Find & compare romantic hotels in Winchester, VA from $105

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Top Winchester Romantic Getaways & Hotels

Smithfield Farm B&B

Smithfield Farm B&B

3 out of 5
568 Smithfield Lane, Berryville, VA
Free Cancellation
Reserve now, pay when you stay
The price is $230 per night
$230
per night
May 29 - May 30
A garden, a terrace, and more await visiting couples at this romantic bed & breakfast.
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
per night
Jun 16 - Jun 17
Indulge in a romantic getaway at this Georgian hotel, where you'll find a spa, in-room massages, and a spa tub. Couples will love the 2 restaurants and premium ...
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is $105 per night
$105
per night
Jun 2 - Jun 3
Celebrate with a romantic getaway at this Colonial hotel, where you'll find a garden, happy hours, and a lobby fireplace. You'll also love the romance packages ...
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

2.5 out of 5
1204 Berryville Avenue, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $118 per night
$118
per night
Jun 5 - Jun 6
A garden and premium mattresses await at this romantic hotel, which also offers luxury bedding and a terrace.
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $117 per night
$117
per night
Jun 23 - Jun 24
An outdoor pool and more await visiting couples at this romantic hotel.
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
per night
Jun 2 - Jun 3
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 ...
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4 out of 5
111 Hospitality Drive, Front Royal, VA
Free Cancellation
Reserve now, pay when you stay
The price is $118 per night
$118
per night
Jun 9 - Jun 10
If you're in the mood for love, consider staying at this romantic hotel, featuring a spa tub and happy hours. You'll also love the lobby fireplace, restaurant, ...
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
The price is $106 per night
$106
per night
Jun 2 - Jun 3
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 ...
Hotel Strasburg

Hotel Strasburg

3 out of 5
213 S. Holliday Street, Strasburg, VA
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Indulge in a romantic getaway at this historic hotel, which offers a garden, premium mattresses, and private dining. Couples will love the bar and Victorian ...
Celebration Retreat

Celebration Retreat

5 out of 5
440 Scenic Overlook Dr, Front Royal, VA
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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.
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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.

Winchester hotels essential information

Accommodation
1,858 hotels
Lowest Price
$105
Highest Price
$230
Popular hotels
Celebration Retreat, Smithfield Farm B&B, 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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"I love the country Inn and suites have always chosen this place no matter the location. This location was very clean and the staff was very accommodating. The bed wasn’t the most comfortable, but it was a good stay."
A verified traveler stayed at Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA

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