Search Holiday Rentals in Chester

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday 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 £100
includes taxes & fees
11 Aug - 12 Aug
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)
"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

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (260)
"Perfect location for a quiet getaway "
The price is £139
includes taxes & fees
11 Aug - 12 Aug
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, (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

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 £179
includes taxes & fees
10 Aug - 11 Aug
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 £166
includes taxes & fees
13 Aug - 14 Aug
⚜️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 £278
includes taxes & fees
17 Aug - 18 Aug
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 £126
includes taxes & fees
11 Aug - 12 Aug
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 £196
includes taxes & fees
21 Aug - 22 Aug
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 £72
includes taxes & fees
16 Aug - 17 Aug
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 £132
includes taxes & fees
31 Aug - 1 Sept
"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 £240
includes taxes & fees
8 Aug - 9 Aug
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 £452
includes taxes & fees
15 Aug - 16 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in

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.