Winchester Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Winchester

“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking

1 Bed/1 Bath Guest House

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

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

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!

Unique and secluded A frame home on 31 acres with hot tub.

Sunset Cabin-Adults Only Hot Tub Getaway

Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake

Grain Bin - Unique Stay

Family Farm Retreat: 2 Homes + Private Pond, Minutes to Rocky Fork Lake
Holiday Accommodation Winchester
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Winchester are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Winchester itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Winchester holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Winchester, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Winchester with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Winchester Holiday Homes essential information
Accommodation | 41 Holiday Homes |
|---|---|
Lowest Price | NZ$108 |
Highest Price | NZ$1,301 |
Popular accommodation | “Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking, 1 Bed/1 Bath Guest House, Spacious 4-bedroom 19th Century home in historic downtown Maysville!, McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events, LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!, Unique and secluded A frame home on 31 acres with hot tub., Sunset Cabin-Adults Only Hot Tub Getaway, Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake, Grain Bin - Unique Stay, Family Farm Retreat: 2 Homes + Private Pond, Minutes to Rocky Fork Lake, Historic Tin Shop – 3BR/3BA Wedding & Family Retreat, Blue Creek Hunting Retreat 3BR/2BA Near Shawnee State Forest |
Top trending hotels in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
^Eligibility requirements and conditions apply









