Chester Vacation Rentals

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Vacation Rentals in Chester

Postcard Cabins St. Francois

2.0 star property
10.0 out of 10, Exceptional, (23)
"Had a wonderful time"
The price is CA $123
CA $184 total
includes taxes & fees
Aug 6 - Aug 7
Postcard Cabins St. Francois

Missouri Castle w/ Private Lake, Pool & 100 Acres!

10.0 out of 10, Exceptional, (5)
"My family of 14 people needed a place for all of us to stay for the holidays. The twin turrets was a great fit for what we needed. Everyone had their own bed, the bathrooms took a little time to get showers scheduled, since there are only 2 showers, but it worked out. The home was fun to explore inside and out. We went for some walks on the trails, enjoyed watching the ducks and geese, or just looking out at the lake. So peaceful! "
Missouri Castle w/ Private Lake, Pool & 100 Acres!

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (80)
"It was a perfect place for our family to gather for my grandsons 1st birthday"
Private Cabin with Pond on Family Farm

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (259)
"Perfect location for a quiet getaway "
The price is CA $204
CA $246 total
includes taxes & fees
Sep 5 - Sep 6
Beautiful Modern Loft In Wine Country!

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (206)
"My wife really liked the rustic feel of the place and was impressed with how clean it was at the same time. For me, it felt like a retirement property that I’d had for years, it was very welcoming. We didn’t take advantage of the water (kayaks, fishing, etc..) but we had friends over and used the grill to cook. We’d take our dogs outside in the back of the house and there was never any problem. The point of this stay was to visit friends, watch old movies, relax, and do some studying, it was a...
Secluded Lodge with Private Lake Minutes from St. Louis

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

10.0 out of 10, Exceptional, (131)
"Emma was a great host and our group had a ton of fun!"
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Doves Nest Guest House<br> Tranquil & Relaxing

10.0 out of 10, Exceptional, (41)
"Communication with the owners was top notch. Loved being able to walk to town and explore the historic places. "
The price is CA $176
CA $315 total
includes taxes & fees
Aug 6 - Aug 7
Doves Nest Guest House<br> Tranquil & Relaxing

⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4

2.0 star property
9.8 out of 10, Exceptional, (7)
"Amazing property super quiet and chill."
The price is CA $167
CA $294 total
includes taxes & fees
Aug 13 - Aug 14
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4

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

10.0 out of 10, Exceptional, (75)
"Fully stocked. Had everything we could ever want. Very clean and comfortable."
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

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

10.0 out of 10, Exceptional, (55)
"Wonderful place to stay in Ste Genevieve wine country"
The price is CA $372
CA $500 total
includes taxes & fees
Aug 17 - Aug 18
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Sweet Farm Stay

9.8 out of 10, Exceptional, (38)
"We had a very pleasant stay"
The price is CA $186
CA $226 total
includes taxes & fees
Aug 6 - Aug 7
Sweet Farm Stay

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

10.0 out of 10, Exceptional, (2)
"Tiny house was absolutely perfect for a quick getaway or even a longer stay had everything we needed except a toaster! Owners were great on getting in touch for anything needed."
The price is CA $272
CA $354 total
includes taxes & fees
Aug 17 - Aug 18
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

33ft private pool+4bd 2b+Arcade+nature+stargazing

33ft private pool+4bd 2b+Arcade+nature+stargazing

Countryside Private Guest Room

10.0 out of 10, Exceptional, (16)
"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 ."
The price is CA $93
CA $128 total
includes taxes & fees
Aug 9 - Aug 10
Countryside Private Guest Room

"Little Brick House on Main (1865)”

10.0 out of 10, Exceptional, (50)
"The property is a lovely little house, close to places to eat and attractions. "
The price is CA $164
CA $219 total
includes taxes & fees
Aug 13 - Aug 14
"Little Brick House on Main (1865)”

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

10.0 out of 10, Exceptional, (1)
"Newly remodeled home. Very nice and clean. Beautiful views and a great place to relax and get away! "
The price is CA $222
CA $431 total
includes taxes & fees
Aug 8 - Aug 9
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

TreeLoft at BaseCamp

2.0 star property
10.0 out of 10, Exceptional, (4)
"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. "
The price is CA $434
CA $678 total
includes taxes & fees
Aug 10 - Aug 11
TreeLoft at BaseCamp

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

10.0 out of 10, Exceptional, (165)
"Nice location, clean and inviting."
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Hot Tub & Creek Views: Secluded Perryville Cabin

10.0 out of 10, Exceptional, (2)
"Property was excellent house was really nice and in a great location would stay there again for sure "
Hot Tub & Creek Views: Secluded Perryville Cabin

Urban Lofts

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

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?

Missouri Castle w/ Private Lake, Pool & 100 Acres!: This vacation home rental outside of Chester is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.