Book Holiday Homes in Winchester
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Featured Holiday Homes in Winchester

S'mores & More Tiny House - Tracy City

Mountain Point of View Cottage - 15 Minutes from the Caverns!

Robert's Manor - A Historical Home from 1880s

Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall

Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

Caverns,Sewanee,Waterfalls,Fall Hike:Tiny Basecamp

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

Mountain Memories to provide a cozy retreat on your vacation!

Beautiful Monteagle Bluff Mountain Home Sleeps 12
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 | 306 Holiday Homes |
|---|---|
Lowest Price | NZ$97 |
Highest Price | NZ$1,023 |
Popular accommodation | S'mores & More Tiny House - Tracy City, Mountain Point of View Cottage - 15 Minutes from the Caverns!, Robert's Manor - A Historical Home from 1880s, Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall, Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!, Caverns,Sewanee,Waterfalls,Fall Hike:Tiny Basecamp, Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall! , Mountain Memories to provide a cozy retreat on your vacation!, Beautiful Monteagle Bluff Mountain Home Sleeps 12 |
Top trending hotels in Winchester

Best Western Inn

Beautiful Lake Views at Twin Creeks!

The Smokehouse Lodge and Cabins

Microtel Inn & Suites by Wyndham Manchester
More ways to explore Winchester
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
