Holiday Rentals in Chester

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Holiday Rentals in Chester

Our top choices for Chester holiday rentals

Postcard Cabins St. Francois

2.0 star property
10.0 out of 10, Exceptional, (27)
"Sweet cabin"
The price is €115
includes taxes & fees
25 Aug - 26 Aug
Postcard Cabins St. Francois

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (83)
"Tom is awesome, made sure we had everything we needed and was always helpful if we need anything. Will be back for sure ! 5 "
Private Cabin with Pond on Family Farm

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

2.0 star property
9.8 out of 10, Exceptional, (8)
"Amazing property super quiet and chill."
The price is €178
includes taxes & fees
2 Sept - 3 Sept
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4

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!

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (207)
"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

Doves Nest Guest House<br> Tranquil & Relaxing

10.0 out of 10, Exceptional, (43)
"Communication with the owners was top notch. Loved being able to walk to town and explore the historic places. "
The price is €193
includes taxes & fees
2 Sept - 3 Sept
Doves Nest Guest House<br> Tranquil & Relaxing

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (261)
"Perfect location for a quiet getaway "
The price is €158
includes taxes & fees
25 Aug - 26 Aug
Beautiful Modern Loft In Wine Country!

Sweet Farm Stay

9.8 out of 10, Exceptional, (39)
"We had a very pleasant stay"
The price is €145
includes taxes & fees
24 Aug - 25 Aug
Sweet Farm Stay

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

10.0 out of 10, Exceptional, (132)
"Emma was a great host and our group had a ton of fun!"
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

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

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

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 €318
includes taxes & fees
24 Aug - 25 Aug
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

3.0 star property
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. "
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

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

10.0 out of 10, Exceptional, (120)
"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! "
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

Peter Ray House

10.0 out of 10, Exceptional, (67)
"House is across alley from my granddaughter’s, making it very convenient for our visit. Enjoyed staying in this beautifully restored and decorated house. This is our second stay and plan on staying here again next year."
The price is €197
includes taxes & fees
27 Aug - 28 Aug
Peter Ray House

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

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

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

10.0 out of 10, Exceptional, (167)
"Nice location, clean and inviting."
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

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

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 €470
includes taxes & fees
24 Aug - 25 Aug
TreeLoft at BaseCamp

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

10.0 out of 10, Exceptional, (27)
"Love the stay and the place!!"
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
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 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?

Missouri Castle w/ Private Lake, Pool & 100 Acres!: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.