Book Holiday Homes in Chester
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Featured Holiday Homes in Chester

"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!
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! |
Holiday Homes in Chester
Top Locations for Holiday Homes in Chester
Top trending hotels in Chester

Baymont by Wyndham Chester IL

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

Super 8 by Wyndham Perryville

Holiday Inn Express & Suites Perryville by IHG
More ways to explore Chester
Top picks
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^Subject to availability and chosen travel dates.