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Compare 41 Vacation Homes in Chester with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (164)
"Nice location, clean and inviting."
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Cozy 1.5 story bungalow in downtown Ste. Genevieve!

9.8 out of 10, Exceptional, (11)
"Spent one night, explored St Genevieve. We had everything needed and host was most accommodating. The upstairs bedroom has low clearance but not an issue for us. "
Cozy 1.5 story bungalow in downtown Ste. Genevieve!

Sweet Farm Stay

10.0 out of 10, Exceptional, (27)
"Jill and her husband were so nice. From the snacks they brought to being flexible when we needed to add days. We especially appreciated being able to bring our dogs, and they loved Dexter. The farmhouse was cozy and comfortable. It felt like being at home. I highly recommend the farmhouse."
The price is AED 551
AED 629 total
includes taxes & fees
24 Feb - 25 Feb
Sweet Farm Stay

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (199)
"Great weekend getaway"
Secluded Lodge with Private Lake Minutes from St. Louis

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

10.0 out of 10, Exceptional, (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! "
Missouri Castle w/ Private Lake, Pool & 100 Acres!

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 AED 907
AED 1,344 total
includes taxes & fees
24 Feb - 25 Feb
Tiny Houses of French Village

Charming small town! Whole house

9.8 out of 10, Exceptional, (7)
"Such a cute, quite town. The home is close to everything! Super clean. Plenty of room for the dogs backyard. I will stay there again! backybackyard. I will stay there aga"
The price is AED 331
AED 604 total
includes taxes & fees
2 Mar - 3 Mar
Charming small town! Whole house

Countryside Private Guest Room

10.0 out of 10, Exceptional, (12)
"Nice hosts…great communication "
The price is AED 275
AED 349 total
includes taxes & fees
24 Feb - 25 Feb
Countryside Private Guest Room

Ste Genevieve Home on 17 Acres, Near Wineries!

9.8 out of 10, Exceptional, (7)
"We stayed at this property for my birthday weekend and it was fabulous! We cooked several meals and the kitchen had EVERYTHING! The house is nestled in the woods, with beautiful surroundings and the house is so cozy. I would definitely stay here again!"
Ste Genevieve Home on 17 Acres, Near Wineries!

Homestead Hideaway + Hot Tub

10.0 out of 10, Exceptional, (24)
"Clean easy property just like the listing. Rural and secluded. Perfect spot "
The price is AED 441
AED 823 total
includes taxes & fees
2 Mar - 3 Mar
Homestead Hideaway + Hot Tub

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

10.0 out of 10, Exceptional, (123)
"Property was amazing as were the hosts. We stayed for a week and had family and friends over the course of the week. It was a perfect venue with a large kitchen to gather with anything you could possibly need (including a drawer full of spices in case you forgot something ;), a game room for hanging/playing games, and the living room has a large TV and surround sound with a huge sofa so we enjoyed watching a movie or two. There is a Sonos sound system that covers every area of the property which...
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, (69)
"We stayed with a group of friends over the superbowl weekend. We have stayed here before and we loved it just as much the second time as we did the first. The owner makes things easy for those who stay from her communication with you to the checkout process. The amenities are amazing. We had a great time and we will stay again!"
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

"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 AED 485
AED 632 total
includes taxes & fees
24 Feb - 25 Feb
"Little Brick House on Main (1865)”

Ste. Genevieve Co. House w/ HOT TUB!

9.8 out of 10, Exceptional, (6)
"very clean and large enough to use for our group"
Ste. Genevieve Co. House w/ HOT TUB!

Country Home for the Family

10.0 out of 10, Exceptional, (31)
"We loved having room indoors to gather and outdoors to play."
Country Home for the Family

Cozy Haven Little Hidden Gem Sleeps 4

10.0 out of 10, Exceptional, (38)
"It was relaxing and peaceful."
Cozy Haven Little Hidden Gem Sleeps 4

Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing

10.0 out of 10, Exceptional, (16)
"We absolutely love Wren's Hideaway. It's spacious and super clean. The coffee bar is awesome, and we had fun showing our kids how WE used to listen to music...on a record player. The beds are very comfortable, as is the house in general. Communication with the owners was great. They recommended several restaurants at my request. However, we only made it to one (Sirros) due to the fact that we ate there two days in a row because it was so good. We highly recommend Wren's Hideaway, and we hope to...
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing

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

Farm-Style Ste. Genevieve Retreat w/ Fire Pit!

9.8 out of 10, Exceptional, (49)
"This is a wonderful place to get away from it all and just enjoy nature and the company of the people you are traveling with. Bird watchers will especially love the barn willows, red headed woodpeckers, blue grosbeak, Bobwhite, and more. Stores and the historic downtown of Saint Genevieve are just a short drive away. Along with many wineries."
Farm-Style Ste. Genevieve Retreat w/ Fire Pit!

Stonehaven Ranch LLC, Memories set in stone

10.0 out of 10, Exceptional, (13)
"Beautifully decorated quaint cottage. has everything you need to relax. "
The price is AED 459
AED 659 total
includes taxes & fees
25 Feb - 26 Feb
Stonehaven Ranch LLC, Memories set in stone
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 property types in Chester

Postcard Cabins St. Francois

2.0 star property
10.0 out of 10, Exceptional, (2)
"This place made me look like a rockstar to my wife. I surprised her with a V day getaway. The cabin was awesome. We loved the view of nature from the large window. I made dinner reservations nearby at the weingarten vineyard. The hiking trail along the creek was fun. We ate breakfast right down the road at Kozy. For our final night I cooked steaks over the open fire"
The price is AED 294
AED 316 total
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins St. Francois

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

"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 AED 485
AED 632 total
includes taxes & fees
24 Feb - 25 Feb
"Little Brick House on Main (1865)”
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.