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, barbecue grills, and a garden.
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
$122 nightly
The price is $138 total per night
$138 total
Apr 19 - Apr 20
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 dry cleaning/laundry, luggage storage, and securing valuables. 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
$144 nightly
The price is $159 total per night
$159 total
Apr 14 - Apr 15
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. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include a library, express check-out, and a terrace.
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 garden.
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
$110 nightly
The price is $119 total per night
$119 total
Apr 16 - Apr 17
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 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
$96 nightly
The price is $104 total per night
$104 total
May 4 - May 5
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
1204 Berryville Avenue Winchester VA
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $122 total per night
$122 total
Apr 20 - Apr 21
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 securing valuables, luggage storage, and tours or tickets. 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
$100 nightly
The price is $113 total per night
$113 total
Apr 26 - Apr 27
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
111 Hospitality Drive Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $116 total per night
$116 total
Apr 26 - Apr 27
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 dry cleaning/laundry, securing valuables, 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 | 2,081 hotels |
|---|---|
Lowest Price | $104 |
Highest Price | $159 |
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

La Quinta Inn & Suites by Wyndham Winchester
1/5 Terrible
"Mostly everything was satisfactory except the rooms. There was a ceiling to floor window through the wall into the bathroom. It was crazy because if you were sitting on the bed you could see someone in the shower or on the toilet. How does that even make sense. We had to hold up a towel each time someone took a shower or went to the bathroom. I would never stay there again basically for that reason."
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 19 hours ago
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