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

Best Resorts in Winchester

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Winchester resorts

A hotel lobby with a fireplace, two armchairs, a chandelier, and a display of toiletries.

1. Lansdowne Resort and Spa

Lansdowne Resort and Spa
4.0 star property
Leesburg
9.0 out of 10, Wonderful, (1,000 reviews)
"Great ambiance with amazing views. It was a perfect and close get away."
United States
Gabriel
$215 nightly
The price is $245
Nov 22 - Nov 23
Total with taxes and fees
Lansdowne Resort and Spa
A large, multi-story building with a symmetrical facade, multiple chimneys, and a central entrance with columns.

2. Salamander Middleburg

Salamander Middleburg
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (427 reviews)
"Great place, and nice staff"
United States
Mohamed
$685 nightly
The price is $781
Nov 1 - Nov 2
Total with taxes and fees
Salamander Middleburg
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

Skyland

Skyland

8/10 Good
"The shower had rather low water pressure and it took a couple tries to get the space heater in the bathroom to work. Other than that, clean comfortable room."
Robert 3-night trip
Posted 8 hours ago
Skyland

Find out more about Winchester

Winchester Resorts information

Number of reviews
1,000
Accommodation
4 Resorts
Lowest Price
$245
Highest Price
$781

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: Salamander Resort And Spa - Luxury resort. 26.9 mi (43.3 km) from Winchester. Features 2 restaurants, a full-service spa, and a seasonal outdoor pool. Lansdowne Resort and Spa - Family-friendly resort. 37.6 mi (60.5 km) from Winchester. Has a golf course, a seasonal outdoor pool, and 3 outdoor tennis courts. 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 Bright Box Theater 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.

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