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

The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
$127 nightly
The price is $144 total per night
$144 total
Oct 5 - Oct 6
Total with taxes and fees
Indulge in a romantic getaway at this Georgian hotel, where you'll find a spa, in-room massages, and premium mattresses. Couples will love the 2 restaurants ...

Wayside Inn
7783 Main St, Middletown, VA
$109 nightly
The price is $120 total per night
$120 total
Oct 28 - Oct 29
Total with taxes and fees
Celebrate with a romantic getaway at this Colonial hotel, where you'll find a garden, a lobby fireplace, and romance packages. You'll also love the private picnics ...

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $118 total per night
$118 total
Oct 5 - Oct 6
Total with taxes and fees
Rekindle the spark in your relationship. Book a romantic getaway at this hotel where you and your special someone are sure to love the Egyptian cotton sheets ...

Hampton Inn Winchester N/Conference Center, VA
1204 Berryville Avenue, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $124 total per night
$124 total
Oct 5 - Oct 6
Total with taxes and fees
A garden and premium mattresses await at this romantic hotel, which also offers luxury bedding and a terrace.

Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $104 total per night
$104 total
Oct 5 - Oct 6
Total with taxes and fees
An outdoor pool and more await visiting couples at this romantic hotel.

DoubleTree by Hilton Front Royal Blue Ridge Shadows
111 Hospitality Drive, Front Royal, VA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $133 total per night
$133 total
Oct 26 - Oct 27
Total with taxes and fees
If you're in the mood for love, consider staying at this romantic hotel, featuring a hot tub and happy hours. You'll also love the lobby fireplace, restaurant, ...

Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
$91 nightly
The price is $99 total per night
$99 total
Oct 26 - Oct 27
Total with taxes and fees
If you're looking for a special getaway, consider a stay at this romantic hotel where there's a lobby fireplace and much more for you and your partner to ...

Celebration Retreat
440 Scenic Overlook Dr, Front Royal, VA
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. You'll appreciate the area shuttle, terrace, and garden.
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.
Winchester hotels essential information
Accommodation | 2,007 hotels |
---|---|
Lowest Price | $99 |
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 Winchester hotel reviews by fellow wanderers

The George Washington Hotel, A Wyndham Grand Hotel
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!"
A verified traveler stayed at The George Washington Hotel, A Wyndham Grand Hotel
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