Winchester, VA Vacation Rentals

Our Favorite Vacation Rentals in Winchester

  • Executive Suites
  • Just Like Heaven Carriage House
  • Brookfield Corp Apartments
  • Merrimans Meadow
  • Quiet but In-Town Getaway
  • Pretty Little Apt by the Train I
  • City Charmer minutes from Old Town
    Excellent2br Home/Apartment
  • Cozy Cottage -Private entrance& Living area
    Excellent2br Cottage

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Winchester Vacation Rentals with Wi-Fi

  • Historic District Charm On Cameron Street
    Excellent3br Home/Apartment
  • ANS Inn & Suites (Efficiency Suites)
  • Serenity Now! Cabin
    Excellent2br Cabin
  • Colonial Getaway Near Old Town Historic Winchester
    Excellent3br Home/Apartment

Winchester Pet-Friendly Vacation Rentals

  • The Lodge Retreat
     4br Home/Apartment
  • The Blue Door steps from Handley Library
  • Yellow Submarine steps from Handley Library
     2br Home/Apartment
  • Beautiful Furnished Apartments

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° 21°
61° 14°
81° 10°
72° 21°
82° 25°
90° 41°
91° 48°
91° 50°
90° 52°
90° 50°
86° 28°
Rainy days

This climate histogram shows you the weather patterns in Winchester. The warmest months in Winchester are July and June, when temperatures reach 91 ˚F. The coolest month is December, when temperatures drop to 0 ˚F. The wettest month in Winchester is July with 10.46 inches of rain, while the driest month is October with 1.82 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

Vacation Rentals in Winchester

At we have rentals from all of the leading providers - Airbnb, Priceline, Agoda and others. Winchester has 420 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. A trip to Winchester can be affordable - our cheapest price accommodation is available at $20 per night. In general, a place to stay in Winchester will cost you $88 per night.

If you need to stay connected during your vacation, then you can choose from over 115 accommodations in Winchester that have WiFi. 27 of our accommodations include a breakfast in the price. You can maintain your workout routine by staying at one of 21 accommodations that provide gym facilities. Driving to Winchester? Then choose one of the 120 places to stay that comes with a parking spot included. We have 16 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 29 pet-friendly places to stay in Winchester, so if you're traveling with your cat or dog you won't have any problems.

We combine a wide variety of Winchester accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 105 places to stay from Airbnb, 19 accommodations from Priceline and 9 places to stay from Agoda.

200 of the accommodations in Winchester have been reviewed and rated. 74% are rated excellent or good. 80 accommodations allow instant booking.

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