A steel bridge over a river with a white boat.

Holiday Homes in Chester

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chester holiday homes

A living room with a leather sofa, a coffee table, and a television on a wooden shelf.

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 NZ$712
includes taxes & fees
27 Oct - 28 Oct
Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. Genevieve
A wooden deck with two Adirondack chairs and a hammock.

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 NZ$546
includes taxes & fees
26 Oct - 27 Oct
Tiny Houses of French Village
A small, single-story building with a porch, a covered outdoor seating area, and a stone foundation.

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 NZ$480
includes taxes & fees
2 Nov - 3 Nov
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
A small, single-story building with a porch, red chairs, and a fan.

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.
5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
A two-story cylindrical building with a covered porch and a welcoming sign.

5. 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, (158 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 NZ$632
includes taxes & fees
8 Nov - 9 Nov
Silo Farm Haus- located in the heart of wine country!
A modern house with a covered porch, outdoor seating, and a pathway leading to the entrance.

6. 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, (19 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 NZ$494
includes taxes & fees
22 Nov - 23 Nov
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
A bedroom with a bed, a bench, a wooden door, and a light fixture.

7. Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay. Kitchen not real well stocked and no WiFi but perfect for what we needed. "
United States
Brandon H.
The price is NZ$354
includes taxes & fees
23 Oct - 24 Oct
Fit and Fueled Studio
A spacious living room with hardwood flooring, a sofa, a chair, and a small table with a lamp.

8. 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, (5 reviews)
"Very nice place, will definitely be back."
United States
Greg W.
The price is NZ$319
includes taxes & fees
23 Oct - 24 Oct
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
A narrow stone pathway leading to a brick building with a sloped roof.

9. 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 NZ$385
includes taxes & fees
25 Oct - 26 Oct
Peter Ray House
A wooden deck with a bench and a staircase leading to a house.

10. Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (31 reviews)
"Awesome place to stay really nice host would highly recommend!!!!"
United States
Cayson P.
The price is NZ$171
includes taxes & fees
26 Oct - 27 Oct
Countryside Private Guest Room
A red chair and a table with two glasses of wine and a lit fire pit.

11. Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (49 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is NZ$529
includes taxes & fees
1 Nov - 2 Nov
Peaceful Country Home
A two-story cabin with a balcony, surrounded by autumn foliage and a lake.

12. 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, (39 reviews)
"Wonderful place!"
United States
Tina S.
The price is NZ$434
includes taxes & fees
25 Oct - 26 Oct
In the Country a Beautiful 2-bedroom house with its own private lake
A hot tub with a view of a park and trees in the background.

13. 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 NZ$481
includes taxes & fees
5 Nov - 6 Nov
Homestead Hideaway + Hot Tub
A house with a sloped roof and a satellite dish on the side.

14. 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 NZ$306
includes taxes & fees
26 Oct - 27 Oct
Sweet Farm Stay
A living room with a brown leather sofa, blue chairs, a coffee table, a rug, and a console table with a mirror and picture.

15. The Yellow Haus, close to downtown Waterloo!

The Yellow Haus, close to downtown Waterloo!
Waterloo
10.0 out of 10, Exceptional, (3 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 NZ$631
includes taxes & fees
27 Oct - 28 Oct
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

Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

10/10 Excellent
"LOVE the double bench available for 2 suitcases! Top notch, KUDOS on that little thing that meant so much to us as seniors. Breakfast was good, rooms were clean, restaurant was nice. An overall exceptional experience. This stay moved Holiday Inn Express up a few notches on my list."
Denise 1-night trip
Posted 9 hours ago
Holiday Inn Express & Suites Perryville by IHG

Find out more about Chester

Chester Holiday Homes information

Number of reviews
442
Accommodation
57 Holiday Homes
Lowest Price
NZ$171
Highest Price
NZ$712