Woodstock holiday rentals

We found 1,274 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Woodstock that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Woodstock

Showing deals for:16 Oct - 23 Oct

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Why visit Woodstock

  • Outdoor Adventures: Woodstock offers a variety of outdoor activities, including hiking and exploring local national and state parks, as well as intriguing caves.
  • Scenic Beauty: Nestled in the picturesque Shenandoah Valley, the city boasts stunning landscapes that provide a perfect backdrop for relaxation and exploration.
  • Family-Friendly Experiences: The city is ideal for family getaways, with cosy accommodations and ample opportunities for family fun.
  • Historical Charm: Visitors can enjoy the rich history of Woodstock, with various historical landmarks to explore.
  • Friendly Locals: The welcoming atmosphere and friendly locals enhance the overall experience, making visitors feel at home.

Popular types of accommodation in Woodstock

Woodstock, Virginia, is a charming city offering a delightful selection of holiday rentals, including cosy cabins, private homes, and quaint cottages. Nestled in the picturesque Shenandoah Valley, visitors can explore stunning natural landscapes, historic landmarks, and outdoor activities. Whether you're seeking a peaceful retreat or an adventure-filled getaway, Woodstock provides affordable accommodation options that promise comfort and convenience for every traveller.

  • Cabins: Experience a cosy retreat in a traditional woodland cabin, the top choice among visitors in Woodstock.
  • Private Holiday Homes: Enjoy complete privacy in a standalone holiday home, the second most sought-after option.
  • Cottages: Relish a quaint, charming cottage stay, ranked third in popularity.
  • Condos: Opt for a modern and convenient condo, fourth in the booking list.
  • Apartments: Choose a comfortable apartment, preferred by visitors as the fifth option.**

Top attractions in Woodstock

Woodstock, Virginia offers an inviting blend of outdoor adventures and scenic beauty. Visitors can explore local national and state parks, intriguing caves, and picturesque parks, making it a perfect destination for cultural, outdoor, and family experiences. As the day turns to evening, enjoy nearby attractions and lively fun evenings, capturing the essence of this charming city.

  • W.O. Riley Park: Enjoy eco-friendly outdoor family fun in Woodstock at this park, where nature and community blend seamlessly.
  • Shenandoah County Fairgrounds: Experience the charm of traditional county fairs in Woodstock, offering a welcoming atmosphere and outdoor family activities.
  • Woodstock Tower Observation Site: Embrace adventure and romance with breathtaking views from this lookout in Woodstock, perfect for an inspiring outdoor experience.

Things to do recommended for couples

Discover rustic charm in Woodstock, Virginia, perfect for couples. Enjoy a leisurely walk through scenic trails, indulge in local cuisine, and unwind in cosy cafes, experiencing the warmth of a genuine local welcome.

Things to do recommended for families

Families visiting Woodstock, Virginia, can explore the beautiful Shenandoah National Park, enjoy a scenic hike, and visit the Virginia Museum of the Civil War for engaging exhibits. Don't miss the chance to pick fresh apples at local orchards during the harvest season for a delightful experience.

Things to do recommended for groups

Explore the stunning landscapes of the Shenandoah Valley with a group hike along the scenic trails of George Washington National Forest. Alternatively, enjoy a wine tasting tour at nearby vineyards, where you can savour local vintages and indulge in delightful picnic experiences.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Woodstock

If you're travelling with a group, family, pets, or seeking extended stays, be sure to apply the appropriate filters to meet your priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Stayz.
  • Traveling to Woodstock with young kids: Travel with young children can present its challenges. It is important to prioritise their comfort and safety, along with ensuring access to age-appropriate facilities, such as a private swimming pool. Additionally, it is wise to consider your nearness to attractions that cater to families.
  • Taking your pets with you to Woodstock: For some, a family holiday is not complete without the presence of their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels right at home.
  • Planning for a long term stay visiting Woodstock: If you're seeking holiday lets with special offers for month-long stays or more, you've come to the right place. With the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also consider refining your search by including features such as parking, a well-equipped kitchen, or a private pool.

Where to stay near Woodstock

Woodstock, Virginia offers a delightful retreat with a blend of historical charm and natural scenery. Enjoy a relaxing stay in cosy, family-friendly accommodations, perfect for a rooty hill experience and a family getaway. The city embraces outdoor adventures and scenic excursions, ensuring a wonderful stay with friendly locals and secluded spots that capture the essence of a rural, historical retreat.

  • Luray: Luray is a vibrant city situated 24km from Woodstock, inviting travellers to a world of outdoor adventures and scenic beauty. This locale is perfect for those seeking exhilarating experiences in nature, with ample opportunities for skiing at nearby ski fields and enjoying the expansive recreational areas. With national state parks, national parks, and local parks in close proximity, Luray offers a compelling blend of adventure and tranquillity amid its breathtaking landscapes.
  • Rileyville: Rileyville is a dynamic city, located 16km from Woodstock, that promises a rich outdoor and adventure experience. Its surroundings boast a range of activities from skiing on nearby slopes to exploring recreational areas. The scenic vistas of national state parks, national parks, and local parks provide a picturesque backdrop for leisurely walks and invigorating outdoor pursuits, making Rileyville a delightful destination for nature enthusiasts.
  • Willow Grove: Willow Grove is a charming village merely 5km from Woodstock, ideal for those desiring a blend of outdoor exploration and urban family experiences. The area is known for its well-maintained golf courses and educational venues, while local urban parks and historic sites offer a cultural touch to the visit. Its close proximity ensures travellers can easily enjoy the lively city-themed attractions alongside the serenity of rural life.

Best time to go to Woodstock

If you're planning a trip to Woodstock, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowAverage
February34.7°F (1.5°C)Light RainMostly SunnyAverageAverage
March42.3°F (5.7°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnyAverageSlightly Low
May62.1°F (16.7°C)Light RainMostly SunnyAverageAverage
June70.2°F (21.2°C)Light RainMostly SunnySlightly HighAverage
July75.0°F (23.9°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
September66.0°F (18.9°C)Light RainMostly SunnyAverageSlightly Low
October55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
November43.0°F (6.1°C)Light RainMostly SunnySlightly LowSlightly High
December36.5°F (2.5°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Stayz is simple

Looking to make your next holiday more affordable? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay frequently results in substantial savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's Trip Board provides an excellent platform for you to plan new journeys, refine your existing arrangements, or manage your bookings effectively. Your saved or reserved properties are conveniently organised into categories such as Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Why people love visiting friendly Woodstock

Learn about the unique charm of Woodstock with a stay in a holiday home rental. Travellers to this welcoming city praise the restaurants, shopping and hiking. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Woodstock

Are you searching for attractions to see during your stay? Venture out of your holiday home and experience everything that makes Woodstock a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah Vineyards (3.8 mi / 6 km)
  • Bryce Ski Resort (14.8 mi / 23.8 km)
  • Yogi Bear's Jellystone Park (15.7 mi / 25.3 km)
  • Wisteria Farm and Vineyard (21.3 mi / 34.3 km)
  • Cave Ridge Vineyard (9.8 mi / 15.8 km)
  • Mt Jackson Thrift & Gift (12 mi / 19.2 km)

Exploring the natural landscape of Woodstock

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Woodstock is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Luray Caverns (15.1 mi / 24.3 km)
  • Shenandoah National Park (25.4 mi / 40.9 km)
  • Massanutten Storybook Trail (10.6 mi / 17.1 km)
  • Shenandoah Caverns (14.5 mi / 23.3 km)
  • Skyline Caverns (15.6 mi / 25.1 km)
  • Front Royal Entrance Shenandoah National Park (16.9 mi / 27.2 km)

How to get to and around Woodstock

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 47.7 mi (76.8 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Woodstock?
Based on our research, houses are the most sought-after holiday property type in Woodstock. But having said that, everyone's idea of an epic trip can differ. Stayz has holiday homes in a variety of shapes and sizes, so you're sure to discover the best fit for your needs.
How much does it cost to rent a holiday home in Woodstock?
Length of stay, property type and time of year are some factors that can influence the price of a holiday home. Simply click on your dates of travel to find your perfect escape. From comfy cabins to plush villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Woodstock?
Prices for beach houses in Woodstock can vary depending on the type and size of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and the number of guests to view holiday home options and prices. From there you can use the filters to narrow down your search by ratings, amenities and more.
Are there pet-friendly holiday homes in Woodstock?
Pack a suitcase and a bone for your puppy dog because Woodstock has two stays that open their doors to pets. Let your happy hound have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and travel dates, then check the "Pets allowed" filter box.
What are popular home amenities in Woodstock?
The most popular home amenities people search for in Woodstock are a barbecue grill, a fireplace and a firepit. Whether you're travelling with friends, family or even pets, Stayz holiday properties have the best amenities for beginning new traditions with the people that matter most.
Are there holiday homes in Woodstock that welcome kids?
Gather your entire family for a fun-filled adventure in Woodstock at one of our two family-friendly properties. Many of these stays come with amenities that are perfect for trips with youngsters, including full kitchens, living rooms and private pools. Simply click on the "Properties good for families" filter box and select your favourite.
What are the top attractions for families in Woodstock?
Keeping the kids happy during your stay in Woodstock is simple with these cool family-friendly attractions:

  • Edinburg Mill Museum
  • Secret Passage Ranch
  • Seven Bends State Park

Are there holiday homes with WiFi in Woodstock?
Woodstock has two holiday homes with WiFi, so you can stay connected while you're travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movie blockbusters to checking emails, these Stayz homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Woodstock?
You'll have a choice of two Stayz holiday homes with air conditioning in Woodstock offering that cooling breeze and extra comfort level. Enter your dates of travel and then make use of our filters to help you find stays with air conditioning.
How old do you have to be to rent a holiday home in Woodstock?
We recommend checking with the Woodstock holiday property you're looking at on Stayz as age restrictions vary. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Woodstock for?
The amount of time you can book a Woodstock holiday home for is down to each property. Just tap in your dates of travel to browse available options that offer extended stays. They have all the things you need to make your extended holiday more comfortable and enjoyable, such as kitchens and backyards. Some holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.