Holiday Homes in Chester

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Featured Holiday Homes in Chester

Sweet Farm Stay

10.0 out of 10, Exceptional, (24)
"We only spent one evening there, but it was peaceful and lovely!"
The price is AU$266
includes taxes & fees
29 Nov - 30 Nov
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

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

Countryside Private Guest Room

10.0 out of 10, Exceptional, (11)
"The room was clean & well kept. Everything we needed was already there. Toiletries, towels, bedding, coffee, bottled water & more. Beautiful property & very quiet. The host were very nice folks. We would definitely stay again. "
The price is AU$149
includes taxes & fees
27 Nov - 28 Nov
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 AU$470
includes taxes & fees
1 Dec - 2 Dec
Tiny Houses of French Village

Ste. Genevieve Co. House w/ HOT TUB!

9.6 out of 10, Exceptional, (5)
"The property could use an update but it was good for what we needed"
Ste. Genevieve Co. House w/ HOT TUB!

Cozy Haven Little Hidden Gem Sleeps 4

10.0 out of 10, Exceptional, (36)
"I will absolutely be returning! "
Cozy Haven Little Hidden Gem Sleeps 4

Private Home, quiet neighborhood, So. IL, close to St. Louis

10.0 out of 10, Exceptional, (18)
"We are repeat stayers in this home and appreciate all the comforts of the property each year! The host is the best in always leaving snacks and beverages; and all the things you would need for a long stay!"
The price is AU$512
includes taxes & fees
25 Dec - 26 Dec
Private Home, quiet neighborhood, So. IL, close to St. Louis

Farmstead home w/hot tub

9.8 out of 10, Exceptional, (8)
"Excellent stay! Clean, great location for World Shooting Complex and close to Sparta. Highly Recommend 🌟 "
The price is AU$446
includes taxes & fees
1 Dec - 2 Dec
Farmstead home w/hot tub

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!

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

Peter Ray House

10.0 out of 10, Exceptional, (58)
"Was so happy staying here - satisfied in every way. The house was just as described (even better than I expected), clean, and comfortable. Communication with Joyce was excellent - she was always available, and very descriptive with the overall checkin/checkout process. I would stay here again in a heartbeat. (:"
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

"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 AU$269
includes taxes & fees
1 Dec - 2 Dec
"Little Brick House on Main (1865)”

Homestead Hideaway + Hot Tub

9.8 out of 10, Exceptional, (20)
"My family and I travel every year in August to attend the Grand All American Shooting Event, this has been the best stay by far. Felt like we were right at home"
The price is AU$351
includes taxes & fees
4 Dec - 5 Dec
Homestead Hideaway + Hot Tub

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

10.0 out of 10, Exceptional, (2)
"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!

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 AU$256
includes taxes & fees
1 Dec - 2 Dec
Charming small town! Whole house

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

10.0 out of 10, Exceptional, (67)
"We held our family Christmas here. 13 people, 7 adults and 6 children. We spent 6 days here. People played pool, ping pong, games, swam and we grilled outside. This house has everything you would in your own home! One day I hosted our huge family gathering of 40+people, plenty of room, it was nice outside and inside and once again everything is provided at the house. I would recommend this house to everyone. Beautiful home. I will rent this house again. Julie"
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

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

10.0 out of 10, Exceptional, (160)
"We were visiting St. Gen to see the new Weingarten that was just renovated and reopened. We had a blast! I love the town and how everything is within walking distance. The house was so cute and clean. Perfect for our group! We will definitely be back!"
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Cozy 1.5 story bungalow in downtown Ste. Genevieve!

9.6 out of 10, Exceptional, (10)
"My husband and I enjoyed the wineries then stayed at the house for one night. It was perfect for a little weekend getaway!"
Cozy 1.5 story bungalow in downtown Ste. Genevieve!
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

Downtown historic main street

9.6 out of 10, Exceptional, (176)
"The area was very eclectic and fun. Very unique area. Needs a little work yet but was informed of that from the get go. "
The price is AU$222
includes taxes & fees
27 Nov - 28 Nov
Downtown historic main street

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (56)
"We are here visiting family and needed a peaceful place to stay. This was exactly what we needed. When we come back to the area, we WILL stay here. Thank you for a great vacation "
Private Cabin with Pond on Family Farm

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
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.