Holiday Rentals in Chester

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Holiday Rentals in Chester

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (59)
"We loved the cabin! Owners were so kind and accommodating! Beds & pillows were feathery and so comfy! We loved having 2 complete levels to spread out in. We had a great time and will definitely book again!! Our only ding in an otherwise perfect review is that the oven didn’t work very well & we couldn’t see the oven temp hardly at all. It was a little frustrating trying to cook for a family. Also, only service for 4 for a cabin that sleeps 6. Good thing we brought our own paper plates. But...
Private Cabin with Pond on Family Farm

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

10.0 out of 10, Exceptional, (164)
"We come here annually and love the memories made in this home to kick off the holidays! "
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Sweet Farm Stay

10.0 out of 10, Exceptional, (26)
"Very nice location out in the middle of nowhere! Our dogs loved the huge yard and liked talking with Dexter! Clean and very comfortable! Will definitely consider staying again if we come back to the area!"
The price is €171
includes taxes & fees
19 Jan - 20 Jan
Sweet Farm Stay

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (196)
"My best friend of 50 years and I spent four days at this lovely house. The hosts were wonderful; answered any questions we had very promptly. We are both in our 70s and the stairs were more of a challenge than I had anticipated from the pictures, but we managed. The house is lovely, the grounds are great and the fishing was awesome. We would definitely recommend this or a quiet getaway, especially if you like to fish."
Secluded Lodge with Private Lake Minutes from St. Louis

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (243)
"My wife and I really enjoyed the quiet and character of this lovely loft. Very smart property. We can't wait to come back this summer because the beautiful lake looked really inviting. We visited two great wineries, two of many, that were local to this loft. Class class class, Julie and Keith. Thank you both."
The price is €179
includes taxes & fees
14 Jan - 15 Jan
Beautiful Modern Loft In Wine Country!

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

10.0 out of 10, Exceptional, (3)
"Our group stayed here after a larger family reunion at Trout Lodge, YMCA. The place was great with something to do for everyone. Having a private, CLEAN pool for the family is amazing. We hiked around and boated around the lake, made s’mores by a campfire, played pool and darts and board games and grilled meals. This house lets you do it all and has the space to visit family and also have alone time. I’d love to come back."
Missouri Castle w/ Private Lake, Pool & 100 Acres!

Country Home for the Family

10.0 out of 10, Exceptional, (30)
"We loved having room indoors to gather and outdoors to play."
Country Home for the Family

Charming small town! Whole house

9.8 out of 10, Exceptional, (6)
"Such a charming place. We were traveling back home to central Wisconsin from Houston Texas and this was the perfect place to relax. Would love to check it out for a weekend and get to know more about the home itself and the immediate area. Thank you so much for the accommodations. "
The price is €164
includes taxes & fees
11 Feb - 12 Feb
Charming small town! Whole house

Countryside Private Guest Room

10.0 out of 10, Exceptional, (12)
"Nice hosts…great communication "
The price is €97
includes taxes & fees
19 Jan - 20 Jan
Countryside Private Guest Room

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

10.0 out of 10, Exceptional, (113)
"We came to Waterloo to visit family for Christmas. We always wanted to stay in a log cabin. This one didn’t disappoint. We loved everything about it! The bed was so comfortable, we slept in every single day! The owners were very easy to get ahold of. Great experience all around!"
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

Downtown historic main street

9.6 out of 10, Exceptional, (179)
"Great location down town, able to walk to shops and restaurants. "
Downtown historic main street

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

10.0 out of 10, Exceptional, (121)
"We came in town for a short weekend, as a group of 14. Plenty of room for all of us and lots of activities for all ages. The kitchen is very well stocked with everything you could need. We are already talking about returning to this property, or the neighboring one. Thanks, Emma for your hospitality! "
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Tiny Houses of French Village

2.5 star property
10.0 out of 10, Exceptional, (2)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
The price is €357
includes taxes & fees
12 Jan - 13 Jan
Tiny Houses of French Village

Peter Ray House

10.0 out of 10, Exceptional, (60)
"Plenty of room to spread out if you needed yet enough room for family game or movie night.Perfect for one or six"
Peter Ray House

The 1801 House: A beautiful historic home in the Ste Genevieve Historic District

10.0 out of 10, Exceptional, (111)
"This is a very charming and cozy house. It was very clean and the appliances were all new/newer. The home has 1 queen bed, 1 full bed, and 1 king. They also have a blow up bed in the closet. Great selection of k cup coffees and tea bags. A very special surprise of gooey butter cakes from Pats, the local pastry shop."
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District

Bridal Suite, Firepit, Shuffleboard, Foosball, & Rooftop deck: 30 min from STL

2.0 star property
10.0 out of 10, Exceptional, (4)
"We were so happy with this VRBO! The welcome gift of artisan cookies - fully stocked kitchen - comfortable beds - upgrade linens and towels. We loved our stay! We did have our 84 year old mother and there are a lot of steps so if someone cannot do stairs well it is not the place for you. But otherwise it was an amazing place to stay! "
Bridal Suite, Firepit, Shuffleboard, Foosball, & Rooftop deck: 30 min from STL

"Little Brick House on Main (1865)”

10.0 out of 10, Exceptional, (39)
"We were there for our grandson's wedding. This little house exceeded all expectation. Just lovely and with so many extra thoughtful touches, i.e. pumpkins and fall flowers for cozy October. Too many to list. "
The price is €171
includes taxes & fees
12 Jan - 13 Jan
"Little Brick House on Main (1865)”

Homestead Hideaway + Hot Tub

10.0 out of 10, Exceptional, (23)
"This was our second stay at the Homestead Hideaway and we had another great time! The location of the property is perfect - we watched deer walk by in the mornings and enjoyed the quiet evenings. Hailey is so easy to work with and has a ton of amenities provided for her guests. We will stay again!"
The price is €224
includes taxes & fees
13 Jan - 14 Jan
Homestead Hideaway + Hot Tub

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

10.0 out of 10, Exceptional, (68)
"Fully stocked. Had everything we could ever want. Very clean and comfortable."
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

10.0 out of 10, Exceptional, (17)
"They had snacks waiting for us 👍"
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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Other types of properties in Chester you may be interested in

Baymont by Wyndham Chester IL

2.5 star property
8.6 out of 10, Excellent, (280)
"The stay was comfortable!"
The price is €87
includes taxes & fees
12 Jan - 13 Jan
Baymont by Wyndham Chester IL

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

2.5 star property
8.0 out of 10, Very good, (728)
"very convenient location"
The price is €101
includes taxes & fees
19 Jan - 20 Jan
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

Holiday Inn Express & Suites Perryville, an IHG Hotel

2.5 star property
9.4 out of 10, Exceptional, (431)
"Very friendly staff and good breakfast "
The price is €97
includes taxes & fees
6 Feb - 7 Feb
Holiday Inn Express & Suites Perryville, an IHG Hotel
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.

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Chester Skating Rink, 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?

Secluded Lodge with Private Lake Minutes from St. Louis: 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. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chester Skating Rink. Other places in town to visit include Popeye Museum 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.