Winchester, VA Vacation Rentals

Check prices for these upcoming dates

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

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
91° 52°
2
93° 45°
1
91° 32°
4
66° 19°
1
61° 16°
3
61°
3
66°
4
73° 14°
3
81° 28°
4
88° 37°
6
91° 41°
2
97° 54°
4
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Rainy days

This climate histogram shows you the weather patterns in Winchester. The hottest month in Winchester is June, when temperatures peak at 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

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — 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
  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy

Vacation Rentals in Winchester

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, Priceline, Agoda and others. We have 358 vacation rentals, hotels and other accommodation types in Winchester ranging from budget options to extravagant places to stay. For those wanting to keep costs down, the lowest priced place to stay in Winchester comes in at $20 per night. In general, an accommodation in Winchester will cost you $87 per night.

If you want an internet connection during your time in Winchester, then you can choose from over 131 accommodations that have WiFi internet. 13 places to stay include a morning meal. You can keep up with your workout routine by staying at one of 22 accommodations that provide gym facilities. If you are driving to Winchester, you'll want to pick from 133 places to stay that provide parking. We track 16 accommodations that have a pool or jacuzzi.

If you're traveling with your best friend, then be sure to select one of the 36 pet-friendly accommodations available.

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 116 places to stay from Airbnb, 22 accommodations from Priceline and 9 places to stay from Agoda.

196 of our accommodations in Winchester have been reviewed and rated. 72% are rated excellent or good. 87 accommodations allow instant booking.

Destinations near Winchester

  • Williamsburg3,498 Properties
  • Virginia Beach2,776 Properties
  • Norfolk1,908 Properties
  • Richmond1,421 Properties
  • Charlottesville1,169 Properties
  • Arlington1,078 Properties
  • Luray759 Properties
  • Chincoteague724 Properties
  • Newport News724 Properties
  • Fredericksburg666 Properties
  • Blacksburg634 Properties
  • Roanoke593 Properties
  • Reston491 Properties
  • Lexington486 Properties
  • Harrisonburg473 Properties
  • Herndon468 Properties
  • McLean465 Properties
  • Alexandria449 Properties
  • Moneta447 Properties
  • Massanutten435 Properties
  • Glen Allen424 Properties
  • Vienna371 Properties
  • Staunton357 Properties
  • Portsmouth354 Properties
  • Cape Charles354 Properties
  • Huddleston353 Properties
  • Chesapeake352 Properties
  • Chantilly331 Properties
  • Abingdon326 Properties
  • Woodbridge304 Properties
  • Sterling302 Properties
  • Manassas296 Properties
  • Fairfax292 Properties
  • Springfield265 Properties
  • Hampton263 Properties
  • Stafford257 Properties
  • Petersburg254 Properties
  • Front Royal228 Properties
  • Ashburn210 Properties
  • Colonial Beach189 Properties
  • Falls Church180 Properties
  • Fancy Gap173 Properties
  • Suffolk167 Properties
  • Waynesboro150 Properties
  • Nellysford124 Properties
  • Floyd115 Properties
  • Leesburg108 Properties
  • Damascus106 Properties
  • Galax103 Properties
  • Salem98 Properties
  • Lynchburg89 Properties
  • Woodstock75 Properties
  • Wytheville74 Properties
  • Chester67 Properties
  • Lovettsville65 Properties
  • Ashland60 Properties
  • McGaheysville53 Properties
  • Reedville52 Properties
  • Deltaville33 Properties
  • Hillsville30 Properties
  • Barboursville29 Properties