A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Best Resorts in Winchester

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Winchester resorts

Indoor pool, seasonal outdoor pool

1. Lansdowne Resort and Spa

Lansdowne Resort and Spa
4.0 star property
Leesburg
9.0 out of 10, Wonderful, (1,000 reviews)
"Everything was great !"
United States
Dwayne
$255 nightly
The price is $291
Aug 30 - Aug 31
Total with taxes and fees
Lansdowne Resort and Spa
Exterior

2. Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (414 reviews)
"Very refreshing breakfast experience and the staff was great."
United States
Wayne
$737 nightly
The price is $840
Sep 7 - Sep 8
Total with taxes and fees
Salamander Resort And Spa
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Always a great stay! Friendly staff, convenient to the university. Clean and quiet! Thank you again"
Paul 1-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Resorts information

Number of reviews
1,000
Accommodation
4 Resorts
Lowest Price
$291
Highest Price
$840

Frequently asked questions

What is Winchester like for a resort vacation?
Longing for a relaxing escape? Indulge in all the comforts and luxuries of a resort, where you can find everything you want for your vacation from tasty dining options to entertainment and shopping. Browse the resorts in the area and discover the right one for you, whether you picture yourself sipping drinks by a sprawling pool or heading to the spa for a deep-tissue massage.
What's the best resort for my stay in Winchester?
Our highest-rated resorts near Winchester: Lansdowne Resort and Spa - Family-friendly resort. 37.6 mi (60.5 km) from Winchester. Features a golf course, a seasonal outdoor pool, and 3 outdoor tennis courts. Salamander Resort And Spa - Luxury resort. 26.9 mi (43.3 km) from Winchester. Has 2 restaurants, a full-service spa, and a seasonal outdoor pool. GolfView Chalet at the Woods Resort, Central Air and Heat - Family-friendly resort. 26.3 mi (42.3 km) from Winchester. Amenities include a hot tub.
What can I do in Winchester?
Travelers come to Winchester to visit its historic sites and other landmarks, and love its popular activities such as shopping. Head to Apple Blossom Mall and Apple Valley Square Shopping Center for some retail therapy, or take the whole family to Shenandoah Valley Discovery Museum and Rocking S Ranch. Additional attractions in the area include Stonewall Jackson's Headquarters and Patsy Cline Historic House.
What's the weather like in Winchester?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What's the best way to get to and around Winchester?
Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) away from the heart of the city. Otherwise, you can search for flights to Washington Dulles Intl. Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia