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Compare 52 Vacation Homes in Chester with updated reviews, rates, and availability.

"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
2 Apr - 3 Apr
"Little Brick House on Main (1865)”

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
30 Mar - 31 Mar
Charming small town! Whole house

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

10.0 out of 10, Exceptional, (18)
"We were there for a family funeral. There was virtual nothing wrong with the home. I am persnickety do I did notice a spot on the hallway floor. My sister did not. I didn’t check it or try to clean it. I just went in with the events of the day. We had tornado warnings and there were zero issues. Again, I don’t think we can say enough regarding the graciousness of our hosts. I would highly recommend this home. "
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing

Peaceful Country Home

10.0 out of 10, Exceptional, (43)
"Lovely, location. Will return. Hosts have attention to detail. Very clean and neat. We’ll labeled and great instructions."
The price is AED 514
AED 930 total
includes taxes & fees
30 Mar - 31 Mar
Peaceful Country Home

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!

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (200)
"We spent 2 very relaxing nights here and loved every minute of it. "
Secluded Lodge with Private Lake Minutes from St. Louis

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

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

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!

Elegant 3BR in the Heart of Historic Ste Genevieve

10.0 out of 10, Exceptional, (3)
"Gorgeous interior decorating and home was very clean. Plenty of room for a family - bedrooms are very big and beds are super comfortable! "
Elegant 3BR in the Heart of Historic Ste Genevieve

Farmstead home w/hot tub

9.8 out of 10, Exceptional, (9)
"Stayed at this location with two other coworkers. We have larger work trucks, so the large driveway made it easy to accommodate our vehicles. The house itself is spacious with a nice front area to hang out and watch shows. Host was very kind and responsive when any communication was needed."
The price is AED 606
AED 1,076 total
includes taxes & fees
30 Mar - 31 Mar
Farmstead home w/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

Homestead Hideaway + Hot Tub

10.0 out of 10, Exceptional, (25)
"Clean easy property just like the listing. Rural and secluded. Perfect spot "
The price is AED 441
AED 819 total
includes taxes & fees
31 Mar - 1 Apr
Homestead Hideaway + Hot Tub

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!

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
28 Mar - 29 Mar
Countryside Private Guest Room

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
30 Mar - 31 Mar
Tiny Houses of French Village

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!

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

Doves Nest Guest House<br> Tranquil & Relaxing

9.8 out of 10, Exceptional, (37)
"We come down to Ste Genevieve for sister trip several times a year. Our parents live down there and we just make it a winery /sister weekend when we visit. This is the first time staying at this house though it has been in my radar for a while. Just adorable. The host thinks of every little detail. And it is decorated so cute. King size bed is one of the most comfortable beds I've slept in. The bedroom and the other room was comfy as well, though I do think it to be a full and not a queen. Not a...
Doves Nest Guest House<br> Tranquil & Relaxing
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, (3)
"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 331
AED 356 total
includes taxes & fees
10 Apr - 11 Apr
Postcard Cabins St. Francois

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (68)
"Beautiful property, very friendly owner that is very accommodating. Most relaxing 2 days ive had in years. Very peaceful stay! Will definitely be back!"
Private Cabin with Pond on Family Farm

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

10.0 out of 10, Exceptional, (18)
"We were there for a family funeral. There was virtual nothing wrong with the home. I am persnickety do I did notice a spot on the hallway floor. My sister did not. I didn’t check it or try to clean it. I just went in with the events of the day. We had tornado warnings and there were zero issues. Again, I don’t think we can say enough regarding the graciousness of our hosts. I would highly recommend this home. "
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
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.