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Old Town Winchester Vacations

Pack those stellar shades. We have Old Town Winchester vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Old Town Winchester – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Old Town Winchester vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Old Town Winchester

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Old Town Winchester vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Old Town Winchester well.

Old Town Winchester Flight + Hotel packages

Top Hotel Deals

See all 56 Hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester
4.0 out of 5.0

Located in Old Town Winchester, this spa hotel is within a 5-minute walk of Handley Regional Library, Old Court House Civil War Museum, and Bright Box Theater. ...

$107

$107
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd, Winchester
3.0 out of 5.0

Located in Front Royal Entrance, this hotel is within 6 mi (10 km) of Appleland Sports Center, The Kernstown Battlefield, and Shenandoah University. Winchester-Frederick ...

$89

$89
Wingate by Wyndham Winchester

Wingate by Wyndham Winchester

150 Wingate Dr, Winchester
3.0 out of 5.0

Located in Front Royal Entrance, this hotel is within a 10-minute walk of Abram's Delight, Winchester-Frederick County Convention & Visitors Bureau, and Apple ...

$72

$72
La Quinta Inn & Suites Winchester

La Quinta Inn & Suites Winchester

1055 Millwood Pike, Route 50 East, Winchester
3.5 out of 5.0

Located in Front Royal Entrance, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple ...

$82

$82
Hampton Inn Front Royal

Hampton Inn Front Royal

9800 Winchester Rd, Front Royal
2.5 out of 5.0

Located in Front Royal Entrance, this hotel is within 3 mi (5 km) of Blue Ridge Shadows Golf Club, Bing Crosby Stadium, and Belle Boyd Cottage. Warren Rifles ...

$93

$93
Motel 6 Winchester, VA

Motel 6 Winchester, VA

2951 Valley Avenue, Winchester
2.5 out of 5.0

Located in Front Royal Entrance, this motel is 0.6 mi (1 km) from The Kernstown Battlefield and within 3 mi (5 km) of Apple Blossom Mall and Abram's Delight. ...

$55

$55
Ramada Strasburg Va

Ramada Strasburg Va

21 Signal Knob Dr, Strasburg
3.0 out of 5.0

Located in Front Royal Entrance, this hotel is within 1 mi (2 km) of Hupp's Hill Civil War Park and Strasburg Town Hall. Strasburg Museum and Strasburg Theater ...

$65

$65
Holiday Inn Winchester Se-Historic Gateway

Holiday Inn Winchester Se-Historic Gateway

333 Front Royal Pike, Winchester
3.0 out of 5.0

Located in Front Royal Entrance, this hotel is 1.1 mi (1.7 km) from Shenandoah University and within 3 mi (5 km) of Apple Blossom Mall and Jim Barnett Park. ...

$93

$93
Travelodge - Winchester

Travelodge - Winchester

160 Front Royal Pike, Winchester
2.5 out of 5.0

Located in Front Royal Entrance, this motel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple ...

$49

$49
Super 8 Winchester VA

Super 8 Winchester VA

1077 Millwood Pike, Winchester
2.5 out of 5.0

Located in Front Royal Entrance, this motel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple ...

$51

$51

Top Flight Deals

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