Book Holiday Homes in Chester
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Featured Holiday Homes in Chester

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Cozy Home Near Downtown, Shops, and Restaurants.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Potter's Place | House in Jamaica with mountain views

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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 | 1086 Holiday Homes |
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Lowest Price | AU$222 |
Highest Price | AU$947 |
Popular accommodation | Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Cozy Home Near Downtown, Shops, and Restaurants., Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Potter's Place | House in Jamaica with mountain views, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. |
Top Locations for Holiday Homes in Chester
Top trending hotels in Chester

Fullerton Inn

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Woodstock Inn & Resort

The Equinox Golf Resort & Spa
More ways to explore Chester
Top picks
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^Subject to availability and chosen travel dates.