A steel bridge over a river with a white boat.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chester vacation rentals

Interior

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.6 out of 10, Exceptional, (4 reviews)
"What an amazing little suite wrapped in a very thought-filled overall venue. Very unique room with a so many details. The overall building with fire pit, game rooms, and local vendor items…all was quite amazing. Every element is thought out very well. It is very convenient and overall comfortable. It was a great getaway."
United States
Brian
The price is SAR 288
SAR 604 total
includes taxes & fees
28 Jun - 29 Jun
The Atrium - A Boutique Hotel
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, (80 reviews)
"The Experience was amazing and we enjoyed the views and the firepit!"
United States
Kenzia
The price is SAR 409
SAR 602 total
includes taxes & fees
6 Jul - 7 Jul
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Property grounds

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (24 reviews)
"Awesome place to stay really nice host would highly recommend!!!!"
United States
Cayson P.
The price is SAR 253
SAR 348 total
includes taxes & fees
28 Jun - 29 Jun
Countryside Private Guest Room
Exterior

Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Oraville
10.0 out of 10, Exceptional, (1 review)
The price is SAR 357
SAR 458 total
includes taxes & fees
10 Jul - 11 Jul
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (283 reviews)
"Clean and spacious but hard to find location "
United States
William
The price is SAR 556
SAR 721 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful Modern Loft In Wine Country!
Exterior

5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana

5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
New Offenburg
The price is SAR 591
SAR 719 total
includes taxes & fees
29 Jun - 30 Jun
5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
Outdoor dining

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)
"Very charming log cabin perfect for a girls’ weekend close to the winery very clean property easy to reach the host. This is my third stay here and I would definitely stay again."
United States
Cheryl B.
The price is SAR 1,014
SAR 1,466 total
includes taxes & fees
8 Jul - 9 Jul
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Interior

Amoureux Suite at Baetje Farms

Amoureux Suite at Baetje Farms
Bloomsdale
The price is SAR 357
SAR 526 total
includes taxes & fees
5 Jul - 6 Jul
Amoureux Suite at Baetje Farms
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
9.0 out of 10, Wonderful, (2 reviews)
"Had a nice time. Loved staying in the camper. The host was very prompt when communicating. Would definitely stay again."
United States
Joseph S.
The price is SAR 413
SAR 720 total
includes taxes & fees
10 Jul - 11 Jul
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
Interior

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

Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques
Perryville
The price is SAR 507
SAR 798 total
includes taxes & fees
28 Jun - 29 Jun
Urban Loft #8 METALL · Downtown Urban Loft above Restaurants & Boutiques
Exterior

Cozy 2-bedroom cottage in charming Ste. Genevieve

Cozy 2-bedroom cottage in charming Ste. Genevieve
Ste. Genevieve
10.0 out of 10, Exceptional, (1 review)
"We enjoyed a peaceful stay at the little brick house. Julie was a great host. We would love to stay again when we are in the area."
United States
Mindy S.
The price is SAR 563
SAR 696 total
includes taxes & fees
29 Jun - 30 Jun
Cozy 2-bedroom cottage in charming Ste. Genevieve
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 SAR 357
SAR 526 total
includes taxes & fees
28 Jun - 29 Jun
Vallee Suite at Baetje Farms
Full-size fridge, microwave, oven, stovetop

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.4 out of 10, Exceptional, (22 reviews)
"Family of 4 with young kids. Wonderful host, immaculately kept property and right next door to a great food/drinks joint. We were impressed and would return without hesitation."
United States
Amar
The price is SAR 757
SAR 1,168 total
includes taxes & fees
20 Jul - 21 Jul
Urban Lofts
Property grounds

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (73 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 SAR 507
SAR 844 total
includes taxes & fees
28 Jun - 29 Jun
Peter Ray House
Interior

Downtown Urban Loft above Restaurants

Downtown Urban Loft above Restaurants
Perryville
The price is SAR 871
SAR 1,361 total
includes taxes & fees
8 Jul - 9 Jul
Downtown Urban Loft above Restaurants
Exterior detail

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (46 reviews)
"Place is a beautiful little farm set in the farmland with all the things needed for a great day."
United States
Clint M.
The price is SAR 563
SAR 677 total
includes taxes & fees
29 Jun - 30 Jun
Sweet Farm Stay
Property grounds

TreeLoft at BaseCamp

TreeLoft at BaseCamp
Perryville
10.0 out of 10, Exceptional, (5 reviews)
"This place is perfect if you want a private upscale experience that is immersed in natural beauty. The treehouse is luxurious and so comfortable. We loved every minute of our stay. "
United States
joel r.
TreeLoft at BaseCamp
Exterior

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
New Offenburg
10.0 out of 10, Exceptional, (13 reviews)
"The host was very responsive, the house was spotless, and the beds were so comfortable. It was a lovely stay."
United States
Karen M.
The price is SAR 581
SAR 1,168 total
includes taxes & fees
30 Jun - 1 Jul
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
Exterior

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Ste. Genevieve
10.0 out of 10, Exceptional, (3 reviews)
"5 Charles Farms was the perfect location to stay following a wedding at Charleville Brewery & Winery. Everything was clean and tidy, and the snacks were a great bonus! Would definitely stay here again if coming to the area."
United States
Nicole T.
The price is SAR 591
SAR 896 total
includes taxes & fees
28 Jun - 29 Jun
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Property grounds

New! Luxury Meets Nature - TreeRise at BaseCamp

New! Luxury Meets Nature - TreeRise at BaseCamp
Perryville
10.0 out of 10, Exceptional, (6 reviews)
"Had the best stay. Loved the cozy feel. Loved the hot tub right outside the bedroom. "
United States
Kathleen F.
The price is SAR 1,221
SAR 1,988 total
includes taxes & fees
5 Jul - 6 Jul
New! Luxury Meets Nature - TreeRise at BaseCamp
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

Baymont by Wyndham Festus

Baymont by Wyndham Festus

10/10 Excellent
"Easy parking, great breakfast"
Pamela 1-night trip
Posted 3 hours ago
Baymont by Wyndham Festus

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near top attractions in Chester, or you can choose a more secluded option if you're looking for relaxation. 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 vacation home rentals that Chester has to offer?

In the Country a Beautiful 2-bedroom house with its own private lake: This vacation 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 Mary's River Covered Bridge and Fort Kaskaskia.

What are vacation rentals like in Chester?

Vacation rentals are private accommodations you can stay in for a short or long stay in Chester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.