Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Winchester Holiday
Our pick of the best Winchester Hotel Deals
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
The price is NZ$173 per night from 12 Apr to 13 Apr
NZ$173
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Breakfast was excellent and all the staff were very friendly.
Reviewed on 30 Mar 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$208 per night from 15 Apr to 16 Apr
NZ$208
15 Apr - 16 Apr
includes taxes & fees
9.2/10 Wonderful! (2,270 reviews)
Clean room, it’s our second visit and still just as clean as last visit.
Reviewed on 3 Apr 2026
Sleep Inn & Suites Winchester near University
140 Costello Dr Winchester VA
Fully refundable
The price is NZ$160 per night from 9 Apr to 10 Apr
NZ$160
9 Apr - 10 Apr
includes taxes & fees
7.8/10 Good! (1,000 reviews)
I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature
Reviewed on 26 Mar 2026
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.
Explore a world of travel with Expedia
- B&B in Millwood
- Cabin Rentals in Winchester
- Cottages in Winchester
- Motels in Winchester
- B&B in Huntly
- Cottages in Huntly
- Cabin Rentals in Huntly
- Cottages in Hillsboro
- Caravan Parks in Blue Ridge
- B&B in Blue Ridge
- Chalets in Round Hill
- Villas in Paris
- Cabin Rentals in Gore
- Pet Friendly Hotels in Huntly
- Lgbt Welcoming Hotels in Front Royal
- Lgbt Welcoming Hotels in Winchester
- Pet Friendly Hotels in Winchester
- Luxury Hotels in Winchester
- Wyndham Hotels in Gore
- Hilton Hotels in Blue Ridge
- Delaplane Hotels
- White Post Hotels
- Berryville Hotels
- Hotels near Wayside Theater
- Clear Brook Hotels
- Hotels near Front Royal Entrance Shenandoah National Park
- Middletown Hotels
- Hotels near Naked Mountain Winery & Vineyards
- Gore Hotels
- Markham Hotels
- Paris Hotels
- Hotels near Winchester Regional
- Bluemont Hotels
- Boyce Hotels
- Round Hill Hotels
- Hotels near Philip Carter Winery
- Millwood Hotels
- Front Royal Hotels
- Old Town Winchester Hotels
- Strasburg Hotels
- Upperville Hotels
- Linden Hotels
- Winchester Hotels
- Star Tannery Hotels
- Stephens City Hotels
- Hillsboro Hotels
- Huntly Hotels
- Purcellville Hotels
- Flights to Front Royal
- Flights from Blue Ridge
- Flights from Strasburg
- Flights from Winchester
- Flights from Star Tannery
- Flights from Front Royal
- Flights from Cornwall (YCC) to Winchester (WGO)
- Flights from Indianapolis (IND) to Winchester (WGO)
- Flights from Rochester (ROC) to Winchester (WGO)
- Flights from St. Petersburg (PIE) to Winchester (WGO)
- Naked Mountain Winery & Vineyards
- Red Rock Wilderness Overlook Regional Park
- Yogi Bear's Jellystone Park
- Woodstock Tower Observation Site
- Sterling Holidays
- Ashburn Park
- Copper Fox Distillery
- Leesburg Holidays
- Ashburn Holidays
- Nalls Farm Market
- Delaplane Cellars
- Belle Grove Plantation
- Secret Passage Ranch
- Car and Carriage Caravan Museum
- Cobbler Mountain Cellars
- Pearmund Cellars Winery
- Waterford Holidays
- Dulles South Multipurpose Center Skatepark
- The Garden Maze at Luray Caverns
- Cookology Recreational Culinary School
- Philip Carter Winery
- Wayside Theater
- Natural Art Garden Center
- Mary's Rock Summit Trailhead
- Warren Rifles Confederate Museum
- Bogati Bodega & Winery
- Jiffy Lube Live
- Raflo Park
- Belle Boyd Cottage
- Bull Run Country Club
- Visit Stephens City
- Visit Gore
- Visit Cross Junction
- Visit Millwood
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
