Find Romantic Hotels in Winchester, VA

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Pick from 14 Winchester Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Smithfield Farm B&B
Exterior
Smithfield Farm B&B
3.0 star property
9.4 out of 10, Exceptional, (90)
"Beautiful property, beautiful farm and great old House. Farm store right next by was great also. However, no TV in our room and the TV downstairs wasn’t working, also no WiFi at all. I understand getting away from it all in the beautiful country, but to have no internet was disappointing. The breakfast was made and left in fridge before we arrived. It was a tasty plate of cold cuts, fruit , cheeses. A nice hot breakfast featuring eggs and meats from their farm would have been a lot more fun. ...
The price is SAR 815
SAR 899 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Smithfield Farm B&B
The George Washington Hotel, A Wyndham Grand Hotel
Exterior
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1007)
"Wonderful location and very comfortable beds"
The price is SAR 469
SAR 532 total
includes taxes & fees
16 Jum. II - 17 Jum. II
The George Washington Hotel, A Wyndham Grand Hotel
Wayside Inn
Exterior
Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (343)
"Nice quiet inn in a historic setting. "
The price is SAR 394
SAR 434 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Wayside Inn
Hampton Inn Winchester N/Conference Center, VA
Exterior
Hampton Inn Winchester N/Conference Center, VA
2.5 star property
9.2 out of 10, Wonderful, (671)
"This hotel is conveniently located, easy to find and the staff is pleasant. The facility is well maintained, clean and comfortable. "
The price is SAR 411
SAR 466 total
includes taxes & fees
16 Jum. II - 17 Jum. II
Hampton Inn Winchester N/Conference Center, VA
La Quinta Inn & Suites by Wyndham Winchester
Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1359)
"Excellent stay"
The price is SAR 435
SAR 474 total
includes taxes & fees
9 Jum. II - 10 Jum. II
La Quinta Inn & Suites by Wyndham Winchester
Hampton Inn Winchester-University/Mall Area
Pool
Hampton Inn Winchester-University/Mall Area
2.5 star property
9.0 out of 10, Wonderful, (984)
"Very nice and quiet"
The price is SAR 411
SAR 466 total
includes taxes & fees
9 Jum. II - 10 Jum. II
Hampton Inn Winchester-University/Mall Area
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Exterior
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
9.0 out of 10, Wonderful, (1001)
"Wonderfully hotel, wonderful stay"
The price is SAR 443
SAR 500 total
includes taxes & fees
16 Jum. II - 17 Jum. II
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Country Inn & Suites by Radisson, Winchester, VA
Lobby
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1001)
"Nice location with chain restaurants nearby. Traffic noise is loud in the room. "
The price is SAR 411
SAR 447 total
includes taxes & fees
9 Jum. II - 10 Jum. II
Country Inn & Suites by Radisson, Winchester, VA
Hotel Strasburg
Building design
Hotel Strasburg
3.0 star property
7.8 out of 10, Good, (731)
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
Hotel Strasburg
Celebration Retreat
Billiards
Celebration Retreat
5.0 star property
Celebration Retreat
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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.

Frequently asked questions

Searching for romantic hotels in Winchester?
If you and your partner need a romantic escape, we’d like to help you plan for it. Couples choose Winchester for its scenic landscape and top-notch restaurants. If you’re hoping to explore some cultural attractions while you’re in town, Bright Box Theater or Winchester Little Theater make for a fun date night. Whether you’d like to lounge around in luxurious bedding or get a couples’ massage, you’ll be sure to find accommodation in Winchester to make for a relaxing weekend away.
How many romantic hotels are there in Winchester?
Expedia has 5 romantic Winchester hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Winchester?
If you’re looking forward to lots of outings with your partner, check out these details about year-round temperatures in Winchester: The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What is there to do in Winchester?
There’s nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Winchester. If you’re hoping to see some of the area’s cultural attractions, you and your partner will love Winchester for its interesting historical sites and major shopping area. You might think about stopping by Shenandoah Valley Discovery Museum, Museum of the Shenandoah Valley, or Jim Barnett Park while you’re seeing the sights.
What's the best way to get to Winchester and around town during my romantic getaway?
This information about transportation options in Winchester might help your romantic trip get off to a smooth start: If you’re looking to fly to Winchester, the closest major airport is Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city center. If you’d like to venture out around the area, you may want to rent a car for your trip.

Recent reviews of Winchester hotels
Expedia verified reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

5/5 Excellent
"Wonderful location and very comfortable beds"
A verified traveler stayed at The George Washington Hotel, A Wyndham Grand Hotel
Posted 3 days ago
The George Washington Hotel, A Wyndham Grand Hotel