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Featured Holiday Homes in Chester

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

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

Ste. Genevieve
A stay at this vacation home places you in the heart of Ste Genevieve, steps from Ste Genevieve Museum Learning Center and 3 minutes by foot from Ste. Genevieve ...
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Sweet Farm Stay

Sweet Farm Stay

Freeburg
The price is AU$277 per night from 1 Jan to 2 Jan
AU$277
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at this vacation home in Freeburg, you'll be on a river, and 30.2 mi (48.5 km) from St. Louis Union Station and 29 mi (46.7 km) from Dome at America’s ...
Sweet Farm Stay
Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4

Ste.Genevieve
With a stay at this vacation home, you'll be centrally located in Ste Genevieve, just a 4-minute walk from Bolduc House Museum and 7 minutes by foot from Felix ...
Cozy Haven Little Hidden Gem Sleeps 4
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Secluded Lodge with Private Lake Minutes from St. Louis

Secluded Lodge with Private Lake Minutes from St. Louis

Millstadt
With a stay at this vacation home in Millstadt, you'll be on a lake, and 6.4 mi (10.3 km) from The Edge and 6.8 mi (11 km) from Memorial Hospital.
Secluded Lodge with Private Lake Minutes from St. Louis
Missouri Castle w/ Private Lake, Pool & 100 Acres!

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

Saint Mary
Located in St Mary, this vacation home is on the waterfront, within a 15-minute drive of Mark Twain National Forest and Cave Vineyard.
Missouri Castle w/ Private Lake, Pool & 100 Acres!
Countryside Private Guest Room

Countryside Private Guest Room

Freeburg
The price is AU$155 per night from 28 Dec to 29 Dec
AU$155
includes taxes & fees
28 Dec - 29 Dec
Located in Freeburg, this vacation home is a 2-minute drive from American Legion Freedom Park and 10 minutes from Hazel Creek.
Countryside Private Guest Room
Tiny Houses of French Village

Tiny Houses of French Village

2.5 out of 5
5953 Brickey Rd, French Village, MO
The price is AU$488 per night from 24 Dec to 25 Dec
AU$488
includes taxes & fees
24 Dec - 25 Dec
With a stay at Tiny Houses of French Village in French Village, you'll be 11.4 mi (18.3 km) from Big River and 12.4 mi (19.9 km) from Goff Spring Lake.
Tiny Houses of French Village
Ste Genevieve Home on 17 Acres, Near Wineries!

Ste Genevieve Home on 17 Acres, Near Wineries!

New Offenburg
Located in St Mary, this vacation home is a 1-minute drive from Mark Twain National Forest and 9 minutes from Crown Valley Winery.
Ste Genevieve Home on 17 Acres, Near Wineries!
Country Home for the Family

Country Home for the Family

Vergennes
With a stay at this vacation home in Vergennes, you'll be 14.3 mi (23.1 km) from Shawnee National Forest and 9.2 mi (14.8 km) from Beaver Lake.
Country Home for the Family
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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.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
43 Holiday Homes
Lowest Price
AU$118
Highest Price
AU$488
Popular accommodation
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist, Sweet Farm Stay, Cozy Haven Little Hidden Gem Sleeps 4, Secluded Lodge with Private Lake Minutes from St. Louis, Missouri Castle w/ Private Lake, Pool & 100 Acres!, Countryside Private Guest Room, Tiny Houses of French Village, Ste Genevieve Home on 17 Acres, Near Wineries!, Country Home for the Family

Top trending hotels in Chester

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is AU$135 per night from 25 Dec to 26 Dec
AU$135
includes taxes & fees
25 Dec - 26 Dec
Located in Chester, Baymont by Wyndham Chester IL is within a 5-minute drive of Chester Skating Rink and Popeye Museum.
Baymont by Wyndham Chester IL
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

2.5 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 25 Dec to 26 Dec
AU$154
includes taxes & fees
25 Dec - 26 Dec
Located in Festus, La Quinta Inn & Suites by Wyndham Festus - St. Louis South is in a rural location, within a 5-minute drive of Jorkerst Memorial Park and Festus ...
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Holiday Inn Express & Suites Perryville, an IHG Hotel

Holiday Inn Express & Suites Perryville, an IHG Hotel

2.5 out of 5
2020 Jefferson St, Perryville, MO
Fully refundable
The price is AU$167 per night from 23 Jan to 24 Jan
AU$167
includes taxes & fees
23 Jan - 24 Jan 2025
When you stay at Holiday Inn Express & Suites Perryville, an IHG Hotel in Perryville, you'll be within a 5-minute drive of National Shrine of Our Lady of the ...
Holiday Inn Express & Suites Perryville, an IHG Hotel
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Super 8 by Wyndham Perryville

Super 8 by Wyndham Perryville

2 out of 5
1119 Vincent Dr, Perryville, MO
Fully refundableReserve now, pay when you stay
The price is AU$118 per night from 12 Jan to 13 Jan
AU$118
includes taxes & fees
12 Jan - 13 Jan 2025
With a stay at Super 8 by Wyndham Perryville in Perryville, you'll be within a 5-minute drive of Perryville Country Club and National Shrine of Our Lady of the ...
Super 8 by Wyndham Perryville
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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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^Subject to availability and chosen travel dates.