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

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$138 total

Jun 21 - Jun 22

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

$144 nightly

$159 total

Jun 14 - Jun 15

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

$123 nightly

$133 total

Jun 14 - Jun 15

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

$114 nightly

$129 total

Jun 21 - Jun 22

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

$93 nightly

$106 total

Jul 1 - Jul 2

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

$128 nightly

$141 total

Jun 14 - Jun 15

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

$95 nightly

$103 total

Jul 12 - Jul 13

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 ...

Hotel Strasburg

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

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	2,090 hotels
Lowest Price	$103
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 Winchester hotel reviews by fellow wanderers

The George Washington Hotel, A Wyndham Grand Hotel

4 out of 5

Posted 21 hours ago

Travelocity Verified Review

"The physical structure of this hotel would have put it at 5 stars, but it seems like they have a really nice property here, but don't know how to run it like a really nice hotel. First, the idea that a hotel of this caliber has an UNO pizza as their hotel is just strange. Also, the bar is gorgeous and well appointed, but it closes at 11 PM. Both nights we stayed there, the group wanted to stay longer and visit and buy drinks, but the first night we had to leave at 11 and the second night, following the wedding, there was nowhere to go. Lost opportunity there. Also, many guests we spoke to had problems with their room keys. urs didn't work on our second day there and a maid saw us trying to get it to work and just came over and swiped us in. My husband then went down and got new keys, but we were appreciative but also bothered that she let us in with no ID. Then the worst one was that the groom's parents' keys didn't work after the wedding. SO after 12AM they couldn't get into their room and there was nobody on duty. They had to call the National phone number for Wyndham to get someone to come and then, when someone named Phillip DID come, he was very rude to her. Fix your key problem. I liken the physical building and vibe with Hotel Bethlehem, William Penn, lovely historic hotels, but it sure isn't run with that kind of service."

A verified traveler stayed at The George Washington Hotel, A Wyndham Grand Hotel

La Quinta Inn & Suites by Wyndham Winchester

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"Enjoyed the pool and workout space very much. Everything was very tidy and felt like it was brand new. Typical hotel breakfast with waffles, eggs, bacon as well as the usual cold selection including hard boiled eggs. Excellent coffee in the lobby for our morning departure."

A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester