Romantic Hotels in Winchester, VA
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Featured Winchester Romantic Getaways & Hotels

Celebration Retreat
440 Scenic Overlook Dr, Front Royal, VA
This vacation home features free WiFi in public areas, spa services, and a terrace. There's free parking, and an airport shuttle (available 24 hours) for USD 150.00 per vehicle roundtrip. Staff members are on hand to provide concierge services and luggage storage. Other amenities at this luxury vacation home include laundry facilities, a picnic area, and barbecue grills.
Kitchen
Pet friendly

The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $144 total per night
$144 total
Jul 27 - Jul 28
Total includes taxes and fees
At The George Washington Hotel, A Wyndham Grand Hotel, guests enjoy a full-service spa, an indoor pool, and a 24-hour gym. Valet parking is available for USD 15 per night. Front-desk staff can answer questions 24/7, and assist with luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this spa hotel include free WiFi in public areas, conference space, and a business center.
Pool
Spa

Wayside Inn
7783 Main St, Middletown, VA
$114 nightly
The price is $126 total per night
$126 total
Jul 21 - Jul 22
Total includes taxes and fees
Guests of Wayside Inn enjoy free WiFi in public areas, a meeting room, and a library. You can take advantage of free parking if you drive. Additional amenities include a terrace, a ballroom, and a picnic area.
Parking included
Free WiFi

Hotel Strasburg
213 S. Holliday Street, Strasburg, VA
Hotel Strasburg features free WiFi in public areas, conference space, and coffee in a common area. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Other amenities at this historic hotel include free newspapers, wedding services, and a TV in a common area.
Breakfast included
Pet friendly

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $126 total per night
$126 total
Jul 22 - Jul 23
Total includes taxes and fees
At La Quinta Inn & Suites by Wyndham Winchester, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with luggage storage and dry cleaning/laundry. Additional amenities include meeting rooms, a business center, and express check-out.
Pool
Breakfast included

Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
$99 nightly
The price is $108 total per night
$108 total
Jul 22 - Jul 23
Total includes taxes and fees
At Country Inn & Suites by Radisson, Winchester, VA, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a 24-hour business center, and a library.
Pool
Breakfast included

Hampton Inn Winchester N/Conference Center, VA
1204 Berryville Avenue, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $134 total per night
$134 total
Jul 25 - Jul 26
Total includes taxes and fees
At Hampton Inn Winchester N/Conference Center, VA, guests have access to a gym, free WiFi in public areas, and meeting rooms. If you drive, put free parking to good use. The front desk has multilingual staff on hand 24/7 to help with luggage storage, tours or tickets, and securing valuables. Additional amenities include a conference center, a 24-hour business center, and a seasonal outdoor pool.
Pool
Breakfast included

Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $111 total per night
$111 total
Jul 27 - Jul 28
Total includes taxes and fees
At Hampton Inn Winchester-University/Mall Area, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has staff standing by to help with luggage storage and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Breakfast included

DoubleTree by Hilton Front Royal Blue Ridge Shadows
111 Hospitality Drive, Front Royal, VA
Free Cancellation
Reserve now, pay when you stay
$124 nightly
The price is $136 total per night
$136 total
Jul 27 - Jul 28
Total includes taxes and fees
At DoubleTree by Hilton Front Royal Blue Ridge Shadows, guests enjoy a golf course, an indoor pool, and a 24-hour gym. Free parking is included with your stay. Multilingual staff at the 24-hour front desk can assist with securing valuables, concierge services, and luggage storage. Other amenities at this golf hotel include free WiFi in public areas, a hot tub, and a conference center.
Pool
Hot Tub
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.
Couples getaways in Winchester
Time out with your partner in a fancy abode. Meals by candlelight and sparkling Champagne. Sounds like a dream, don't you think? If you're in the mood for a romantic break, organize your escape in Winchester. It's the perfect location for doting couples.
Romantic places to visit in WinchesterCan't wait to head out and make beautiful new memories with your loved one? Check out these romantic attractions that make for the perfect date:
- Looking to take your darling someplace new while you're in town? A trip to Twin Oaks Tavern Winery is bound to impress!
- Another place worth noting on your itinerary is Dickey Ridge Trail. Many lovebirds enjoy their time there together.
- Why not take a look around Cheester Gap Cellars while you're hanging out in the area? It's very popular with tourists and locals alike.
- Finally, if you've got some spare time, you and your loved one really ought to swing by 612 Vineyard.
Winchester hotels essential information
Accommodation | 1,999 hotels |
---|---|
Lowest Price | $108 |
Highest Price | $144 |
Popular hotels | Celebration Retreat, The George Washington Hotel, A Wyndham Grand Hotel, Wayside Inn, Hotel Strasburg, La Quinta Inn & Suites by Wyndham Winchester, Country Inn & Suites by Radisson, Winchester, VA, Hampton Inn Winchester N/Conference Center, VA, Hampton Inn Winchester-University/Mall Area, DoubleTree by Hilton Front Royal Blue Ridge Shadows |
Recent Romantic Getaways & Hotels Reviews

Country Inn & Suites by Radisson, Winchester, VA
5/5 Excellent
"Excellent"
A verified traveler stayed at Country Inn & Suites by Radisson, Winchester, VA
Posted 23 hours ago
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