Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$162 per night from 8 June to 9 June
NZ$162
8 June - 9 June
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"Staff were on top of everything, very roomy rooms, clean, and the hotel it self was clean. The morning meals was basic but plenty and fresh."
Reviewed on 18 May 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$211 per night from 7 June to 8 June
NZ$211
7 June - 8 June
includes taxes & fees
9/10 Wonderful! (862 reviews)
"There was a smell when we got into the room. Breakfast was good and staff were helpful."
Reviewed on 19 May 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is NZ$251 per night from 2 June to 3 June
NZ$251
2 June - 3 June
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"You can’t go wrong staying here. The staff were very friendly. The beds were very comfortable and the room was very clean. This hotel is centrally located so you can park your car and walk around the old town area. This was our second time staying here and it didn’t disappoint. We will definitely ..."
Reviewed on 17 May 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.
