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Our top choices for Winchester hotels with winery

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
"Very nice breakfast (eggs sausage, potatoes, ...), clean lobby, and all the staff was friendly, including Beatrix. Also we appreciated the attention to a clean and warm pool room on a very cold January. Great mexican 1 mile away at Potrillo's."
United States
kenneth
The price is £81
includes taxes & fees
15 Mar - 16 Mar
Hampton Inn Front Royal

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"Awesome hotel, highly recommend. Great staff!"
United States
WILLIAM
The price is £65
includes taxes & fees
22 Mar - 23 Mar
Holiday Inn Winchester Se-Historic Gateway by IHG

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (423 reviews)
"Room 14 was great for spirit activity as well as the rest of the property! Highly recommend ghost hunters to explore the inn. Food at their Larick’s tavern was delish!! Overall service and staff were knowledgeable and friendly! We had a great experience for our anniversary! "
United States
Megan
The price is £66
includes taxes & fees
23 Feb - 24 Feb
Wayside Inn

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (813 reviews)
"Great stay!"
United States
Rene
The price is £86
includes taxes & fees
8 Mar - 9 Mar
SpringHill Suites by Marriott Winchester

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (29 reviews)
"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."
United States
Tom C.
The price is £179
includes taxes & fees
23 Feb - 24 Feb
Blue Mountain Cabin, secluded, perfect for couples, near main road

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (1 review)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is £124
includes taxes & fees
2 Mar - 3 Mar
Luxury tiny home farm stay on historic property with hot tub in Stephens City

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (28 reviews)
"The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience."
United States
Jennifer d.
The price is £312
includes taxes & fees
22 Feb - 23 Feb
Mountain cabin near national park & wineries

The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River
Front Royal
10.0 out of 10, Exceptional, (15 reviews)
"We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!"
United States
Dan P.
The price is £311
includes taxes & fees
9 Mar - 10 Mar
The Vue - Mountain Top hot tub overlooking the Shenandoah River

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (930 reviews)
"Nice staff "
United States
Anthony
The price is £48
includes taxes & fees
8 Mar - 9 Mar
Baymont by Wyndham Front Royal Near Shenandoah National Park

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is £177
includes taxes & fees
23 Feb - 24 Feb
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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.

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Top Winchester Hotel Reviews

Frequently asked questions

How much does a winery hotel in Winchester cost?
Enjoy staying in a winery hotel in Winchester, with plenty of hotels from £48 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during the weekend or around public holidays.
Which area of Winchester is best to stay in for vineyards and wineries?
The beautiful countryside surrounding Winchester, Virginia, is a haven for wine enthusiasts, making it an ideal destination for those seeking a memorable vineyard experience. The area is renowned for its stunning landscapes dotted with picturesque wineries, such as the acclaimed Veramar Vineyard and the charming Willowcroft Farm Vineyards. Staying in the nearby Shenandoah Valley provides convenient access to these delightful locations, where you can indulge in tastings and vineyard tours.

For couples planning a romantic escape, the quaint town of Middleburg, just a short drive from Winchester, offers an idyllic setting. This charming village is home to several boutique wineries and has a lovely selection of gourmet restaurants, superb for a candlelit dinner after a day of wine tasting. The rustic elegance of the countryside creates a superb backdrop for romantic strolls through vineyards or leisurely picnics on the estate grounds.

Families will appreciate the educational aspect of winery visits in this region. Many vineyards offer family-friendly activities, including grape stomping and vineyard tours, which can be an engaging experience for children and adults alike. The scenic views and outdoor spaces provide ample opportunities for family bonding and relaxation amidst nature.
Are there hotels in Winchester near winery tours?
Yes, there are great hotels in Winchester that are close to winery tours, including the SpringHill Suites by Marriott Winchester and the Holiday Inn Winchester Se-Historic Gateway by IHG.

The SpringHill Suites by Marriott Winchester is a fantastic choice, boasting a stellar review rating of 9.4. This hotel offers comfortable rooms and a friendly atmosphere, making it a great base for your wine adventures. With its excellent location, you'll find winery tours nearby, and you can enjoy free Wi-Fi and a complimentary continental breakfast to start your day right.

Another option is the 3-star Holiday Inn Winchester Se-Historic Gateway by IHG, which has an excellent review rating of 9.0. This hotel is also conveniently located near winery tours and features clean, well-maintained rooms.
What winery activities should we do in Winchester?
Winchester, Virginia, is a delightful destination for wine enthusiasts seeking a blend of scenic beauty and exceptional vineyard experiences. Nestled in the heart of Virginia's wine country, this charming town offers numerous wineries, each boasting its own unique charm and range of wines. The picturesque landscapes of the Shenandoah Valley provide a stunning backdrop for your vineyard adventures, making it a great spot for leisurely tastings and vineyard tours.

For couples looking for an intimate experience, the family-owned Veramar Vineyard is a great choice. With its rolling hills and meticulously maintained vineyards, you can enjoy personalised tastings in a romantic setting. The vineyard often hosts special events and live music, creating a delightful atmosphere for a memorable day together.

Families will appreciate the engaging experiences at nearby Narmada Winery. This family-friendly vineyard offers a range of activities, including grape stomping and guided tours that educate visitors about the wine-making process. There's even a picnic area where you can enjoy a relaxing afternoon with the kids while sipping on some fine Virginia wine.

For a more adventurous outing, consider taking a wine-tasting tour that includes several local vineyards. Many companies offer guided tours that include transportation, allowing you to sample a variety of wines without the worry of driving. This is a fantastic way to explore the region and discover hidden gems along the way.
Does Winchester host any wine festivals or events?
Winchester, Virginia, is a hidden gem for wine enthusiasts, offering a delightful array of wine festivals and events throughout the year. The charming town is surrounded by picturesque vineyards and wineries, making it a prime spot for those looking to indulge in local flavours. The annual Shenandoah Valley Wine and Jazz Festival is a highlight, typically held in the summer, where visitors can savour award-winning wines while enjoying live jazz performances in a beautiful outdoor setting.

For couples seeking a romantic experience, the wine events in Winchester provide a great backdrop. Imagine sipping a glass of local Merlot while strolling hand in hand through the lush vineyards, or enjoying a picnic on the grounds of one of the nearby wineries. Many venues also host intimate wine tastings and vineyard tours, allowing couples to learn more about the winemaking process together.

Families can also enjoy the wine culture in Winchester, as many wineries offer family-friendly events. Some host seasonal festivals with activities for children, such as grape stomping and hayrides, ensuring that everyone has a memorable experience. Plus, the scenic landscape is ideal for a family outing, with ample space for picnics and outdoor activities.
How can I save on a winery hotel in Winchester with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining One Key™, Expedia's free travel rewards programme. As a member, you can unlock instant savings and member perks when you're logged in to your account. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Is it cheaper to book flights and a winery hotel in Winchester as a package deal?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my winery hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel winery hotel in Winchester for you.

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