Search Winchester Holiday Homes from AU$114
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Featured Holiday Homes in Winchester

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

On the river ~ hot tub ~ serene river views ~ fire pit

Secluded 3-bedroom, 2-loft lakefront house in private Sleepy Hollow community.

Hot Tub, Fire Pit, Grill, Screened Porch & WiFi

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Cozy Lakeside Homestead

The Apple Mountain House

Woods Song - Hot Tub | Fireplace | Golf | Pool Pass | Woods Resort | Grill

Upscale Harpers Ferry Getaway
Holiday Accommodation Winchester
Get the Lowdown on Winchester Holiday Homes
How much is a holiday home in Winchester?
Depending on when you visit, you can score a holiday home in Winchester for as little as AU$114 per night. Prices vary by property class, amenities, and location, all of which you can quickly sort through on our handy search page.
How do I find the best price for a holiday home in Winchester?
Discover exclusive deals on Winchester house rentals when you book with Wotif. Once you enter the dates of your trip and number of travellers (Girls’ trip? Family getaway? We’ve got you covered.), filter the results by guest rating, budget, property class, number of bedrooms, amenities, and more. You can also use the map feature to zoom in on the neighbourhood or to view several rentals at once.
Why should I book a holiday home in Winchester?
Because there’s nothing better than having a private place to call your home away from home while exploring Winchester. When you book a holiday house in Winchester, you can indulge in a variety of sweet amenities and truly relax in your own space.
What is the best time to stay in a holiday home in Winchester?
Pack your bags and head to your rental house in , the most popular time to visit. If smaller crowds are your thing, book a holiday home in the off-season, around , when you may get more of a bargain.
How many holiday homes are available for rent in Winchester?
Whether you’re adventuring to Winchester for the first time or planning a return trip to your favourite spot, pick from 619 unique holiday homes in Winchester.
What amenities are available in a private holiday home?
You’ll often find most amenities you’re looking for, such as a private pool or hot tub, parking on the premises, a full-service kitchen or kitchenette, laundry and Wi-Fi. If your companion has four legs, book a pet-friendly Winchester accommodation so your furry pal is as comfy and cosy as can be. Keep in mind that the price of your rental will depend on how luxe the amenities are.
Why should I book a holiday home with Wotif?
You’ll find spectacular deals, book now and pay later discounts, and a massive inventory of one-of-a-kind house rentals. Save big bucks when you book your Winchester car hire and accommodation together into a Winchester holiday package. Our Price Promise means that if you find a lower price online up to 24 hours before check-in, we’ll match it and refund the difference. Do the right thing and book your Winchester holiday house with Wotif.
What are the cancellation and flexibility options?
We understand that plans change, so we offer thousands of holiday homes that have free cancellations. To be sure your rental can be cancelled for a full refund, filter your search by “free cancellation”. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.
Winchester Holiday Homes essential information
Accommodation | 619 Holiday Homes |
|---|---|
Lowest Price | AU$114 |
Highest Price | AU$951 |
Popular accommodation | Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, On the river ~ hot tub ~ serene river views ~ fire pit, Secluded 3-bedroom, 2-loft lakefront house in private Sleepy Hollow community., Hot Tub, Fire Pit, Grill, Screened Porch & WiFi, Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!, Cozy Lakeside Homestead, The Apple Mountain House, Woods Song - Hot Tub | Fireplace | Golf | Pool Pass | Woods Resort | Grill, Upscale Harpers Ferry Getaway, Welcome to The Basye Swan, Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres! |
Top trending hotels in Winchester

Travelodge by Wyndham Winchester
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