Chester Vacation Rentals from ￥13,078: Search Short-Term Rentals

Q: 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.

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Vacation Rentals in Chester

Our top choices for Chester vacation rentals

"Sweet cabin"

￥19,606 total

includes taxes & fees

Aug 26 - Aug 27

"Tom is awesome, made sure we had everything we needed and was always helpful if we need anything. Will be back for sure ! 5 "

"Amazing property super quiet and chill."

￥29,756 total

includes taxes & fees

Sep 2 - Sep 3

"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! "

"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...

"Outstanding! I highly recommend to everyone! So well decorated with every amenity! Great location and easy walk to restaurants and activities and shopping! Great hosts!"

￥32,371 total

includes taxes & fees

Sep 2 - Sep 3

"We enjoyed our stay! Peaceful and relaxing.John and Bambi"

"We had a very pleasant stay"

￥24,138 total

includes taxes & fees

Aug 31 - Sep 1

1 bedroom, iron/ironing board, bed sheets

"My view was totally amazing. Very clean and roomy. Bed was very comfortable. Furnished very nice"

￥26,404 total

includes taxes & fees

Aug 28 - Aug 29

"Emma was a great host and our group had a ton of fun!"

1 bedroom, iron/ironing board, free WiFi, bed sheets

"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! "

"What an unforgettable weekend! From the moment we arrived at Bauman's Deep Woods Escape, it was clear that every single detail had been thoughtfully curated for a perfect stay. This place truly lives up to its name—a serene, secluded retreat where relaxation reigns supreme. The amenities? Spot on and exactly as advertised—if not better. If you're dreaming of a peaceful getaway where you can unplug, unwind, and recharge, look no further. Bauman’s is the ultimate escape. We can’t wait to come...

"Wonderful place to stay in Ste Genevieve wine country"

￥53,046 total

includes taxes & fees

Aug 26 - Aug 27

"Nice location, clean and inviting."

￥40,616 total

includes taxes & fees

Sep 1 - Sep 2

"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. "

"Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. "

￥45,986 total

includes taxes & fees

Aug 26 - Aug 27

"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."

￥32,857 total

includes taxes & fees

Aug 26 - Aug 27

"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. "

￥69,503 total

includes taxes & fees

Aug 26 - Aug 27

"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."

￥37,631 total

includes taxes & fees

Aug 26 - Aug 27

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Top Chester Hotel Reviews

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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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?

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.

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Chester Vacation Rentals

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Vacation Rentals in Chester

Our top choices for Chester vacation rentals

Postcard Cabins St. Francois

Private Cabin with Pond on Family Farm

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

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

Secluded Lodge with Private Lake Minutes from St. Louis

Doves Nest Guest House<br> Tranquil & Relaxing

Hot Tub & Creek Views: Secluded Perryville Cabin

Sweet Farm Stay

Beautiful Modern Loft In Wine Country!

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

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

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

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

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

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

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

Peter Ray House

TreeLoft at BaseCamp

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

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

Top Chester Hotel Reviews

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