Chester Holiday Homes
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Chester
Beautiful Private Stone Home in the Hudson Valley
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Nature Getaway: Charming Villa Near Trails and Parks
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
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 | 286 Holiday Homes |
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Lowest Price | AU$173 |
Highest Price | AU$2,000 |
Popular accommodation | Beautiful Private Stone Home in the Hudson Valley, Red Barn Retreat - Shawangunk Mountains Getaway, complete privacy vacation home [private pool], Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!, Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!, 'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, Nature Getaway: Charming Villa Near Trails and Parks, Pet-Friendly ‘Pond View Loft' w/ Private Pool!, Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake |
Holiday Homes in Chester
Top Locations for Holiday Homes in Chester
More accommodations in Chester
Top trending hotels in Chester
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
DoubleTree by Hilton Hotel Nanuet
Best Western Fishkill Inn & Suites
Overlook Lodge at Bear Mountain
More ways to explore Chester
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.