Winchester, VA Vacation Rentals

Our Favorite Vacation Rentals in Winchester

  • Executive Suites
  • Just Like Heaven Carriage House
  • Quiet but In-Town Getaway
  • Historic Seymour House in Old Town
  • Cozy Cottage -Private entrance& Living area
    Excellent2br Cottage
  • Historic District Charm On Cameron Street
    Excellent3br Home/Apartment
  • Quiet Carriage House Apartment w/Mountain Views
  • Minutes from Downtown, Great Food & Entertainment!
    Excellent3br Home/Apartment

Check prices for these upcoming dates

Winchester Vacation Rentals with Wi-Fi

  • Serenity Now! Cabin
    Excellent2br Cabin
  • Beautiful Furnished Apartments
  • Majestic Mountain Cabin
    Excellent2br Home/Apartment
  • Emma's Stone Cottage
    Excellent2br Home/Apartment

Winchester Pet-Friendly Vacation Rentals

  • Cozy cottage on organic solar powered farm
  • The Lodge Retreat
     4br Home/Apartment
  • Yellow Submarine steps from Handley Library
    Excellent2br Home/Apartment
  • Winchester Executive Suites

Winchester Travel Guide

In the Shenandoah Valley of northern Virginia lies Winchester. It's a small city that played an important part in the Civil War but nowadays it serves as a small hub for tourism as it's home to leafy green parks, springs, forests, alongside history and museums.

Things to Do in Winchester

To experience the beauty of Winchester, visitors flock to Jim Barnett Park to explore its various trails and enjoy its year-round indoor and outdoor pools. Other great parks in the area include the Frederick Douglass Park and Weaver Park, both of which are ideal for playing soccer and field sports.

Shawnee Springs Preserve, the site of an old Civil War hospital, is the perfect place to admire some of Winchester’s most scenic wetlands, lush forests, and trickling springs.

Meanwhile, history buffs will be amazed by the various historical sites and museums in Winchester, including Stonewall Jackson’s Headquarters, Handley Regional Library, Virginia Museum of Veiled History, Shenandoah Valley Civil War Museum, and the Shenandoah Valley Discovery Museum.

Guests looking to soak in views of the epic Blue Ridge mountain range can make their way to Marker-Miller Orchards to sample tasty cider, donuts, and slushies, and marvel over the countryside views.

Best Places to Stay in Winchester

As for vacation homes, Winchester has a great selection. From log cabins to modern three-story houses, the city has the perfect rental for everyone. Many of the rentals are not only stylish but friendly and spacious, as well, with great views of the surrounding mountains.

Best Time to Visit Winchester

The best time to visit Winchester is from mid-June to July when the sun is shining and the warm weather is at its finest.

Best Events in Winchester

A few of the most exciting things in Winchester are the city's annual events. For example, the St. Paddy's Celtic Fest celebrates everything Celtic, featuring Celtic-themed games, balloon animals, face painting, dancing and music, food vendors, a photo booth, bagpipers, movies, and a petting zoo. Other fun events include the Rockin’ Independence Day Eve, Oktoberfest, and Holly Jolly Celebration.

Things to Do for Families in Winchester

Animal-loving families can spend the day amongst horses at the Rocking S Ranch. The ranch offers guided horseback trail rides with friendly guides that can take riders through streams, forests, fields, and wetlands. They can also feed the animals at Wilson’s Wild Animal Park. Shopping is another great activity, with Winchester offering Apple Blossom Mall and Creekside Station, alongside a dozen other unique shops and local boutiques.

Price and Availability in Winchester

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The cheapest day to stay at a vacation rental in Winchester tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Winchester tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Winchester is in December, while the cheapest month is in March. The most popular time to book a vacation rental in Winchester is in the high season in July. Winchester has its low season in March, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Winchester

Rainy days
73° 14°
81° 28°
88° 37°
91° 41°
97° 54°
91° 52°
93° 45°
91° 32°
66° 19°
61° 16°
Rainy days

This climate histogram shows you the weather patterns in Winchester. The warmest months in Winchester are June and April, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to 1 ˚F. The wettest month in Winchester is August with 6.12 inches of rain, while the driest month is February with 0.55 inches of rain.

What Expert Travelers Think

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    Samantha Wragg
    Samantha WraggCoco Travels
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    Max Hobbs
    Max HobbsLTL Mandarin School
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

Vacation Rentals in Winchester

Browse rentals from all your favorite providers including Airbnb, Priceline, Agoda and many more at AllTheRooms has 353 rentals, hotels and other great places to stay during your time in Winchester, with everything from inexpensive hostels and homestays to extravagant Airbnbs and hotels. For those trying to save money, the cheapest place to stay in Winchester is only $20 a night. An average accommodation in Winchester costs on average $88 per night.

Those looking to get some work done during their trip to Winchester can choose from 126 places to stay that provide WiFi. 12 places to stay include a breakfast. Fitness fanatics can get a workout in during their stay by choosing from 22 accommodations that have gyms. Driving to Winchester? Then choose one of the 128 places to stay that comes with a parking spot included. 16 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then make sure to choose one of the 36 pet-friendly accommodations available.

In Winchester AllTheRooms currently compares hotels, vacation rentals, hostels from more than 3 providers, including 111 places to stay from Airbnb, 9 accommodations from Priceline and 9 places to stay from Agoda.

178 of our accommodations in Winchester have been reviewed and rated. 74% are rated excellent or good. 88 places to stay in are instantly bookable.

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