Book Holiday Homes in Chester
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Featured Holiday Homes in Chester
Dog-friendly chalet cabin with valley view, deck, and private hot tub
New Ludlow Village Home with Stunning Okemo Mountain View
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Primely Located Dover Escape < 1 Mi to Mt Snow!
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
Cozy Cabin Between Stratton Resort & Mount Snow
Charming 3-bedroom house in Ludlow with WiFi access
The Green Mountain Chapel // Old Church repositioned into 3 BR
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 | 879 Holiday Homes |
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Lowest Price | NZ$263 |
Highest Price | NZ$2,126 |
Popular accommodation | Dog-friendly chalet cabin with valley view, deck, and private hot tub, New Ludlow Village Home with Stunning Okemo Mountain View, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, BruinsDen - Ski On Ski Off (Home Stretch Trail), Primely Located Dover Escape < 1 Mi to Mt Snow!, Fabulous Mountain Top Retreat - 10 minutes from mount snow!, Cozy Cabin Between Stratton Resort & Mount Snow, Charming 3-bedroom house in Ludlow with WiFi access, The Green Mountain Chapel // Old Church repositioned into 3 BR |
More accommodations in Chester
Top trending hotels in Chester
Stone Hearth Inn and Eatery
Woodstock Inn & Resort
Hampton Inn and Suites Manchester
Pointe at Castle Hill Resort
More ways to explore Chester
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^Subject to availability and chosen travel dates.