Woodstock vacation rentals

We found 186 vacation rentals — enter your dates for availability

Discover a selection of 16 homes and other vacation rentals in Woodstock that are perfect for your trip. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, such as a hot tub and garden. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Woodstock

Why visit Woodstock

  • Family-friendly activities: Enjoy a variety of attractions perfect for families, from urban parks to community events.
  • Charming local culture: Experience warm community vibes with unique shops and cozy cafes lining walkable streets.
  • Outdoor adventures: Explore nearby parks for recreational activities and connect with nature.
  • Diverse accommodations: Choose from charming vacation homes, modern apartments, and stylish condos for a comfortable stay.
  • Engaging events: Participate in local potlucks and other community gatherings for a unique cultural experience.

Popular types of accommodation around Woodstock

Planning a getaway to Woodstock? The excitement begins with selecting your perfect accommodation. From charming houses to modern apartments and stylish condos, Woodstock offers a variety of options to suit every traveler. Explore the best Woodstock apartments or check out new apartments in nearby Portland for even more choices. No matter where you stay, you’ll find comfort and convenience to make your trip unforgettable.

  • Houses: The top choice for visitors in Woodstock, offering spacious and comfortable settings for families, friends, or couples.
  • Apartments: A popular option for those seeking convenient and modern living spaces during their stay in Woodstock.
  • Condos: Ideal for travelers desiring a blend of luxury and community amenities in Woodstock.
  • Cottages: Charming and cozy retreats perfect for a relaxing getaway in the picturesque surroundings of Woodstock.
  • Cabins: A favorite among nature lovers, providing a rustic experience close to the great outdoors in Woodstock.**

Top attractions near Woodstock

Woodstock in Portland, Oregon, is perfect for family vacations and outdoor adventures. Visitors can enjoy urban parks, modern colleges, and event venues, making it an ideal spot for those seeking a mix of city life and nature. Whether you're exploring the vibrant local scene or engaging in family-friendly activities, Woodstock offers a variety of attractions that promise enjoyable experiences for everyone.

  • Oregon Convention Center: Located 4 miles from Woodstock, this vibrant venue hosts a variety of events, from trade shows to conferences, making it a hub for business and networking in Portland.
  • Oregon Health and Science University: Also 4 miles away, this modern university offers a unique blend of education and healthcare, showcasing cutting-edge research and beautiful architecture in a lively urban setting.
  • Tom McCall Waterfront Park: A 4-mile distance from Woodstock, this picturesque urban park features trails, gardens, and stunning river views, perfect for families and outdoor enthusiasts to enjoy recreational activities.

Things to do recommended for couples

Planning a romantic getaway in Woodstock? Enjoy live music at McMenamins Crystal Ballroom, take a scenic ride on the Portland Aerial Tram, or share a delightful wine tasting at Abbey Creek Winery. Each offers a unique experience perfect for couples looking to connect and explore together.

Things to do recommended for families

Families visiting Woodstock can enjoy exciting activities like catching a game at the Moda Center, exploring the fun rides at Oaks Amusement Park, or relaxing in the serene Westmoreland Park. Each location offers unique vibes, perfect for creating lasting memories together.

Things to do recommended for groups

Explore the vibrant Lloyd Center for shopping and entertainment, visit Powell's City of Books for a literary adventure, and catch a show at the Keller Auditorium for a taste of local culture. These activities offer fun and memorable experiences for your group in Woodstock.

*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 around Woodstock

When traveling with a group, family, or pets, or if you're seeking longer stays, it's important to prioritize your preferences during your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and plenty more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Woodstock: For many families, a vacation isn't truly complete without their furry companion. If this resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone 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 right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Woodstock

Woodstock, a charming neighborhood in Portland, Oregon, offers a delightful mix of family-friendly activities and outdoor adventures. Here, you’ll find walkable streets lined with unique shops, cozy cafes, and community potlucks that create a warm, welcoming atmosphere. Explore nearby parks and enjoy the vibrant local culture, making Woodstock the perfect destination for those seeking both relaxation and connection with friendly locals.

  • Portland: As a thriving metropolis, Portland is a cultural hub that offers a diverse range of experiences. Nestled in the Pacific Northwest, Woodstock is part of this vibrant city. Portland is known for its family-friendly atmosphere and outdoor adventures, making it an ideal destination for travelers of all ages. Popular activities include visiting the city’s renowned shopping centers and catching live events at various arena entertainment facilities. Local landmarks such as the stadium and sports facilities draw sports enthusiasts, while the nearby national state park offers a chance to immerse yourself in nature's beauty.
  • Downtown Portland: Located just 4 miles from Woodstock, Downtown Portland is an energetic neighborhood that buzzes with life. Here, visitors can indulge in a family-friendly, city-themed, and entertainment-focused experience. The area is home to numerous theaters and educational venues, making it a great place for culture enthusiasts. Attractions include a major stadium and a bustling event conference venue, ensuring there’s always something happening. Stroll through the streets to discover unique shops, art installations, and vibrant food scenes, all while enjoying the urban landscape.
  • Mt. Scott-Arleta: Just 0.7 miles from Woodstock, Mt. Scott-Arleta is a charming neighborhood that offers a perfect blend of city and outdoor experiences. Families and outdoor lovers will appreciate the local parks and recreational areas that invite leisurely walks and picnics. The shopping areas and educational facilities cater to various interests, while the neighborhood is punctuated by inviting urban parks and a welcoming community feel. Whether you’re exploring the local shops or enjoying a day at the beach, Mt. Scott-Arleta promises a delightful experience.

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can 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 rental. We're here to help you find the best options for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly area where you can easily create new trips, resume planning from where you last left off, or view and sort your travel arrangements. You'll find your saved or booked properties neatly organized into sections for Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Woodstock?
In Woodstock, vacation houses are the most popular type of rental, with about 15 available throughout the area. These properties often provide spacious living arrangements ideal for families or groups, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation. Additionally, there are several apartments and cottages scattered around, offering a more intimate and cozy atmosphere.
How much does it cost to rent a vacation home in Woodstock?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Woodstock to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Woodstock vacation house rentals?
You can find great discounts on house rentals in Woodstock on Vrbo, 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.
What are popular rental amenities in Woodstock?
In Woodstock, vacation rentals typically offer a range of popular amenities that enhance the guest experience. Most properties feature fully equipped kitchens, allowing travelers to prepare their own meals and enjoy dining at home. Many rentals also include coffee and tea makers for that convenient morning boost. Onsite parking is commonly available, making it easy for guests with vehicles. Outdoor space is another highlight, with decks or patios where guests can relax and take in the picturesque surroundings. Additionally, many rentals are pet-friendly, accommodating travelers who wish to bring their furry companions along.
Can I find family house rentals in Woodstock?
In Woodstock, Oregon, there are several family-friendly house rentals available, totaling around 12 options for those seeking accommodations. This charming town is surrounded by beautiful natural scenery, with easy access to outdoor activities and local attractions. Many of these properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and explore.

Visitors will appreciate amenities such as Wi-Fi for staying connected, air conditioning for comfort, and sometimes even game rooms or private yards for added entertainment. The nearby parks and hiking trails offer fantastic opportunities for family outings, while the local community exudes a friendly setting.
Are there any Woodstock vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodstock with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
Can I book pet-friendly vacation rentals in Woodstock?
In Woodstock, travelers can find a variety of pet-friendly vacation rentals, with around twelve options available to choose from. Many of these rentals come equipped with amenities such as spacious backyards, outdoor patios, and cozy living areas, making them ideal for families or groups traveling with pets. Some properties may also offer features like fully equipped kitchens, laundry facilities, and Wi-Fi, ensuring a comfortable stay.

The neighborhood itself is known for its natural beauty, with nearby parks providing ample opportunities for outdoor activities with pets. Local points of interest often include trails for hiking and areas for picnicking, allowing guests to enjoy the scenic surroundings while accommodating their furry friends.
Can I find long-stay vacation rentals in Woodstock?
A long-stay vacation rental in Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Woodstock for a vacation rental?
The best time to book a vacation rental in Woodstock is during the peak season, which runs from June to August. This vibrant period is particularly popular among families and outdoor enthusiasts who flock to the area to enjoy its picturesque landscapes and a variety of recreational activities. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, visitors can comfortably explore the serene lakes and lush trails that surround this charming town.

July stands out as the most popular month for travelers, offering a lively option filled with festivals, outdoor concerts, and community events. This is an ideal time to soak in the local culture while enjoying activities such as hiking, biking, or simply relaxing by the water.

If you're looking for a more budget-friendly option, consider visiting in December. While this month falls outside the main tourist season, it offers great experiences, such as the tranquility of winter scenery and opportunities for cozy indoor activities. You can enjoy a peaceful retreat and take advantage of lower rental rates, all while appreciating the beauty of Woodstock in its quieter months.

Ultimately, the best time to visit Woodstock depends on your preference for vibrant summer adventures or a peaceful winter getaway.
Are there any remote work vacation rentals in Woodstock?
In Woodstock, Oregon, there are 18 remote work-friendly vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these rentals feature dedicated workspaces, such as desks and comfortable chairs, ensuring a productive environment. Wi-Fi is typically included, allowing for reliable internet access throughout your stay.

The area is known for its scenic beauty, with nearby attractions such as the stunning Cascade Range and various hiking trails. Travelers can expect accommodations that often include amenities like fully equipped kitchens, outdoor spaces for relaxation, and cozy living areas to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Woodstock vacation rental?
Book your Woodstock vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodstock, Oregon, United States of America?
In Woodstock, Oregon, visitors can enjoy a variety of attractions that showcase the area's charm and community spirit. The neighborhood is known for its beautiful parks, such as Woodstock Park, which features walking paths, a playground, and sports facilities, making it a great spot for families and outdoor enthusiasts.

Nearby, the Reed College campus offers picturesque grounds and the renowned Reed College Canyon, where visitors can explore nature trails and enjoy the serene environment. The local area is also home to a range of shops and eateries along SE Woodstock Blvd, providing a taste of local culture and cuisine.

For those interested in arts and culture, the nearby Southeast Portland neighborhoods feature vibrant galleries and music venues, offering additional entertainment options.
Can I change or cancel my Woodstock home rental booking on Vrbo?
To find Woodstock vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Woodstock vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

More Vacation Ideas