$977
HK$1,823 total
includes taxes & fees
21 Feb - 22 Feb
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Property grounds

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (72 reviews)
"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$1,172
HK$1,856 total
includes taxes & fees
11 Mar - 12 Mar
Peter Ray House
Smart TV, fireplace

Farmstead home w/hot tub

Farmstead home w/hot tub
Marissa
10.0 out of 10, Exceptional, (15 reviews)
"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$1,161
HK$2,117 total
includes taxes & fees
15 Feb - 16 Feb
Farmstead home w/hot tub
Private kitchen

Gorgeous, downtown house!

Gorgeous, downtown house!
Perryville
10.0 out of 10, Exceptional, (1 review)
"Our stay was excellent and our host Carisa was a Great person to work with. The house was beautiful. The house worked out great for us. We had 6 people staying and we all had very comfortable beds and our own bathrooms. Great for a large family. "
United States
Doyle or Cheryl D.
The price is HK$3,986
HK$6,841 total
includes taxes & fees
24 Feb - 25 Feb
Gorgeous, downtown house!
Outdoor spa tub

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Ste. Genevieve
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful tranquil and very roomy !! Perfect place to stay !!"
United States
geri b.
The price is HK$2,110
HK$2,845 total
includes taxes & fees
15 Feb - 16 Feb
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
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
"Absolutely perfect stay! Beautiful clean cabin, fantastic views, so private and lovely. The amenities were great, and from beginning to end our stay was everything we wanted. "
Elisabeth 1-night trip
Posted 11 days 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?

"Little Brick House on Main (1865)”: This holiday home rental outside of Chester offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Chester?

Elzie C. Segar Memorial Park and Mississippi River 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 Kaskaskia Bell.

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.