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Browse for Winchester Winery Hotels from $49

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Top Winchester Winery Hotels

The Ashby Inn & Restaurant
3.5 out of 5
692 Federal St, Paris, VA
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4.8/5Exceptional! (40 reviews)

"Greater at the door as we were exiting our car. Taken on a brief tour of the facilities as we were shown our room. Great way to start our stay. Breakfast the next.morning was delicious. Our server paid just the right amount of attention as I waited for that first cup.of coffee to kick in. Just a ..."…"

Reviewed on Jun 28, 2019

The Ashby Inn & Restaurant
Hotel Strasburg
3 out of 5
213 S. Holliday Street, Strasburg, VA
$107
per night
Feb 18 - Feb 19
3.9/5Very Good! (701 reviews)

"Everything in a hotel was 1800's Decor, Including the building!! Just loved it all!"…"

Reviewed on Dec 4, 2019

Hotel Strasburg
L Auberge Provencale Bed and Breakfast
3.5 out of 5
13630 Lord Fairfax Highway, White Post, VA
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4.7/5Exceptional! (16 reviews)
awesome stay!

"My husband and I celebrated our anniversary here and it was amazing. The staff was great from beginning to end. We enjoyed all the delicious food fro dinner and breakfast. We have decided to make this one of our spots when we need to get away from the kids, city and the everyday hustle."…"

Reviewed on Jul 18, 2016

L Auberge Provencale Bed and Breakfast
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free CancellationReserve now, pay when you stay
$80
per night
Feb 18 - Feb 19
4.3/5Excellent! (1,681 reviews)

"Part of the ceiling decoration (wood panel) was hanging off the ceiling. We mentioned it to the front desk and they changed our rooms immediately."…"

Reviewed on Jan 27, 2020

La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free CancellationReserve now, pay when you stay
$76
per night
Feb 24 - Feb 25
4.5/5Wonderful! (1,767 reviews)

"The staff was really nice and helpful to answer all questions about the area."…"

Reviewed on Feb 15, 2020

Country Inn & Suites by Radisson, Winchester, VA
Royal Inn Motel
2.5 out of 5
533 S. Royal Avenue, Front Royal, VA
Free CancellationReserve now, pay when you stay
$50
per night
Feb 18 - Feb 19
3.2/5 (114 reviews)

"Clean, spacious room. Very courtious staff."…"

Reviewed on Sep 9, 2019

Royal Inn Motel
Super 8 by Wyndham Front Royal
2 out of 5
111 South St, Front Royal, VA
Free CancellationReserve now, pay when you stay
$55
per night
Mar 2 - Mar 3
3.4/5Good! (589 reviews)

"Pet friendly, quiet, reasonable price, room amenities. The free breakfast underwhelms compared to others."…"

Reviewed on Feb 4, 2020

Super 8 by Wyndham Front Royal
Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 out of 5
10 S Commerce Ave, Front Royal, VA
Free CancellationReserve now, pay when you stay
$61
per night
Feb 24 - Feb 25
3.3/5 (402 reviews)

"Perfect location to start Skyline Drive.. The Thai restaurant adjacent in the same building was awesome."…"

Reviewed on Oct 18, 2018

Baymont by Wyndham Front Royal Near Shenandoah National Park
Holiday Inn Express Winchester South-Stephens City
2.5 out of 5
165 Town Run Ln, Stephens City, VA
Free Cancellation
$76
per night
Feb 27 - Feb 28
4.1/5Very Good! (350 reviews)

"We were traveling and needed a great night of rest! This hotel was perfect. Very clean and quiet."…"

Reviewed on Feb 15, 2020

Holiday Inn Express Winchester South-Stephens City
 Quality Inn Stephens City-Winchester South
2.5 out of 5
167 Town Run Ln, Stephens City, VA
Free CancellationReserve now, pay when you stay
$68
per night
Mar 2 - Mar 3
3.9/5Very Good! (295 reviews)

"Great staff and the property is conveniently located just off I-81. Go eat at Paladin, great restaurant about 1/2 mile down the street."…"

Reviewed on Jan 6, 2020

 Quality Inn Stephens City-Winchester South
Budget Inn - Strasburg
2 out of 5
28999 Old Valley Pike, Strasburg, VA
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2.3/5 (3 reviews)

"Pretty run down place, the bathroom sink was clogged and didn't look like anyone took the time to actually clean the room."…"

Reviewed on Dec 2, 2015

Budget Inn - Strasburg
Econo Lodge Inn & Suites
2 out of 5
91 Reliance Road, Middletown, VA
Free CancellationReserve now, pay when you stay
$67
per night
Feb 24 - Feb 25
3.1/5 (156 reviews)
Great place.

"Just needed a place to stay returning from a friends wedding. Hotel was awesome. Good service and apreciated the stay. The mattress was very firm so it was hard to sleep, but other then that a perfect stay."…"

Reviewed on Sep 27, 2019

Econo Lodge Inn & Suites
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
$95
per night
Feb 20 - Feb 21
4.7/5Exceptional! (245 reviews)

"This Inn is very historic and we enjoyed looking at all of the history throughout the building. The staff were very knowledgeable and helpful. The location was very convenient to the battlefield locations we were visiting. In addition, we had a GREAT breakfast that was included in the rate. We also ..."…"

Reviewed on Feb 10, 2020

Wayside Inn
Motel 6 Winchester, VA
2 out of 5
2951 Valley Avenue, Winchester, VA
Free Cancellation
$51
per night
Feb 19 - Feb 20
4/5Very Good! (770 reviews)

"The room was very clean and upgraded. A very quiet nice place to stay. What bothered me a little was u can hear thru the walls pretty good"…"

Reviewed on Feb 1, 2020

Motel 6 Winchester, VA
Motel 6 Front Royal, VA
2 out of 5
141 West 15th Street, Front Royal, VA
Free Cancellation
$49
per night
Feb 20 - Feb 21
3.3/5 (172 reviews)

"It was fine for needing a place to stay and nice that they allow pets at no extra to charge"…"

Reviewed on Dec 6, 2019

Motel 6 Front Royal, VA
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Winchester Winery Hotels

You may know Virginia as the Mother of Presidents, but did you also know it is the birthplace of American wine? Virginia's overall climate and rich soil allow this area to produce award-winning wines. Winchester carries on that history by producing some of the East Coast's best varietals. However, in between toasting with your friends and making new ones you will need a place to stay. Expedia has 563 hotels near wineries, making it convenient to toast, tour, and appreciate Winchester's wine region.

A Winchester Wine Vacation that Hits all the Notes

We have some of the best wine hotels in the country. We have everything from luxury lodgings with pools, spas, and award-winning restaurants to ones that provide just enough of what you need for a relaxing stay. And no matter what hotel you decide on, you can rest assured knowing that you will be welcomed with lots of amenities, a cozy bed, and accommodations not far from Winchester's wineries.

After you check out your room, venture out to some of Winchester's best wineries. If you are unsure where to begin your grape adventure, you can always head to Deer Meadow Vineyard to try their regional varietals. You'll find that many of these wineries are like a close-knit family, and they'll be happy to direct you to some of their favorites in the area. It's true that you can purchase a bottle of wine from your neighborhood store, but tasting local wines while also having the vineyards that produced them as a backdrop is a unique experience.

Reserve a Winchester Winery Hotel Today!

Virginia's rolling countrysides and long history of wine production means this state should be on every wine-lover's list Your Winchester vacation is moments away. We have hotels near wineries ranging from $49 to $107. If you want to find out which lodging might be the best for your Winchester wine tour, then make sure to read through our 7301 reviews. But unlike a fine wine that gets better with age, these deals won't last long. Book soon to get your preferred location for your Winchester grape escape.

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