Book Holiday Homes in Winchester
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Featured Holiday Homes in Winchester
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Lovely 2nd Floor Apartment
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Charming Waterfront Log Cabin
Beautiful, private log cabin with huge, relaxing screened porch
Downtown Hot Tub Escape
Hilltop Home with Great Views
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Spectacular Mountain views with all the amentities nearby
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 | 93 Holiday Homes |
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Lowest Price | AU$161 |
Highest Price | AU$731 |
Popular accommodation | 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Lovely 2nd Floor Apartment, Private Suite with a Sweet View. Spacious, close to town, dog friendly, Charming Waterfront Log Cabin, Beautiful, private log cabin with huge, relaxing screened porch, Downtown Hot Tub Escape, Hilltop Home with Great Views, Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby, Spectacular Mountain views with all the amentities nearby |
More accommodations in Winchester
Top trending hotels in Winchester
The Colonial Hotel
Colonial Motel And Spa
The Covered Bridge Inn
Hampton Inn Brattleboro
More ways to explore Winchester
Top picks
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^Subject to availability and chosen travel dates.