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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

"Little Brick House on Main (1865)”
Interior

"Little Brick House on Main (1865)”

10.0 out of 10, Exceptional, (42)
"We absolutely LOVED staying in this adorable cottage!! We will definitely be going back in the future!"
The price is SAR 495
SAR 645 total
includes taxes & fees
8 May - 9 May
"Little Brick House on Main (1865)”
Charming small town! Whole house
Fridge, microwave, oven, stovetop

Charming small town! Whole house

9.6 out of 10, Exceptional, (8)
"Comfy, clean, good communication with host, thoughtful amenities"
The price is SAR 338
SAR 617 total
includes taxes & fees
5 May - 6 May
Charming small town! Whole house
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
Exterior

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

10.0 out of 10, Exceptional, (20)
"Would stay here again!"
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
Peaceful Country Home
Property grounds

Peaceful Country Home

10.0 out of 10, Exceptional, (44)
"Great stay and place. Location is nice and new paved roads out front. Location is in a weird spot to get to from the main road, will need to take super sharpe right, tough as party were on motorcycles."
The price is SAR 596
SAR 1,040 total
includes taxes & fees
11 May - 12 May
Peaceful Country Home
Missouri Castle w/ Private Lake, Pool & 100 Acres!
Exterior

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

10.0 out of 10, Exceptional, (4)
"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
Pool

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (203)
"Great weekend getaway"
Secluded Lodge with Private Lake Minutes from St. Louis
Country Home for the Family
4 bedrooms, iron/ironing board, bed sheets

Country Home for the Family

10.0 out of 10, Exceptional, (31)
"We enjoyed our weekend getaway. The quiet country house was what we needed. "
Country Home for the Family
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Property grounds

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!
Exterior

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
Miscellaneous

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
Fridge, microwave, oven, stovetop

Farmstead home w/hot tub

9.8 out of 10, Exceptional, (9)
"Excellent stay! Clean, great location for World Shooting Complex and close to Sparta. Highly Recommend 🌟 "
The price is SAR 619
SAR 1,094 total
includes taxes & fees
5 May - 6 May
Farmstead home w/hot tub
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (124)
"The place was amazing, great location, well stocked and supplied and family friendlyI would rate this out of 5 stars a 10cannot say enough about this place"
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Exterior

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

10.0 out of 10, Exceptional, (69)
"Fully stocked. Had everything we could ever want. Very clean and comfortable."
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Homestead Hideaway + Hot Tub
Outdoor spa tub

Homestead Hideaway + Hot Tub

10.0 out of 10, Exceptional, (26)
"Very enjoyable stay!"
The price is SAR 450
SAR 848 total
includes taxes & fees
14 May - 15 May
Homestead Hideaway + Hot Tub
Ste. Genevieve Co. House w/ HOT TUB!
Dining

Ste. Genevieve Co. House w/ HOT TUB!

9.8 out of 10, Exceptional, (6)
"Large space which was great. Big bedrooms. "
Ste. Genevieve Co. House w/ HOT TUB!
Countryside Private Guest Room
Exterior

Countryside Private Guest Room

10.0 out of 10, Exceptional, (12)
"Owners were awesome and it was my first time staying in a B&B . I will never stay in another hotel when visiting StLouis . I was very impressed with the hospitality and location ."
The price is SAR 281
SAR 356 total
includes taxes & fees
5 May - 6 May
Countryside Private Guest Room
Tiny Houses of French Village
House | Living area

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 SAR 926
SAR 1,372 total
includes taxes & fees
5 May - 6 May
Tiny Houses of French Village
Farm-Style Ste. Genevieve Retreat w/ Fire Pit!
Fridge, microwave, stovetop, dishwasher

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

9.8 out of 10, Exceptional, (50)
"House was really clean and bed was comfortable. Great location and close to our wedding venue. Loved our short stay."
Farm-Style Ste. Genevieve Retreat w/ Fire Pit!
Cozy Haven Little Hidden Gem Sleeps 4
1 bedroom, desk, iron/ironing board, travel crib

Cozy Haven Little Hidden Gem Sleeps 4

10.0 out of 10, Exceptional, (40)
"Great host and a cozy place to stay "
Cozy Haven Little Hidden Gem Sleeps 4
Doves Nest Guest House<br> Tranquil & Relaxing
Property grounds

Doves Nest Guest House<br> Tranquil & Relaxing

9.8 out of 10, Exceptional, (38)
"Comfortable stay with nice decor and relaxing atmosphere "
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
Terrace/patio

Postcard Cabins St. Francois

2.0 star property
10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay here. It was a little confusing to find our cabin at first. The cabin was very clean and not outdated in style. It was very quiet and nice for relaxing! I wish there was a tv in the cabin for more entertainment!"
The price is SAR 338
SAR 504 total
includes taxes & fees
18 May - 19 May
Postcard Cabins St. Francois
Private Cabin with Pond on Family Farm
Exterior

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (72)
"Very nice, clean and cozy cabin. We had a great time!"
Private Cabin with Pond on Family Farm
"Little Brick House on Main (1865)”
Interior

"Little Brick House on Main (1865)”

10.0 out of 10, Exceptional, (42)
"We absolutely LOVED staying in this adorable cottage!! We will definitely be going back in the future!"
The price is SAR 495
SAR 645 total
includes taxes & fees
8 May - 9 May
"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.