Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”

Ste. Genevieve
The price is AU$275 per night from 10 Apr to 11 Apr
AU$275
includes taxes & fees
10 Apr - 11 Apr
With a stay at this vacation home in Ste Genevieve, you'll be within a 10-minute drive of Mississippi River and Bolduc House Museum.
"Little Brick House on Main (1865)”
Charming small town! Whole house

Charming small town! Whole house

Maeystown
The price is AU$263 per night from 17 Apr to 18 Apr
AU$263
includes taxes & fees
17 Apr - 18 Apr
When you stay at this vacation home in Maeystown, you'll be 14 minutes by car from Illinois Caverns State Natural Area.
Charming small town! Whole house
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing

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

Ste. Genevieve
With a stay at this vacation home in Ste Genevieve, you'll be within a 10-minute drive of Mississippi River and Ste. Genevieve Historic District.
Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing
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Peaceful Country Home

Peaceful Country Home

Marissa
The price is AU$443 per night from 6 Apr to 7 Apr
AU$443
includes taxes & fees
6 Apr - 7 Apr
This family-friendly vacation home is 7.7 mi (12.5 km) from World Shooting and Recreational Complex and 11.5 mi (18.4 km) from Fayetteville Community Park.
Peaceful Country Home
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!
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
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
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

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

Ste. Genevieve
With a stay at this vacation home, you'll be centrally located in Ste Genevieve, within a 10-minute drive of Mississippi River and Ste Genevieve Museum Learning ...
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
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!
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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
48 Holiday Homes
Lowest Price
AU$125
Highest Price
AU$443
Popular accommodation
"Little Brick House on Main (1865)”, Charming small town! Whole house , Wren’s Hideaway Sleeps 8 Historic downtown neighborhood Charming & Relaxing, Peaceful Country Home, Missouri Castle w/ Private Lake, Pool & 100 Acres!, Secluded Lodge with Private Lake Minutes from St. Louis, Country Home for the Family, Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist, Ste Genevieve Home on 17 Acres, Near Wineries!

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$148 per night from 6 Apr to 7 Apr
AU$148
includes taxes & fees
6 Apr - 7 Apr
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$182 per night from 28 Apr to 29 Apr
AU$182
includes taxes & fees
28 Apr - 29 Apr
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
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$125 per night from 4 May to 5 May
AU$125
includes taxes & fees
4 May - 5 May
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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Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 out of 5
2020 Jefferson St, Perryville, MO
Fully refundable
The price is AU$186 per night from 13 Apr to 14 Apr
AU$186
includes taxes & fees
13 Apr - 14 Apr
When you stay at Holiday Inn Express & Suites Perryville by IHG in Perryville, you'll be within a 5-minute drive of National Shrine of Our Lady of the Miraculous ...
Holiday Inn Express & Suites Perryville by IHG
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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.