Woodstock holiday homes

We found 1,322 holiday rentals — enter your dates for availability
Discover a selection of 11 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

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Image gallery for Enjoy a nature retreat in this secluded 4 bedroom lodge in Shenandoah,Virginia!

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10 out of 10, Exceptional, (137 reviews)
Exceptional
(137 reviews)

Enjoy a nature retreat in this secluded 4 bedroom lodge in Shenandoah,Virginia!

Shenandoah

8% off
Price is NZ$5,785
for 7 nights, 1 cabin
NZ$826 per night
includes taxes & fees
Enjoy a nature retreat in this secluded 4 bedroom lodge in Shenandoah,Virginia!

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

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:

  • Bryce Ski Resort (14.8 mi / 23.8 km)
  • Yogi Bear's Jellystone Park (15.7 mi / 25.3 km)
  • Shenandoah Vineyards (3.8 mi / 6 km)
  • North Mountain Vineyard and Winery (4.8 mi / 7.7 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 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:

  • 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)
  • Luray Caverns (15.1 mi / 24.3 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 centre.

Frequently asked questions

Where are the best Woodstock ski resort rentals?
For skiing in Woodstock, Virginia, the nearby Massanutten Resort offers a range of rental options that cater to winter sports enthusiasts. In the vicinity of the resort, travellers can find a variety of condos and cabins that provide convenient access to the slopes. Many of these properties come with amenities such as fully equipped kitchens, spacious living areas, and fireplaces, superb for unwinding after a day on the mountain.

The town of Woodstock itself features charming accommodations, including rustic lodges and modern apartments, often equipped with essentials like Wi-Fi and heating. Staying here gives visitors a taste of local culture, with easy access to the quaint downtown area filled with shops and eateries. For those who enjoy exploring, nearby attractions like the George Washington National Forest offer opportunities for hiking and enjoying the stunning natural beauty of the region.
What is the most popular type of holiday rental accomodation in Woodstock?
In Woodstock, holiday houses are the most popular type of holiday rental, with around 36 available in the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas great for enjoying the beautiful surroundings. For those seeking a more rustic experience, several cabins and cottages are also available, offering a charming escape with a more intimate atmosphere. These alternatives often come with unique amenities such as wood-burning stoves and scenic views, making them ideal for nature lovers looking to explore the nearby Shenandoah National Park.
Are there any family house rentals in Woodstock?
In Woodstock, Virginia, there are some family-friendly house rentals available, with around ten options to choose from. This charming town, located in the scenic Shenandoah Valley, offers a delightful mix of outdoor activities and historical sites. Many properties feature spacious living areas, well-equipped kitchens for preparing family meals, and private yards where children can play safely.

Visitors can explore nearby attractions such as the beautiful George Washington National Forest, which is great for hiking and picnicking, or the historic downtown area, where local shops and eateries provide a taste of community life.
Can I rent a holiday home with a pool or hot tub in Woodstock?
In Woodstock, Virginia, there are several holiday homes available for rent that feature pools and hot tubs, suiting those seeking a relaxing getaway. The area offers a mix of charming accommodations, including country houses and modern retreats located in the scenic Shenandoah Valley. Many properties come equipped with private pools, inviting hot tubs, and spacious outdoor areas superb for gatherings or quiet evenings under the stars. Inside, travellers can expect amenities like fully equipped kitchens, comfortable living spaces, and often, picturesque views of the surrounding countryside.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, Virginia, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. The area offers a variety of holiday homes, often equipped with amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, superb for families or groups. Many rentals feature fenced yards or patios, providing a safe and enjoyable environment for pets.

The town is located in the scenic Shenandoah Valley, surrounded by beautiful landscapes and outdoor recreational opportunities. While exploring the region, pet owners can enjoy nearby parks and trails, which are superb for walks and hikes with their pets.
Are there any remote work holiday rentals in Woodstock?
In Woodstock, Virginia, there are plenty of options for remote work holiday rentals, with around 44 properties available. The area is known for its scenic beauty and charming small-town atmosphere, making it a pleasant backdrop for work and relaxation. Many of these rentals come equipped with essential amenities for remote work, such as free Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring that you can stay productive during your stay.

The town offers a variety of accommodations, from cosy cabins to modern homes, often featuring spacious living areas and outdoor spaces to unwind after a day of work. Woodstock's proximity to outdoor attractions, including the George Washington National Forest, provides ample opportunities for hiking and exploring nature during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Woodstock?
In Woodstock, popular holiday rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, as well as onsite parking for convenience. Many properties feature a coffee and tea maker for that essential morning brew, while a fireplace adds a cosy touch, great for chilly evenings. Additionally, outdoor spaces like decks or patios are common, providing a lovely spot to relax and enjoy the surrounding scenery.
When is the best time to visit Woodstock for a holiday rental?
July is the most popular time to visit Woodstock, Virginia, as the summer months from June to August attract many holidaymakers eager to enjoy the region's outdoor charm. This peak season offers a delightful mix of activities, from exploring the scenic George Washington National Forest to attending local festivals that celebrate the area's rich heritage.

During July, visitors can expect warm temperatures ranging from 20 to 30 degrees Celsius, making it ideal for outdoor adventures such as hiking, biking, and picnicking. The vibrant setting during this month is complemented by opportunities to experience the local culture, including farmers' markets and live music events.

For those looking for a more budget-friendly option, December is a wonderful time to consider a visit. The quiet, off-peak season allows for a more serene experience, superb for enjoying the tranquillity of Woodstock during the winter months. You can explore the charming downtown area adorned with festive decorations and partake in seasonal activities without the crowds.

Ultimately, your choice of when to visit Woodstock will depend on whether you prefer the lively summer spirit filled with outdoor fun or the peaceful charm of winter months.
What are the top attractions in Woodstock?
In Woodstock, Virginia, visitors can enjoy a variety of attractions that showcase the area's natural beauty and historical significance. The Shenandoah County Courthouse, located in the heart of downtown, is an excellent example of 19th-century architecture and serves as a focal point for local history. Just a short drive away, the George Washington National Forest offers a wealth of outdoor activities, including hiking, camping, and stunning views of the Blue Ridge Mountains.

For those interested in history, the nearby Museum of the Shenandoah Valley provides an engaging insight into the region's past and features lovely gardens. Additionally, the town is known for its charming Main Street, where visitors can explore local shops, cafes, and antique stores, creating a delightful atmosphere for leisurely strolls.
Are all fees included in the Woodstock holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Woodstock holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Woodstock with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Woodstock holiday homes?
You can find great discounts on holiday homes in Woodstock on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Woodstock holiday home booking on Bookabach?
To find Woodstock holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Woodstock?
A long-stay holiday home in Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Woodstock holiday home?
Book your Woodstock holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Woodstock?
Prices for holiday homes in Woodstock vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Woodstock to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.