Winchester, VA Vacation Rentals

Our Favorite Vacation Rentals in Winchester

  • Executive Suites
     Home/Apartment
    Booking.com
    From
    $82
  • Just Like Heaven Carriage House
    NiceCottage
    HolidayLettings
    From
    $215
  • Brookfield Corp Apartments
     Home/Apartment
    Booking.com
    From
    $94
  • Merrimans Meadow
    ExcellentHome/Apartment
    Airbnb
    From
    $136
  • Cabin in the woods
    Good4br Home/Apartment
    Airbnb
    From
    $636
  • Quiet but In-Town Getaway
    ExcellentHome/Apartment
    Airbnb
    From
    $85
  • Pink door cottage.Private entrance & living area.
    ExcellentCottage
    Airbnb
    From
    $96
  • ANS Inn & Suites (Efficiency Suites)
    ExcellentHome/Apartment
    Airbnb
    From
    $68

Check prices for these upcoming dates

Winchester Vacation Rentals with Wi-Fi

  • Lovely Lofts
     Home/Apartment
    Airbnb
    From
    $79
  • Quiet Carriage House Apartment w/Mountain Views
     Home/Apartment
    Airbnb
    From
    $79
  • Serenity Now! Cabin
    Excellent2br Cabin
    Airbnb
    From
    $325
  • The Murphy Van!
     Home/Apartment
    Airbnb
    From
    $67

Winchester Pet-Friendly Vacation Rentals

  • The Lodge Retreat
     4br Home/Apartment
    Airbnb
    From
    $1,187
  • Lux Downtown Home
    Excellent3br Home/Apartment
    Airbnb
    From
    $124
  • Executive Suites
     Home/Apartment
    Airbnb
    From
    $79
  • Beautiful Furnished Apartments
     Home/Apartment
    Airbnb
    From
    $90

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
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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
90 º50
7
86 º28
2
73 º21
6
61 º14
4
68 º0
2
81 º10
3
72 º21
2
82 º25
3
90 º41
9
91 º48
10
91 º50
7
90 º52
4
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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 love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — 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 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

Vacation Rentals in Winchester

At AllTheRooms.com we have rentals from all of the best providers - Airbnb, Priceline, Agoda and others. AllTheRooms has 400 rentals, hotels and other great places to stay while you enjoy Winchester, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Winchester is available at $21 per night. The average price of a vacation rental is generally $91 per night.

If you want to stay connected during your vacation, then you can choose from over 108 accommodations in Winchester that have WiFi. 27 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're planning on arriving in Winchester by car, be sure to choose from 116 accommodations that provide parking. 16 vacation rentals have a a pool or jacuzzi

AllTheRooms has 28 pet-friendly places to stay in Winchester, so if you're traveling with your pet you won't have any problems.

In Winchester AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 3 providers, including 96 places to stay from Airbnb, 9 accommodations from Priceline and 9 places to stay from Agoda.

207 of our accommodations in Winchester have been reviewed and rated. 67% are rated excellent or good. 79 places to stay in are instantly bookable.

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