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Our top choices for Winchester ski hotels

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very good, (1,001 reviews)
"Nice room and good location for an overnight stay."
United States
Edward
The price is CA $113
CA $126 total
includes taxes & fees
Mar 31 - Apr 1
Ramada by Wyndham Strasburg/Shenandoah Valley

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,000 reviews)
"Location of hotel is great for walking to restaurants and shops. "
United States
Paul
The price is CA $170
CA $192 total
includes taxes & fees
Apr 12 - Apr 13
The George Washington Hotel, A Wyndham Grand Hotel

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean, staff was very polite and efficient."
United States
Marc
The price is CA $139
CA $154 total
includes taxes & fees
Apr 12 - Apr 13
DoubleTree by Hilton Front Royal Blue Ridge Shadows

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (494 reviews)
"Great place to rest. Clean and family/pet friendly. "
United States
Noe
The price is CA $157
CA $170 total
includes taxes & fees
Mar 29 - Mar 30
TownePlace Suites by Marriott Winchester

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
Front Royal
6.8 out of 10, (508 reviews)
"Nice room. Very clean. No continental breakfast. Had to climb 9 stairs to get into lobby. Night attendant was very nice."
Canada
Debbie
The price is CA $75
CA $83 total
includes taxes & fees
Apr 9 - Apr 10
Motel 6 Front Royal, VA

Days Inn by Wyndham Luray Shenandoah

Days Inn by Wyndham Luray Shenandoah
2.0 star property
Luray
6.6 out of 10, (1,000 reviews)
"The room was clean, the service was fast, and the grounds were well kept."
United States
Adam
The price is CA $90
CA $104 total
includes taxes & fees
Mar 30 - Mar 31
Days Inn by Wyndham Luray Shenandoah

Motel 6 Mount Jackson, VA - Shenandoah

Motel 6 Mount Jackson, VA - Shenandoah
2.0 star property
Mount Jackson
7.8 out of 10, Good, (1,000 reviews)
"the mountains are beautiful and the town is cute "
United States
Alessandra
The price is CA $85
CA $93 total
includes taxes & fees
Mar 29 - Mar 30
Motel 6 Mount Jackson, VA - Shenandoah

Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA
2.5 star property
Woodstock
8.8 out of 10, Excellent, (1,002 reviews)
"Check in was easy, convenient location to highway, indoor pool major bonus - even though it was too cold to swim in. We stayed twice within a week. Would recommend."
United States
Patricia
The price is CA $136
CA $152 total
includes taxes & fees
Apr 5 - Apr 6
Hampton Inn & Suites Woodstock, VA

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America
3.0 star property
Luray
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice hotel with lots of history "
United States
Patrick
The price is CA $115
CA $142 total
includes taxes & fees
Apr 12 - Apr 13
Mimslyn Inn Historic Hotels Of America

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (39 reviews)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
The price is CA $187
CA $210 total
includes taxes & fees
Mar 30 - Mar 31
Roadhaven1830
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.

Choose what matters most at ski hotels in Winchester

Top Winchester Hotel Reviews

Frequently asked questions

What are the top-rated ski hotels in Winchester?
Some of the top-rated ski hotels in Winchester include The George Washington Hotel, TownePlace Suites by Marriott Winchester, and Hampton Inn Winchester N/Conference Center, VA.

The 3.5-star The George Washington Hotel, A Wyndham Grand Hotel, boasts a superb 9.4 rating and offers convenient access to both downhill and cross-country skiing opportunities. Guests also appreciate the comfortable and clean rooms.

With a 9.2 rating, the Hampton Inn Winchester N/Conference Center, VA provides a complimentary buffet breakfast to fuel your ski days and is situated near local ski areas. Many guests praise the friendly and helpful staff.

The 3-star TownePlace Suites by Marriott Winchester, rated 8.8, is located close to downhill skiing and offers a free continental breakfast. Additionally, it features both an indoor and outdoor pool, which can be a welcome amenity after a day on the slopes.
How much does a ski hotel in Winchester cost?
Prices for ski hotels in Winchester can vary, but you can find a great deal from CA $83 on Expedia. All sorts of factors affect price, such as the hotel's proximity to the slopes and the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.
What ski hotels in Winchester are best for families?
For families visiting Winchester, hotel choices include The George Washington Hotel, A Wyndham Grand Hotel, Hampton Inn Winchester N/Conference Center, VA, and TownePlace Suites by Marriott Winchester.

The 3.5-star George Washington Hotel, a Wyndham Grand Hotel, rated 9.4, is a great option for families with its comfortable and clean rooms, and it provides free cots upon request. The hotel also offers free WiFi and is conveniently located near both cross-country and downhill ski areas.

The Hampton Inn Winchester N/Conference Center, VA, with a 9.2 rating, provides families with a complimentary buffet breakfast each morning, ensuring a good start to a day on the slopes. The hotel also has free WiFi and is situated close to ski locations.

The 3-star TownePlace Suites by Marriott Winchester, with an 8.8 rating, offers families the convenience of free continental breakfast and self-parking. Guests can also enjoy the outdoor pool, which can be a fun activity after a day of skiing, and it's near downhill ski options.
Is Winchester good for skiing?
Winchester isn't directly a skiing destination, but it serves as a convenient base for accessing several ski resorts in the surrounding region.

For those looking for a winter sports experience, Winchester is a practical choice because it's within a reasonable driving distance of multiple resorts. You'll find resorts offering downhill skiing, snowboarding, and sometimes tubing, typically within a 1 to 2-hour drive. This makes it an ideal spot for couples or families who want to combine a historical trip to Winchester with a day or two on the slopes.

Families, in particular, will appreciate Winchester as a base. After a day of skiing, you can return to a wider range of dining and accommodation options than you might find directly at the resorts, many of which are geared towards a more relaxed evening.
Which area of Winchester is best to stay in for skiing?
For skiing near Winchester, the best area to stay is along the US-50 corridor, specifically in the eastern part of Winchester, or in the nearby town of Front Royal.

Staying along US-50 in eastern Winchester offers convenient access to the main routes leading to the ski resorts. This area has a good selection of hotels and amenities, making it a practical base for skiers. You'll find a variety of dining options and shops for any last-minute needs before heading to the slopes.

Front Royal, a short drive south-east of Winchester, is another excellent option. It's closer to some of the prominent ski resorts and provides a more direct route to the mountains. This town offers a selection of accommodation, often at a good value, and maintains a pleasant, small-town atmosphere.
Is it cheaper to book flights and a ski hotel in Winchester as a package?
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.
What dining options are typically available in Winchester ski accommodations?
The best area to stay in Winchester is the historic Old Town, particularly around the Loudoun Street Walking Mall.

This area is the heart of Winchester, known for its pedestrian-friendly Loudoun Street Walking Mall, which is lined with independent shops, restaurants, and historic buildings dating back to the 18th century. You'll find many of the city's main attractions here, including the Handley Regional Library and the Old Town Hall. It's very walkable and provides a central base for exploring.

Couples will find Old Town particularly appealing for its romantic setting and diverse dining options. Many of the city's best restaurants, from casual bistros to fine dining establishments, are located along the Walking Mall or just off it, making evening strolls and dinner plans effortless. The area also offers a selection of independent boutiques and art galleries for leisurely browsing.

For travellers interested in history and culture, Old Town is an excellent choice. It provides easy access to several museums and historic homes, such as the George Washington's Office Museum and the Stonewall Jackson's Headquarters Museum, all within a short walk.
What activities should we do in Winchester besides skiing?
The best area to stay in Winchester for exploring activities beyond skiing is the historic Old Town, particularly around the Loudoun Street Walking Mall.

This area is the heart of Winchester, known for its pedestrian-friendly Loudoun Street, which is lined with independently owned shops, restaurants, and centuries-old architecture. You'll find landmarks like the Handley Regional Library and the Old Court House here, all within a compact and easily navigable space.

Couples often find Old Town ideal for a relaxing getaway. You can spend your days browsing the boutiques, enjoying meals at various eateries, and visiting historic sites such as George Washington's Office Museum or the Museum of the Shenandoah Valley. Evenings can be spent enjoying a show at the Bright Box Theater or simply strolling hand-in-hand along the lit-up mall.

For those interested in history, the Old Town offers easy access to multiple Civil War battlefields and museums, including the Shenandoah Valley Civil War Museum and the Third Winchester Battlefield.
How can I save on a ski hotel in Winchester with Expedia?
Members always get our best prices. Find our best Winchester ski hotel deals by joining Expedia's free travel rewards program—One Key™. As a member, you can unlock instant savings and member perks when you're logged in. Another tip is to book your ski hotel in advance as availability and prices are usually better. If you are feeling spontaneous, there are last-minute offers to explore too.
Can I cancel my ski hotel reservation on Expedia?
If your plans change, it's easy to cancel your hotel with free cancellation on Expedia. Just use the "Fully refundable property" filter during your search to find the right ski hotel in Winchester. Before confirming your booking, review the property's cancellation policy for complete peace of mind.

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