Book Holiday Homes in Winchester
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Featured Holiday Homes in Winchester

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!

A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

LAKE HOUSE ON ROCKY FORK!

Peaceful Country Retreat 20 acres Private Pond

'Small Town Getaway'

Tranquility Cottage | 3 Bed, 1.5 Bath

Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Winchester 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 Winchester vacation homes are the perfect way for you to wing it.
Holiday houses in Winchester 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 Winchester 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 Winchester adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchester 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 Winchester 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.
Winchester Holiday Homes essential information
Accommodation | 46 Holiday Homes |
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Lowest Price | AU$89 |
Highest Price | AU$196 |
Popular accommodation | McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events, THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!, A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More, Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond, LAKE HOUSE ON ROCKY FORK!, Peaceful Country Retreat 20 acres Private Pond, 'Small Town Getaway', Tranquility Cottage | 3 Bed, 1.5 Bath, Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats |
Holiday Homes in Winchester
Top Locations for Holiday Homes in Winchester
Top trending hotels in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Countryside Inn & Suites

French Quarter Inn

Beverly hills inn
More ways to explore Winchester
Top picks
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^Subject to availability and chosen travel dates.