Chester Vacation Rentals

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Vacation Rentals in Chester

Private Cabin with Pond on Family Farm

Belleville
10.0 out of 10, Exceptional, (93)
"The cabin is the perfect place to visit with our family. Quiet location on an orchard. Cabin is fully equipped for multi - day visits. Tom Range is a wonderful host."
United States
Charlie O.
Private Cabin with Pond on Family Farm

"Little Brick House on Main (1865)”

Ste. Genevieve
10.0 out of 10, Exceptional, (60)
"Great place to stay!"
United States
Lettitia B.
$146 nightly
The price is $146
Nov 11 - Nov 12
Total with taxes and fees
"Little Brick House on Main (1865)”

Cozy Haven Little Hidden Gem Sleeps 4

Ste.Genevieve
9.8 out of 10, Exceptional, (51)
"Great host and a cozy place to stay "
United States
Ashlynn P.
Cozy Haven Little Hidden Gem Sleeps 4

In the Country a Beautiful 2-bedroom house with its own private lake

Waterloo
10.0 out of 10, Exceptional, (4)
"We loved everything about our stay in the woods. From the minute we pulled into the secluded tree-lined driveway, we felt like we were truly in the woods. Megan, the host, was very kind and easy to communicate with. The house was well appointed and clean. The lake was AMAZING. The fall leaves made the place look magical. We fished, we hiked around the property and we played games in the shed that we brought from home. We will stay again. What a beautiful property!"
United States
Jill W.
$238 nightly
The price is $252
Nov 12 - Nov 13
Total with taxes and fees
In the Country a Beautiful 2-bedroom house with its own private lake

Secluded Lodge with Private Lake Minutes from St. Louis

Millstadt
10.0 out of 10, Exceptional, (210)
"Great hospitality had everything you needed"
United States
michael k.
Secluded Lodge with Private Lake Minutes from St. Louis

Beautiful Modern Loft In Wine Country!

Ste. Genevieve
10.0 out of 10, Exceptional, (270)
"Beautiful loft on beautiful property!"
United States
Addison G.
$170 nightly
The price is $181
Nov 24 - Nov 25
Total with taxes and fees
Beautiful Modern Loft In Wine Country!

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

2.0 star property
Ste. Genevieve
10.0 out of 10, Exceptional, (14)
"Awesome from checking in to all of the place was excellent!!"
United States
Michelle A.
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

Doves Nest Guest House<br> Tranquil & Relaxing

Ste. Genevieve
10.0 out of 10, Exceptional, (52)
"Comfortable stay with nice decor and relaxing atmosphere "
United States
Michael L.
$268 nightly
The price is $268
Nov 17 - Nov 18
Total with taxes and fees
Doves Nest Guest House<br> Tranquil & Relaxing

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

Ste. Genevieve
10.0 out of 10, Exceptional, (58)
"My son's wedding was at Pebble Creek Farms and having this cabin was great because my the whole family could stay together in one spot. It was roomy , super clean and very peaceful. "
United States
Janet G.
$361 nightly
The price is $361
Nov 16 - Nov 17
Total with taxes and fees
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

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.
$258 nightly
The price is $258
Nov 12 - Nov 13
Total with taxes and fees
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Ste. Genevieve
10.0 out of 10, Exceptional, (174)
"We loved staying here!! The host is amazing and it feels like home away from home!"
United States
Mia S.
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

Waterloo
10.0 out of 10, Exceptional, (123)
"The cabin was clean and cozy and perfect location to all the breweries and restaurants we wanted to check out. And loved that it was pet friendly since we love bringing our dog with us everywhere! Highly recommend! "
United States
Amy G.
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Ste. Genevieve
10.0 out of 10, Exceptional, (136)
"It’s perfect and already booking next year!"
United States
Joan H.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

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.
$269 nightly
The price is $281
Nov 11 - Nov 12
Total with taxes and fees
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Urban Lofts

3.0 star property
Perryville
9.2 out of 10, Wonderful, (17)
"Great place to stay! "
United States
Eric
Urban Lofts

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
$212 nightly
The price is $225
Nov 13 - Nov 14
Total with taxes and fees
Peter Ray House

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.
$260 nightly
The price is $277
Nov 11 - Nov 12
Total with taxes and fees
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

3.0 star property
Murphysboro
10.0 out of 10, Exceptional, (1)
"This is a very clean and nice apartment within a very close drive to the Kinkaid boat launch. Easy to locate and can fit a car with a boat in tow no problem. This spot was also much more quiet than the campground or RV spots nearby. They have a great porch and a grill and we didn’t bring something for it which made me sad. "
United States
Ross
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Hot Tub & Creek Views: Secluded Perryville Cabin

Perryville
9.8 out of 10, Exceptional, (7)
"Property was excellent house was really nice and in a great location would stay there again for sure "
United States
David R.
Hot Tub & Creek Views: Secluded Perryville Cabin

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.
$226 nightly
The price is $240
Dec 1 - Dec 2
Total with taxes and fees
Homestead Hideaway + 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

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $146 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Fort Kaskaskia and Kaskaskia Bell.

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.