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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. Genevieve
Saint Mary
9.8 out of 10, Exceptional, (12 reviews)
"The house was very clean. It's located in a quiet and safe neighborhood. It was well stocked with cooking utensils. It was pet friendly with a secure fenced backyard. The host was responsive and accommodating. We stayed here while we were in town for work and would stay here again."
United States
Deborah H.
The price is AU$575
includes taxes & fees
4 Nov - 5 Nov
Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. Genevieve

2. Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (6 reviews)
"Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing "
United States
Chris
The price is AU$484
includes taxes & fees
4 Nov - 5 Nov
Tiny Houses of French Village

3. 5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Ste. Genevieve
10.0 out of 10, Exceptional, (4 reviews)
"Perfect size cabin to get away and enjoy nature sitting on front porch. Very clean with all the amenities you need. Erin was very nice and prompt response to any of my questions."
United States
Matt H.
The price is AU$375
includes taxes & fees
8 Nov - 9 Nov
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

4. 5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana

5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
New Offenburg
10.0 out of 10, Exceptional, (2 reviews)
"This was one of the best places I’ve ever stayed. Owner thought of everything and it was so comfortable. The space was perfect, extra blankets, both types of coffee makers, firewood on site. This is a very new property and everything was immaculate and clean. Was easy to navigate check-in and house was so cute! Would definitely recommend to anyone heading to St Gen or any of surrounding areas."
United States
Carole J.
The price is AU$379
includes taxes & fees
4 Nov - 5 Nov
5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana

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)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
United States
Blake H.
The price is AU$383
includes taxes & fees
8 Nov - 9 Nov
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

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)
"We had an amazing time! Great property and cozy. We had a few dead flies in the bed but otherwise perfect stay!"
United States
Anthony S.
The price is AU$515
includes taxes & fees
4 Nov - 5 Nov
Silo Farm Haus- located in the heart of wine country!

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)
"Wonderful time! "
United States
Alison C.
The price is AU$276
includes taxes & fees
1 Dec - 2 Dec
The Weber Farm - Enjoy a beautiful 100 acre farm!

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 meets
Marissa
9.8 out of 10, Exceptional, (6 reviews)
"The host was absolutely great, very thoughtful and had everything there you would need, even had extra things for my young children to play with and use. It is a beautiful house and very well put together. Would definitely stay there again and recommend to visitors."
United States
David M.
The price is AU$859
includes taxes & fees
15 Nov - 16 Nov
Built in 1929 and fully restored in 2022 Where the old and new world meets

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)
"Very nice place, will definitely be back."
United States
Greg W.
The price is AU$247
includes taxes & fees
4 Nov - 5 Nov
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

10. Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (51 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is AU$411
includes taxes & fees
9 Nov - 10 Nov
Peaceful Country Home

11. Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
9.8 out of 10, Exceptional, (32 reviews)
"Awesome place to stay really nice host would highly recommend!!!!"
United States
Cayson P.
The price is AU$128
includes taxes & fees
9 Nov - 10 Nov
Countryside Private Guest Room

12. Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
9.0 out of 10, Wonderful, (7 reviews)
"Great location and nice house for us to stay."
United States
Terry O.
The price is AU$279
includes taxes & fees
4 Nov - 5 Nov
Fit and Fueled Studio

13. Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (77 reviews)
"This house was incredible. Loved the history and ambience of the town. Peter was one of the nicest homes I’ve stayed in over the years. I would highly recommend it."
United States
Eric
The price is AU$304
includes taxes & fees
10 Nov - 11 Nov
Peter Ray House

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 lake
Waterloo
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful place!"
United States
Tina S.
The price is AU$337
includes taxes & fees
15 Nov - 16 Nov
In the Country a Beautiful 2-bedroom house with its own private lake

15. Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (33 reviews)
"Lovely, quiet and comfortable place to stay. My son really enjoyed all the frogs and fresh air. "
United States
Kat O.
The price is AU$379
includes taxes & fees
5 Nov - 6 Nov
Homestead Hideaway + Hot Tub

16. Sweet Farm Stay

Sweet Farm Stay
Freeburg
9.8 out of 10, Exceptional, (53 reviews)
"Jill’s property was peaceful and quiet. We loved our stay. We absolutely loved, Dexter, the donkey and Willow and Marley, the cats. We had a very nice stay. I would not recommend counting the futon as a sleeping option. The bed in the master room was very comfortable, as well as the bed upstairs. Jill was excellent with communication and everything was well written out for check in and check out."
United States
Kellie
The price is AU$270
includes taxes & fees
9 Nov - 10 Nov
Sweet Farm Stay

17. The Yellow Haus, close to downtown Waterloo!

The Yellow Haus, close to downtown Waterloo!
Waterloo
9.6 out of 10, Exceptional, (5 reviews)
"This was a great place to stay! Our family of 6 with 4 “big” kids had plenty of room and a place like this is better than renting 2 hotel rooms."
United States
diane d.
The price is AU$492
includes taxes & fees
4 Nov - 5 Nov
The Yellow Haus, close to downtown Waterloo!
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

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Chester Holiday Homes information

Number of reviews
508
Accommodation
58 Holiday Homes
Lowest Price
AU$128
Highest Price
AU$859