Woodstock vacation rentals

We found 1,191 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Woodstock that are perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, such as a fireplace and garden. At the end of the day, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Woodstock

Showing deals for:Oct 17 - Oct 24
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Find out more about Woodstock

Why visit Woodstock

  1. Outdoor Adventures: Woodstock is ideal for hiking, exploring local caves, and enjoying the scenic beauty of national and state parks.
  2. Rich History: Discover charming historical houses that showcase the area’s heritage and culture.
  3. Family-Friendly Atmosphere: The town offers a welcoming vibe perfect for family outings and adventures.
  4. Diverse Accommodations: Choose from cozy cabins, modern condos, or spacious homes to suit any budget or preference.
  5. Relaxing Neighborhoods: Explore nearby neighborhoods for a peaceful retreat and local charm.

Popular types of accommodation in Woodstock

Planning a getaway to Woodstock? You're in for a treat! Discover the charm of this beautiful area with a variety of vacation rentals, including cozy cabins, modern condos, and spacious private homes. Whether you're searching for budget-friendly options or looking for apartments in Woodstock, we have you covered. Explore your perfect retreat today and enjoy everything Woodstock has to offer!

  • Cabins: These charming retreats are the top choice for visitors seeking a rustic escape amidst nature's beauty in Woodstock.
  • Condos: Ideal for those who prefer modern comforts, condos offer convenience and amenities for a relaxing stay.
  • Houses: Perfect for families or groups, these homes provide space and a home-like atmosphere during your visit.
  • Apartments: A great option for travelers looking for a cozy and affordable stay in the heart of Woodstock.
  • Cottages: Quaint and picturesque, cottages offer a unique and intimate setting for a memorable getaway.**

Top attractions in Woodstock

Woodstock, Virginia, is a perfect destination for outdoor and adventure enthusiasts, offering stunning scenery and a variety of attractions. Visitors can explore local caves, national and state parks, and nearby mountains, making it ideal for family experiences and cultural outings. Don't miss the chance to view charming houses that reflect the area's rich history. Whether traveling solo or with loved ones, Woodstock promises a memorable getaway filled with nature and adventure.

  1. Luray Caverns: Located 15 miles from Woodstock, Luray Caverns features stunning underground formations, including towering stalactites and expansive chambers. The adventure vibes are heightened by guided tours that take you through this natural wonder, showcasing its beauty and geological significance.
  2. Shenandoah County Fairgrounds: Situated in Woodstock, the Shenandoah County Fairgrounds offers a lively atmosphere for family-friendly events and activities. Enjoy various fairs, concerts, and community gatherings, perfect for creating lasting memories with loved ones.
  3. Woodstock Museum: This local museum celebrates the rich cultural heritage of Woodstock and the surrounding area. Exhibits feature historical artifacts and stories, providing a fascinating glimpse into the past and the community's evolution.

Things to do recommended for couples

For a romantic getaway in Woodstock, explore Shenandoah Vineyards and North Mountain Vineyard for wine tasting in a charming atmosphere. If you're feeling adventurous, head to Bryce Ski Resort for some skiing. These experiences will create unforgettable memories for you and your partner.

Things to do recommended for families

Families visiting Woodstock can explore the enchanting Garden Maze at Luray Caverns, just 15 miles away, or unwind at the Elkwallow Picnic Area, located 14 miles from town, perfect for wellness and relaxation.

Things to do recommended for groups

Explore the scenic Massanutten Storybook Trail for an adventurous hike, visit the charming Natural Art Garden Center for unique finds, and enjoy family fun at Yogi Bear's Jellystone Park campground, all within a short drive from Woodstock.

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

When you're planning a trip—whether with a group, family, pets, or for an extended stay—be sure to prioritize your preferences in the search filters. Here are some useful Vrbo booking tips to help you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind the distance to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Woodstock: For many families, a vacation wouldn't be the same without their beloved pets. If that resonates with you, consider exploring Vrbo listings that welcome furry companions. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Woodstock

Woodstock, Virginia, offers an unforgettable vacation experience filled with outdoor adventures and stunning scenery. Visitors can explore the friendly, family-friendly atmosphere while enjoying relaxing excursions in nearby neighborhoods. From historical sites to secluded nature spots, Woodstock invites travelers to connect with nature and create lasting memories. Whether you're hiking through picturesque landscapes or savoring local charm, there's something for everyone in this beautiful region.

  • Luray: Nestled 15 miles from Woodstock, Luray is a charming city renowned for its stunning outdoor adventures and scenic beauty. Visitors flock to Luray for its breathtaking natural landscapes, including the famous Luray Caverns, where you can explore incredible underground formations. Outdoor enthusiasts can enjoy activities such as hiking in the nearby Shenandoah National Park or skiing at local ski fields during winter. With its combination of natural attractions and recreational areas, Luray is an excellent destination for those seeking both adventure and relaxation.
  • Winchester: Located 28 miles from Woodstock, Winchester offers a delightful blend of history, culture, and outdoor fun. Known for its vibrant downtown area filled with shops and restaurants, visitors can also indulge in recreational activities at nearby parks and lakes. History buffs will appreciate the city’s rich heritage, highlighted by landmarks such as the Old Court House and the George Washington's Office Museum. With opportunities for education and exploration, Winchester is perfect for travelers looking to experience both urban amenities and the beauty of nature.
  • Front Royal: Just 17 miles from Woodstock, Front Royal serves as the gateway to the stunning Shenandoah National Park. This picturesque city attracts adventure seekers with its ample opportunities for hiking, camping, and skiing in the surrounding areas. The town is known for its outdoor recreational areas, making it a popular spot for those wanting to immerse themselves in nature. Front Royal also features charming parks and scenic views, offering a peaceful retreat for visitors looking to unwind while enjoying the great outdoors.

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 LowSlightly Low
February34.7°F (1.5°C)Light RainMostly SunnyAverageSlightly Low
March42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
April52.7°F (11.5°C)Light RainMostly SunnyAverageAverage
May62.1°F (16.7°C)Light RainMostly SunnyAverageAverage
June70.2°F (21.2°C)Light RainMostly SunnySlightly HighSlightly High
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 SunnyAverageAverage
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 Low

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. It truly benefits those who take the lead in planning! By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is a fantastic tool that allows you to plan new trips, pick up right where you left off, or easily view and manage your travel plans. You can find all the properties you've saved and booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Why people love visiting friendly Woodstock

Experience the unique character of Woodstock with a stay in a vacation home rental. Travelers to this welcoming city praise the restaurants, shopping and hiking. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Woodstock

Are you searching for top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Woodstock a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Shenandoah Vineyards (3.8 mi / 6 km)
  • Caverns Country Club (14.3 mi / 23.1 km)
  • Bryce Ski Resort (14.8 mi / 23.8 km)
  • Yogi Bear's Jellystone Park (15.7 mi / 25.3 km)
  • Secret Passage Ranch (8.3 mi / 13.3 km)
  • Cave Ridge Vineyard (9.8 mi / 15.8 km)

Exploring the natural landscape of Woodstock

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Woodstock is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Luray Caverns (15.1 mi / 24.3 km)
  • Massanutten Storybook Trail (10.6 mi / 17.1 km)
  • Shenandoah Caverns (14.5 mi / 23.3 km)
  • The Garden Maze at Luray Caverns (15 mi / 24.1 km)
  • Skyline Caverns (15.6 mi / 25.1 km)
  • Lost River (16.8 mi / 27.1 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 center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Woodstock?
Based on our research, cottages are the most desirable vacation rental type in Woodstock. But of course, everyone's idea of an epic stay isn't the same. Vrbo has vacation homes in a variety of sizes and shapes, so you're sure to find the best fit for your needs.
How much does it cost to rent a vacation rental in Woodstock?
Several things can influence what you'll pay for a vacation rental in Woodstock, like the season, length of stay and type of property. However, all of our vacation homes have something in common --- exceptional value. Just enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Woodstock?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Put in your Woodstock travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to select the features and amenities you want in your rental.
Are there pet-friendly vacation rentals in Woodstock?
You're in luck. There are. You'll have a choice of six stays that welcome pets in Woodstock on Vrbo. Our furry companions also need a break, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where your pooch can get in on the fun.
What are popular rental amenities in Woodstock?
When it comes to rental amenities that people are looking for in Woodstock, a fireplace, a nearby river and a barbecue grill rank highest. With Vrbo vacation homes, there are options to fit your style and taste, whether you're going on a trip with your partner, family members or even pets.
Are there large group vacation rentals in Woodstock?
Take your pick of five Vrbo vacation rentals in Woodstock that can accommodate a group of five or more guests. You'll get all the space and privacy you need to kick back with your nearest and dearest --- and nobody else.
Are there vacation rentals in Woodstock that welcome kids?
With six family-friendly vacation properties available in Woodstock, now is the perfect time to introduce the kids to the pleasures of travel. Simply click on our "Properties good for families" filter to look for stays packed with conveniences perfect for vacationing families, such as dining rooms, swimming pools, entertainment units and bunk beds.
What are the top attractions for families in Woodstock?
Keeping the kids entertained during your Woodstock vacation is child's play with these awesome family-friendly attractions:

  • Shenandoah County Fairgrounds
  • Seven Bends State Park
  • 7 East Gallery

Are there vacation rentals with WiFi in Woodstock?
Whether you want to keep up with the latest news, send some emails or update your social media, there are five vacation homes with WiFi in Woodstock. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Woodstock?
Select your dates and then make use of our filters to view vacation rentals with air conditioning in Woodstock on Vrbo. With five air-conditioned properties available here, you can look forward to a cool and comfy break.
How old do you have to be to rent a vacation rental in Woodstock?
We recommend you check with the Woodstock vacation rental you're looking at on Vrbo as the minimum age differs. However, generally it's 16, 18 or 21.
How long can I rent a vacation rental in Woodstock for?
How long you can book a vacation rental in Woodstock depends on the property. Simply enter your preferred dates to display a list of options offering extended stays. With tons of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Woodstock.
Does Vrbo offer discounts for vacation homes in Woodstock?
In Woodstock, you'll find some great bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're wanting a weekend escape or an extended stay, we offer a host of options to suit your style.

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