Winchester Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Winchester

Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winchester Vacation Rentals essential information

Accommodation
91 Vacation Rentals
Lowest Price
$174
Highest Price
$489
Popular accommodation
Quaint ranch home with chic finishes & large patio/yard, Tranquil Pet-Friendly Cottage Retreat on 42 Acres at Lost Pines Shire, TuscanyNTexas, Charming Victorian Bike to Shops, Mins to Antiques & Wedding Venues, Short cottage, Serene Pet-Friendly Vacation Rental in the 42 Acre Lost Pines Shire, Riverside Romance/Luxury RV/Starry Skies & S'mores, LARGE PARTY LUXURY, AND YOU CHOOSE YOUR SPACE AND PRICING, The Ramona House w/ Cowboy Pool! Walk to Downtown!, Charming & Cozy Victorian in Quiet Residential Setting, Pine Top View with the Club House, Sauna, Pool, Enchanting Casita, 5 minutes to Round Top!