Chester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Chester

Living area
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
Exterior
Countryside Private Guest Room

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 HK$525
HK$721 total
includes taxes & fees
22 Nov - 23 Nov
Countryside Private Guest Room
Interior
Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms

Bloomsdale
10.0 out of 10, Exceptional, (4)
"Enjoyed the property. Very clean and accommodating. "
United States
Tracey E.
The price is HK$738
HK$1,088 total
includes taxes & fees
13 Nov - 14 Nov
Vallee Suite at Baetje Farms
Property grounds
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$1,112
HK$2,061 total
includes taxes & fees
25 Nov - 26 Nov
Peaceful Country Home
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

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 HK$894
HK$1,557 total
includes taxes & fees
13 Nov - 14 Nov
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

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$1,010
HK$1,606 total
includes taxes & fees
19 Nov - 20 Nov
Fit and Fueled Studio
Interior
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$777
HK$1,127 total
includes taxes & fees
17 Nov - 18 Nov
Coeur de la Crème Suite at Baetje Farms
Property grounds
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$1,049
HK$1,746 total
includes taxes & fees
14 Nov - 15 Nov
Peter Ray House
Exterior detail
"Little Brick House on Main (1865)”

"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 HK$756
HK$1,067 total
includes taxes & fees
13 Nov - 14 Nov
"Little Brick House on Main (1865)”
Exterior
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)
"Great property and great owners!!!!"
United States
Aaron M.
The price is HK$1,049
HK$1,911 total
includes taxes & fees
27 Nov - 28 Nov
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!

Ste. Genevieve
10.0 out of 10, Exceptional, (270)
"Beautiful loft on beautiful property!"
United States
Addison G.
The price is HK$1,150
HK$1,404 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Modern Loft In Wine Country!
Outdoor spa tub
Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub

Fults
10.0 out of 10, Exceptional, (27)
"We were having a family reunion in the area and this quiet, relaxing get away spot provided a clean and private country home for us to stay for the weekend."
United States
Carol F.
The price is HK$1,010
HK$1,862 total
includes taxes & fees
9 Dec - 10 Dec
Homestead Hideaway + Hot Tub
Fridge, microwave, oven, stovetop
New Charming 2-bedroom cottage with Patio in Waterloo

New Charming 2-bedroom cottage with Patio in Waterloo

Waterloo
The price is HK$1,205
HK$2,710 total
includes taxes & fees
20 Nov - 21 Nov
New Charming 2-bedroom cottage with Patio in Waterloo
Outdoor dining
Doves Nest Guest House<br> Tranquil & Relaxing

Doves Nest Guest House<br> Tranquil & Relaxing

Ste. Genevieve
10.0 out of 10, Exceptional, (53)
"We loved our time here! I got married this past Sunday and my bridesmaids and I stayed here before the wedding! It was absolutely perfect!"
United States
Terra L.
The price is HK$1,259
HK$2,083 total
includes taxes & fees
21 Nov - 22 Nov
Doves Nest Guest House<br> Tranquil & Relaxing
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.

New Offenburg
10.0 out of 10, Exceptional, (4)
"Very clean - host was easy to work with. "
United States
Jamie M.
The price is HK$1,166
HK$2,330 total
includes taxes & fees
13 Nov - 14 Nov
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Interior
Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant

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

Perryville
The price is HK$1,516
HK$2,463 total
includes taxes & fees
13 Nov - 14 Nov
Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant
Fridge, microwave, oven, stovetop
Farmstead home w/hot tub

Farmstead home w/hot tub

Marissa
10.0 out of 10, Exceptional, (14)
"Excellent stay! Clean, great location for World Shooting Complex and close to Sparta. Highly Recommend 🌟 "
United States
Natalie A.
The price is HK$1,154
HK$2,154 total
includes taxes & fees
17 Nov - 18 Nov
Farmstead home w/hot tub
Dining
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

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

Bloomsdale
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay. The home and property were absolutely beautiful and Julie went above and beyond to accommodate us. I can't wait to go back."
United States
Jennifer M.
The price is HK$1,399
HK$2,155 total
includes taxes & fees
13 Nov - 14 Nov
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Interior
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

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

Ste. Genevieve
10.0 out of 10, Exceptional, (4)
"This home looks exactly like the picture. It is so cute and soooo clean!!!! It was very convenient to the wedding venue I was in town for. Communication was top notch and to top it off, I lost my car key in the driveway, and they shipped it back to me. Highly recommend this property! "
United States
Sheree B.
The price is HK$1,532
HK$1,990 total
includes taxes & fees
16 Nov - 17 Nov
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Pool
Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing

French Village
9.6 out of 10, Exceptional, (5)
"This was a fantastic couples getaway. The host has thought of all the little details. The pool was great. And, there was lots to do in the area."
United States
Matt T.
The price is HK$1,158
HK$2,024 total
includes taxes & fees
13 Nov - 14 Nov
Tiny Houses of French Village Tranquil & Relaxing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

10/10 Excellent
" Very clean rooms, friendly staff"
Brad 2-night trip
Posted 3 days ago
Holiday Inn Express & Suites Perryville by IHG

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?

In the Country a Beautiful 2-bedroom house with its own private lake: This holiday home rental outside of Chester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 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.