Romantic Hotels in Winchester, VA

Name: DoubleTree by Hilton Front Royal Blue Ridge Shadows
Price range: $108 total

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Dec 23 - Dec 24

Tonight

Dec 24 - Dec 25

Tomorrow night

Featured Winchester Romantic Getaways & Hotels

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 garden, and a picnic area.

Kitchen

Pet friendly

The George Washington Hotel, A Wyndham Grand Hotel

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$143 total

Dec 29 - Dec 30

Total with 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 securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this spa hotel include free WiFi in public areas, conference space, and a business center.

Pool

Spa

$89 nightly

$98 total

Dec 24 - Dec 25

Total with taxes and fees

Wayside Inn features free WiFi in public areas, coffee in a common area, and a meeting room. You can take advantage of free parking if you drive. Additional amenities include a library, express check-out, and a terrace.

Parking included

Free WiFi

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, a TV in a common area, and a garden.

Breakfast included

Pet friendly

La Quinta Inn & Suites by Wyndham Winchester

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$107 total

Dec 25 - Dec 26

Total with 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 dry cleaning/laundry and luggage storage. Additional amenities include meeting rooms, a business center, and express check-out.

Pool

Breakfast included

Country Inn & Suites by Radisson, Winchester, VA

Free Cancellation

$83 nightly

$90 total

Jan 18 - Jan 19, 2026

Total with 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

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$120 total

Dec 29 - Dec 30

Total with 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 tours or tickets, securing valuables, and luggage storage. 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

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$115 total

Jan 4 - Jan 5, 2026

Total with 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 dry cleaning/laundry and luggage storage. 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

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 total

Dec 29 - Dec 30

Total with 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 luggage storage, concierge services, and dry cleaning/laundry. Other amenities at this golf hotel include free WiFi in public areas, a hot tub, and a conference center.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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 Winchester

Can'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	2,026 hotels
Lowest Price	$90
Highest Price	$143
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