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Cheap Vacations in Winchester

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Winchester Vacation Deal FAQ's

Where to find Winchester package deals?

On CheapTickets, you can find package deals in Winchester as low as !

When is peak season in Winchester?

July, June, May are very popular times to visit Winchester.

When is the best time to visit Winchester?

If you're looking for cheap vacations to Winchester, April is the best time to visit Winchester.

When is the worst time time to visit Winchester?

Prices for Winchester vacations can peak during September.

When is low season in Winchester?

We have found January, November, December to be the least-crowded time of the year to visit Winchester.

Where is Winchester?

Looking for an excuse to pack your suitcase and go traveling? Exciting adventures that won't break the bank are waiting for you in Winchester.

It is located 19 miles to the north-east of Strasburg, and 62 miles to the west of Washington, the nation's capital.

Approximately 26,200 people live in this part of Frederick County, so there are loads of opportunities to make some new friends.

Cheap Things to do in Winchester

Forget about entry fees, ticket prices and costly attractions! With our suggestions for free things to do in or near Winchester, you'll be ahead of the curve with some of the best free travel hacks:

  • Looking for somewhere that satisfies your desire for outdoor fun and costs zero, zip, zilch? Look no further than Jim Barnett Park. This place will keep you amused and entertained at the right price.
  • Money-conscious history lovers need to add the Shenandoah University, Mt Hebron Cemetery and the Kernstown Battlefield to their vacation hit lists. These historic attractions also offer superb photo opportunities!
  • If you're in the area, we definitely recommend stopping by the Handley Regional Library.

Cheap Winchester Vacation Package Deals

Don't lose sleep over tracking down the best prices on accommodations, flights and incredible experiences. CheapTickets has figured it out for you, and we definitely haven't made compromises on convenience or quality.

Up for saving as much as $290^? Just combine your hotel and airfare bookings. With 500 partner airlines and 500,000 properties globally, you have a world of choice just a couple of clicks away.

Here at CheapTickets, we're serious when we say we want to save you a tidy sum. If you find a better price within 48 hours of purchasing your package, we'll match that offer and reimburse the difference. It's our Price Guarantee!

Get CheapCash

Just like you, we love all things cheap. That's why we've created our simple rewards program. All you've got to do is book flights and we'll reward you with amazing savings on eligible CheapTickets hotels.

It's amazingly easy to log in or sign up for free and join CheapCash. Once you're up and running there'll be no stopping you! You'll gain savings on eligible bookings, not to mention the perks and bonus offers that will come your way.

Cheap Car Rentals in Winchester

Hey there bargain hunters, want to hear about a comfortable and convenient way of getting from A to B in Winchester? Why not think about hiring a car? Filling up your gas tank every so often has to be easier on your bank balance than dishing out dollars for cabs!

Is the city your first stop? Thrifty can be found 1 mile from the middle of town at WINCHESTER - JUBAL EARLY PLAZA, VA TSH 57 WEST JUBAL EARLY DRIVE. Enterprise is another fantastic option available to you. It is positioned at 2711 VALLEY AVE, only 2 miles from the center of town.

Cheap Hotels in Winchester

CheapTickets presently lists 22 hotels in Winchester. Score one of the top options so you can start planning the rest of your cheaptastic getaway.

The George Washington Hotel, A Wyndham Grand Hotel and the Wingate by Wyndham Winchester are fabulous places to crash in this area.

Flight deals to Winchester

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jan 28
MCO
Orlando
BWI
Baltimore
$23
Spirit Airlines
Sat, May 15
DEN
Denver
BWI
Baltimore
$27
Frontier Airlines
Fri, Feb 12
MCO
Orlando
DCA
Washington
$31
JetBlue Airways
Thu, Feb 18 - Fri, Feb 19
MCO
Orlando
BWI
Baltimore
$46
Spirit Airlines
Wed, Mar 10 - Tue, Mar 16
BOS
Boston
BWI
Baltimore
$48
Spirit Airlines
Sun, May 23 - Wed, May 26
MCO
Orlando
DCA
Washington
$61
JetBlue Airways

Top rated hotels for your Winchester vacation

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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.