Book Holiday Homes in Winchester
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Featured Holiday Homes in Winchester

Cozy Home Near Downtown, Shops, and Restaurants.

The Jelly Mill-A River Retreat

1810 Brook Side Mill/House / EV Level 2 Charging on Site

GAMERS HAVEN, River Wine Inn!

Family Friendly Hilltop House In Putney Vermont

Bright three-level home with water views, jetted tub, firepit, and pool table

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Lovely 2nd Floor Apartment

Beautiful Lakefront home - perfect getaway for every season!
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 | 117 Holiday Homes |
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Lowest Price | AU$162 |
Highest Price | AU$949 |
Popular accommodation | Cozy Home Near Downtown, Shops, and Restaurants., The Jelly Mill-A River Retreat, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, GAMERS HAVEN, River Wine Inn!, Family Friendly Hilltop House In Putney Vermont, Bright three-level home with water views, jetted tub, firepit, and pool table, Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck, Lovely 2nd Floor Apartment, Beautiful Lakefront home - perfect getaway for every season! |
Top trending hotels in Winchester

The Colonial Hotel

Hampton Inn Brattleboro

Colonial Motel And Spa

The Putney Inn
More ways to explore Winchester
Top picks
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^Subject to availability and chosen travel dates.