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Cheap Holidays to Winchester

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Your next trip to Winchester with ebookers

  • Browse our 2021 holiday package deals today! They feature hotels and flights or cars at discounted bundled rates. Book your perfect trip all in one place!
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  • We offer free cancellation on most hotels in case you need to change your plans*

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*Some hotels require you to cancel at least 24-48 hours before check-in. Details on site.

Top deals for trips to Winchester

Baltimore Plaza Inner Harbor
Hyatt Place Baltimore Inner Harbor
Wingate by Wyndham Baltimore BWI Airport
Microtel Inn & Suites by Wyndham BWI Airport Baltimore
Country Inn & Suites by Radisson, BWI Airport (Baltimore), MD

Winchester Holiday Packages for 4 Nights

Baltimore Plaza Inner Harbor
Hyatt Place Baltimore Inner Harbor
Wingate by Wyndham Baltimore BWI Airport
Microtel Inn & Suites by Wyndham BWI Airport Baltimore
Country Inn & Suites by Radisson, BWI Airport (Baltimore), MD

Winchester Holidays

Ready to rejuvenate yourself with a touch of Winchester magic? The hard-working team at ebookers are wizards when it comes to converting travel fantasies into precious memories.

You want your dinner served by the rooftop pool? That's no problem at all. With over 500 airline partners and more than 500,000 international properties to browse though, the world is truly your oyster.

Does a Price Guarantee sound good to you? If you happen upon a cheaper Flight + Hotel deal somewhere else within 48 hours pre check in, we'll meet it and repay the difference.

From bustling cities to the most serene hideaways, there are limitless stories and adventures waiting for you in every corner of the planet. Now is the perfect moment to pack up your bags and get going.

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Holidays in Winchester

Winchester is packed with things to see and experience. The most difficult part of planning your trip will be choosing which to enjoy first!

The population of this city is 26,000.

This destination is situated 120 miles from the state capital, Richmond, and 7 miles from Brucetown.

If you love your wine, don't overlook the opportunity to treat your taste buds at the Bluemont Vineyard and the Chester Gap Cellars. The Glen Manor Vineyards and the Veramar Vineyard are two other popular stops where you can get a more intimate understanding of the region's wine industry.

Skyline Caverns and Jim Barnett Park are some of the best places to bask in the sun, go for a picnic or just watch life pass by. There's also a good deal of fun to be had at State Arboretum of Virginia and Cedar Creek and Belle Grove National Historical Park.

Want to know about upcoming events, tours, local hotspots or kid-friendly outings? Winchester Visitors Center and Dickey Ridge Visitor Center are excellent resources for any questions you have about your stay.

Put on some sensible shoes and pack some snacks. It's time for a day of adventure out in nature at Dickey Ridge Trail.

Wander the halls and admire the marvellous collections at the Museum of the Shenandoah Valley. You're bound to find something which sparks your curiosity.

Exhibiting a selection of exciting science innovations, Mackintosh Fruit Farm offers everything you need to keep your mind buzzing.

Grab a hot cup of coffee and spend the afternoon gallery hopping between the Duvall Designs Gallery and the Fire House Gallery. Boasting a wide array of carefully curated pieces, these popular exhibits offer something for everyone.

Do you want to explore a few history-filled attractions? An excursion to the Shenandoah University or Belle Grove Plantation offer a fascinating glimpse into Winchester's bygone times. Stonewall Jackson's Headquarters and George Washington's Office are also worth a visit.

Indulge in some soul-searching or just quietly absorb the stillness of Holy Cross Abbey, a historic spiritual space.

You might swing by Apple Blossom Mall wanting to grab some essential supplies, but you'll probably walk out with quite a good deal more than that.

Check what's on at the Winchester Little Theater, because there's nothing quite like seeing a spectacular show. Wayside Theater is another top venue if you're up for more.

Don't mind a little healthy competition? Then slip on your best golf glove and challenge some friends to a round at Virginia National Golf Club.

They mightn't be the first things you put on your must-see list, but the Handley Regional Library and the Barns of Rose Hill are still well worth an outing. Don't forget to stop by Rocking S Ranch and Watermelon Park Campground either.

Best Winchester hotel deals for your holiday

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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.

Cheap flights to Winchester

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Top things to do in Winchester

^Savings based on all package bookings with Flight + Hotel made on ebookers.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.