Chester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Chester vacation 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, (48 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is ￥14,395
￥22,080 total
includes taxes & fees
Feb 1 - Feb 2
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
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 ￥19,158
￥37,308 total
includes taxes & fees
Feb 8 - Feb 9
Peaceful Country Home
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 ￥10,338
￥14,204 total
includes taxes & fees
Feb 1 - Feb 2
Countryside Private Guest Room
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 ￥18,377
￥34,732 total
includes taxes & fees
Jan 31 - Feb 1
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
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 ￥19,908
￥30,838 total
includes taxes & fees
Jan 31 - Feb 1
Fit and Fueled Studio
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, (21 reviews)
"Great historic property!"
United States
Rhonda R.
The price is ￥17,917
￥31,853 total
includes taxes & fees
Jan 31 - Feb 1
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Property grounds

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (71 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 ￥20,674
￥33,758 total
includes taxes & fees
Jan 31 - Feb 1
Peter Ray House
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (272 reviews)
"It was the perfect place to stay for a wedding in St. Gen. The place was very clean and we had an easy check in process!"
United States
Haley G.
The price is ￥22,665
￥27,518 total
includes taxes & fees
Feb 1 - Feb 2
Beautiful Modern Loft In Wine Country!
Microwave, oven, stovetop

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
The price is ￥15,927
￥26,618 total
includes taxes & fees
Feb 2 - Feb 3
Fishing Cabin next to Kinkaid Lake
Full-size 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
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 ￥14,548
￥21,439 total
includes taxes & fees
Feb 2 - Feb 3
Vallee Suite at Baetje Farms
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 ￥15,314
￥22,205 total
includes taxes & fees
Feb 1 - Feb 2
Coeur de la Crème Suite at Baetje Farms
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 ￥21,440
￥39,439 total
includes taxes & fees
Feb 9 - Feb 10
Homestead Hideaway + Hot Tub
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 ￥23,277
￥53,557 total
includes taxes & fees
Feb 9 - Feb 10
New Charming 2-bedroom cottage with Patio in Downtown Waterloo
Property grounds

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (65 reviews)
"Great place to stay!"
United States
Lettitia B.
The price is ￥18,193
￥24,319 total
includes taxes & fees
Feb 3 - Feb 4
"Little Brick House on Main (1865)”
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 ￥22,743
￥41,470 total
includes taxes & fees
Feb 1 - Feb 2
Farmstead home w/hot tub
Outdoor spa tub

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

Retreat Air - King Bed, Hot Tub & No cleaning fee
Perryville
The price is ￥20,675
￥23,738 total
includes taxes & fees
Jan 31 - Feb 1
Retreat Air - King Bed, Hot Tub & No cleaning fee
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 ￥31,013
￥46,826 total
includes taxes & fees
Jan 31 - Feb 1
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 ￥22,665
￥53,233 total
includes taxes & fees
Feb 1 - Feb 2
NEW! Speakeasy Cottage
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

Days Inn by Wyndham Perryville

Days Inn by Wyndham Perryville

10/10 Excellent
"Great people there"
Trasea 1-night trip
Posted 22 hours ago
Days Inn by Wyndham Perryville

Find out more about Chester

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

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?

"Little Brick House on Main (1865)”: This vacation home rental outside of Chester offers a patio, a private yard, 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 Cohen Memorial Home.

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.