
Holiday Homes in Chester
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Our top choices for Chester holiday homes

1. Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. Genevieve
Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. GenevieveSaint Mary
9.8 out of 10, Exceptional, (12 reviews)
The price is AU$575
includes taxes & fees
4 Nov - 5 Nov

2. Tiny Houses of French Village
Tiny Houses of French VillageFrench Village
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$484
includes taxes & fees
4 Nov - 5 Nov

3. 5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp CanaSte. Genevieve
10.0 out of 10, Exceptional, (4 reviews)
The price is AU$375
includes taxes & fees
8 Nov - 9 Nov

4. 5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp CanaNew Offenburg
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$379
includes taxes & fees
4 Nov - 5 Nov

5. Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.Bloomsdale
10.0 out of 10, Exceptional, (20 reviews)
The price is AU$383
includes taxes & fees
8 Nov - 9 Nov

6. Silo Farm Haus- located in the heart of wine country!
Silo Farm Haus- located in the heart of wine country!Ste. Genevieve
10.0 out of 10, Exceptional, (160 reviews)
The price is AU$515
includes taxes & fees
4 Nov - 5 Nov

7. The Weber Farm - Enjoy a beautiful 100 acre farm!
The Weber Farm - Enjoy a beautiful 100 acre farm!Frohna
10.0 out of 10, Exceptional, (34 reviews)
The price is AU$276
includes taxes & fees
1 Dec - 2 Dec

8. Built in 1929 and fully restored in 2022 Where the old and new world meets
Built in 1929 and fully restored in 2022 Where the old and new world meetsMarissa
9.8 out of 10, Exceptional, (6 reviews)
The price is AU$859
includes taxes & fees
15 Nov - 16 Nov

9. Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.Oraville
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$247
includes taxes & fees
4 Nov - 5 Nov

10. Peaceful Country Home
Peaceful Country HomeMarissa
10.0 out of 10, Exceptional, (51 reviews)
The price is AU$411
includes taxes & fees
9 Nov - 10 Nov

11. Countryside Private Guest Room
Countryside Private Guest RoomFreeburg
9.8 out of 10, Exceptional, (32 reviews)
The price is AU$128
includes taxes & fees
9 Nov - 10 Nov

12. Fit and Fueled Studio
Fit and Fueled StudioPinckneyville
9.0 out of 10, Wonderful, (7 reviews)
The price is AU$279
includes taxes & fees
4 Nov - 5 Nov

13. Peter Ray House
Peter Ray HouseMaeystown
10.0 out of 10, Exceptional, (77 reviews)
The price is AU$304
includes taxes & fees
10 Nov - 11 Nov

14. In the Country a Beautiful 2-bedroom house with its own private lake
In the Country a Beautiful 2-bedroom house with its own private lakeWaterloo
10.0 out of 10, Exceptional, (42 reviews)
The price is AU$337
includes taxes & fees
15 Nov - 16 Nov

15. Homestead Hideaway + Hot Tub
Homestead Hideaway + Hot TubFults
10.0 out of 10, Exceptional, (33 reviews)
The price is AU$379
includes taxes & fees
5 Nov - 6 Nov

16. Sweet Farm Stay
Sweet Farm StayFreeburg
9.8 out of 10, Exceptional, (53 reviews)
The price is AU$270
includes taxes & fees
9 Nov - 10 Nov

17. The Yellow Haus, close to downtown Waterloo!
The Yellow Haus, close to downtown Waterloo!Waterloo
9.6 out of 10, Exceptional, (5 reviews)
The price is AU$492
includes taxes & fees
4 Nov - 5 Nov
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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Top Chester Hotel Reviews

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
10/10 Excellent
Find out more about Chester
Chester Holiday Homes information
Number of reviews | 508 |
|---|---|
Accommodation | 58 Holiday Homes |
Lowest Price | AU$128 |
Highest Price | AU$859 |























































