Book Holiday Homes in Winchester
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Featured Holiday Homes in Winchester
Two Bare Feet
Lovely dog friendly 2 bed bungalow with parking
Squirrels Drey
Beautiful 2-bed Apart in Southampton
Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks
Unique waterside home in stunning location.
Spacious semi-detached Southsea House
Luxury home in the New Forest featuring a year-round heated swimming pool.
Rampart View - a house that sleeps 6 guests in 3 bedrooms
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 | 462 Holiday Homes |
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Lowest Price | NZ$192 |
Highest Price | NZ$211 |
Popular accommodation | Two Bare Feet, Lovely dog friendly 2 bed bungalow with parking, Squirrels Drey, Beautiful 2-bed Apart in Southampton, Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks, Unique waterside home in stunning location., Spacious semi-detached Southsea House, Luxury home in the New Forest featuring a year-round heated swimming pool., Rampart View - a house that sleeps 6 guests in 3 bedrooms |
Top trending hotels in Winchester
The Winchester Hotel & Spa
Winchester Royal Hotel
Norton Park Hotel, Spa & Manor House
Mercure Wessex Winchester Hotel
More ways to explore Winchester
Top picks
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^Subject to availability and chosen travel dates.