Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Tonight Feb 26 - Feb 27
This weekend Feb 28 - Mar 1
Next weekend Mar 6 - Mar 8

Best Luxury Hotels in Winchester

$55
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.0 out of 5.0 160 Front Royal Pike, Winchester, VA
3.6/5
(43 Reviews)
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
$53
Motel 6 Winchester, VA

Motel 6 Winchester, VA

2.0 out of 5.0 2951 Valley Avenue, Winchester, VA
3.5/5
(10 Reviews)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Get Rates
The Ashby Inn & Restaurant

The Ashby Inn & Restaurant

3.5 out of 5.0 692 Federal St, Paris, VA
3/5
(1 Reviews)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

5 Star Hotels in Winchester

$395
The Inn At Little Washington

The Inn At Little Washington

5.0 out of 5.0 Middle And Main Streets, Washington, VA
5/5
(1 Reviews)
Situated in a rural location, this luxury hotel is steps from R.H. Ballard Shop & Gallery, The Theatre at Washington, and The First Washington of All Monument. Little Washington Winery is 2.5 mi (4 km) away.
$450
Salamander Resort And Spa

Salamander Resort And Spa

5.0 out of 5.0 500 North Pendleton Street, Middleburg, VA
4.5/5
(2 Reviews)
This family-friendly Middleburg resort is located in the historical district, within 3 mi (5 km) of National Sporting Library & Museum and Greenhill Winery & Vineyards. Aldie Mill Historic Park and Chrysalis Vineyards are also within 6 mi (10 km).
Celebration Retreat

Celebration Retreat

5.0 out of 5.0 440 Scenic Overlook Dr, Front Royal, VA
Situated in Front Royal, this luxury vacation home is within 6 mi (10 km) of Tuckers Lane Trailhead, Front Royal Visitor's Center, and Blue Ridge Arts Council and Gallery. Warren Rifles Confederate Museum and Belle Boyd Cottage are also within 6 mi (10 km).

4 Star Hotels in Winchester

$249
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4.0 out of 5.0 2 E Washington St, Middleburg, VA
5/5
(1 Reviews)
Located in the heart of Middleburg, this inn is 1.7 mi (2.8 km) from Greenhill Winery & Vineyards and within 6 mi (10 km) of Chrysalis Vineyards and Aldie Mill Historic Park. Stone Tower Winery and Winery at La Grange are also within 16 mi (25 km).
$280
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4.0 out of 5.0 44050 Woodridge Pkwy, Leesburg, VA
4/5
(10 Reviews)
Located near the airport, this family-friendly resort is within 9 mi (15 km) of Village at Leesburg, Lost Rhino Brewing Company, and Old Ox Brewery. Morven Park and Stone Tower Winery are also within 12 mi (20 km).
$179
L'Auberge Provencale

L'Auberge Provencale

4.0 out of 5.0 13630 Lord Fairfax Hwy, White Post, VA
Situated in White Post, this hotel is 2.4 mi (3.9 km) from State Arboretum of Virginia and 3.1 mi (4.9 km) from Dinosaur Land. Wilson's Wild Animal Park and Burwell-Morgan Mill are also within 6 mi (10 km).

Travelers Like You Recently Booked These Winchester Hotels

Map

Winchester Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Winchester luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Winchester to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in Winchester will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Winchester, and plan your next opulent escape.


Recent Winchester Hotel Reviews By Fellow Wanderers

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.