Woodstock vacation rentals

We found 1,095 vacation rentals — enter your dates for availability

Discover a selection of 29 homes and other vacation rentals in Woodstock that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as a fireplace and a washer and dryer. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Woodstock

Why visit Woodstock

  • Scenic Outdoor Adventures: Enjoy skiing, hiking, and exploring the beautiful Vermont countryside.
  • Charming Historical Sites: Discover the quaint town's rich history through its historic landmarks and bridges.
  • Family-Friendly Activities: Engage in various excursions suitable for all ages, making it perfect for family vacations.
  • Diverse Vacation Rentals: Choose from cozy homes, modern condos, or rustic cabins for a comfortable stay.
  • Vibrant Local Atmosphere: Experience friendly locals and a lively atmosphere during your visit.

Popular types of accommodation in Woodstock

Discover the charm of Woodstock, VT, with a variety of vacation rentals to suit your needs. Whether you're looking for cozy houses, modern condos, or rustic cabins, we have the perfect place for your stay. Explore our selection of Woodstock rentals and find the ideal VT seasonal rental for your getaway. Experience the beauty of Vermont while enjoying the comfort and convenience of your own home away from home.

  • Houses: The top choice for visitors, these spacious homes offer a perfect retreat for families, friends, or couples seeking comfort and privacy in Woodstock.
  • Condos: A popular option, condos provide modern amenities and often stunning views, ideal for those wanting a blend of convenience and style.
  • Cabins: Nestled in nature, cabins offer a cozy and rustic experience, perfect for those looking to unwind in the great outdoors.
  • Cottages: Charming and quaint, cottages in Woodstock provide a delightful escape with a homey feel.
  • Apartments: For a more urban experience, apartments are a great choice, offering easy access to local attractions while maintaining a comfortable vibe.**

Top attractions in and around Woodstock

Woodstock, Vermont, is an ideal destination for adventure seekers and outdoor enthusiasts, offering a range of activities from skiing to exploring local parks. Visitors can discover captivating points of interest such as national parks, historic universities, and charming bridges. With a diverse array of attractions, Woodstock caters to families, culture lovers, and those seeking memorable experiences in the great outdoors.

  • Quechee Gorge Bridge: A stunning canyon located 6 miles from Woodstock, the Quechee Gorge Bridge offers breathtaking outdoor scenery and adventure. Experience hiking trails with picturesque views of the gorge, making it a perfect spot for nature enthusiasts.
  • Dartmouth College: Situated 13 miles away, Dartmouth College is a prestigious historic university known for its rich cultural vibes. Explore the beautiful campus, which features classic architecture and vibrant student life.
  • Billings Farm and Museum: Located within Woodstock, this engaging museum showcases rural Vermont's agricultural history. With its interactive exhibits and farm animals, it provides a unique cultural experience for visitors of all ages.

Things to do recommended for couples

For a romantic getaway in Woodstock, explore the snowy slopes of Killington Resort, just 14 miles away, or hit the beautiful trails at Saskadena Six Ski Area right in town. Don't forget to indulge in delicious treats at King Arthur Baking Company, a must-visit 12 miles away.

Things to do recommended for families

Your family will have a blast at the Upper Valley Aquatic Center, just 9 miles from Woodstock, offering fun water activities. Enjoy ice skating at the Union Arena Community Center in Woodstock, or visit Maple Lanes, a thrilling arcade adventure zone located 20 miles away.

Things to do recommended for groups

Explore Quechee Gorge Village for unique shopping, enjoy a show at the Woodstock Town Hall Theatre for a cultural experience, and hit the greens at the Woodstock Country Club for a fun day of golf with your group.

*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

When planning your trip, whether you're traveling with a group, with family, bringing along pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions for a more enjoyable experience.
  • Taking your pets with you to Woodstock: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer 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 that offer 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Woodstock

Woodstock, Vermont, offers a charming blend of rustic luxury and outdoor adventure, perfect for your vacation. Explore the quaint town's historical sites, enjoy family-friendly excursions, and take in the stunning Vermont countryside. During the warmer months, immerse yourself in the vibrant atmosphere filled with friendly locals and scenic views. Nearby areas also invite exploration, making Woodstock an ideal base for your journey through this picturesque region.

  • White River Junction: Located about 10 miles from Woodstock, White River Junction is a vibrant city that serves as a gateway to adventure. Known for its outdoor experiences, visitors flock here for skiing at nearby resorts and exploring the stunning landscapes. Notable attractions include the historic college university, which adds a touch of culture, and the scenic canyon gorge. The iconic bridge spanning the river offers picturesque views and great photo opportunities, making it a perfect stop for those looking to combine nature with urban charm.
  • Quechee: Just 5 miles from Woodstock, Quechee is a charming town renowned for its beautiful outdoor settings and adventure activities. Visitors can enjoy skiing at the local ski resorts or relax by the serene lake, which is perfect for fishing or picnicking. The breathtaking canyon gorge is a must-see, offering stunning views and hiking opportunities. The town’s picturesque bridge is also a highlight, providing a great spot for photography and enjoying the tranquil surroundings.
  • Hanover: Situated approximately 13 miles from Woodstock, Hanover is a hub of culture and outdoor adventure. Home to a prestigious historic college university, this city offers a rich educational experience. Outdoor enthusiasts can explore ski fields or take part in various recreational activities around the nearby mountains and lakes. The blend of culture and adventure makes Hanover a unique destination, where visitors can immerse themselves in both the academic atmosphere and the natural beauty that surrounds the area.

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 in July and September to October, while off-peak times, like February to April tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.6°F (-6.9°C)Light RainMostly CloudyAverageModerately High
February21.6°F (-5.8°C)Light RainMostly CloudySlightly LowModerately High
March29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage
April42.1°F (5.6°C)Light RainMostly CloudySlightly LowModerately Low
May55.2°F (12.9°C)Light RainMostly SunnyAverageModerately Low
June62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
July68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
August66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
September59.7°F (15.4°C)Light RainMostly SunnySlightly HighModerately Low
October48.0°F (8.9°C)Light RainMostly CloudySlightly HighAverage
November35.4°F (1.9°C)Light RainMostly SunnyAverageAverage
December26.8°F (-2.9°C)Light RainMostly CloudyAverageModerately High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can really help, as prices often vary. Additionally, booking a longer stay typically allows you to enjoy significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Plan your group trip by booking an eligible Vrbo and earn OneKeyCash on the full reservation. It truly rewards you to take on the role of planner. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on qualifying bookings. Sign up today and begin saving.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for planning new trips, managing your existing plans, or organizing your reservations. Your saved or booked properties are categorized into Potential, Upcoming, or Current Trips for easy reference. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The historic city of Woodstock awaits you

Enjoy the area's architecture, history and museums and make a vacation rental your home during your stay in Woodstock. Renowned for its riverfront, restaurants and shopping, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Woodstock

Are you hoping to find top things to see and do while you're in the area? Venture out of your cozy vacation rental and experience everything that Woodstock has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Okemo Mountain Resort (18.3 mi / 29.5 km)
  • Saskadena Six Ski Area (3 mi / 4.9 km)
  • Sugarbush Farm (3.8 mi / 6.1 km)
  • Quechee Ski Hill (4.4 mi / 7 km)
  • Quechee State Park (5.5 mi / 8.8 km)
  • Upper Valley Aquatic Center (8.8 mi / 14.2 km)

Exploring the natural features in Woodstock

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Woodstock is a great place to get out in nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Quechee Gorge Bridge (5.6 mi / 9 km)
  • Lakota Lake (7.7 mi / 12.4 km)
  • Silver Lake State Park (8.9 mi / 14.3 km)
  • Mount Ascutney (12.9 mi / 20.7 km)
  • Echo Lake (13.8 mi / 22.2 km)
  • Lake Rescue (15.1 mi / 24.2 km)

How to get to and around Woodstock

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.5 mi (16.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Springfield, VT (VSF-Hartness State), which is 19.4 mi (31.3 km) away.

Frequently asked questions

What is the best area to stay in Woodstock, Vermont, United States of America when booking a vacation rental?
When looking for the best area to stay in Woodstock, Vermont, you'll want to consider the charming village itself, which offers a delightful blend of picturesque scenery and local attractions. This area is known for its beautifully preserved 19th-century architecture and a vibrant community atmosphere. The village features a range of vacation rentals, from cozy cottages to luxurious inns, providing plenty of options for travelers.

One of the top attractions nearby is the Billings Farm and Museum, where you can immerse yourself in the history of Vermont's agricultural heritage. It's a fantastic place for families, offering engaging exhibits and activities. Additionally, the stunning Marsh-Billings-Rockefeller National Historical Park is just a short distance away, great for outdoor enthusiasts who enjoy hiking and exploring nature trails.

Another appealing area is the surrounding countryside, which boasts gorgeous landscapes and lovely views, ideal for those seeking a tranquil retreat. This region also has a good variety of vacation rentals, allowing visitors to connect more with the natural beauty of Vermont while still being close to the village's amenities.
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.
Where are the best Woodstock ski resort rentals?
For the best ski resort rentals in Woodstock, Vermont, travelers should focus on the area surrounding the Killington Ski Resort, which is just a short drive away. The town of Woodstock itself offers a picturesque setting with charming accommodations, including cozy lodges and upscale condos that often feature amenities like fireplaces, hot tubs, and fully equipped kitchens, ideal for relaxing after a day on the slopes.

In addition to the Killington area, the nearby Pico Mountain is another great spot for skiing, and rentals in the surrounding areas such as Mendon and Bridgewater provide easy access to both ski resorts. Many of these properties come with convenient features like ski storage, outdoor decks with mountain views, and sometimes even access to community amenities like pools or fitness centers.

Travelers can also enjoy the quaint downtown of Woodstock, which is known for its unique shops, fine dining, and cultural attractions like the Billings Farm and Museum. Properties in or around downtown often boast rustic charm, with features such as hardwood floors, spacious living areas, and proximity to local eateries and shops.

For those looking to explore beyond skiing, the beautiful scenery of the Green Mountains offers ample opportunities for snowshoeing and hiking. See all ski-in-/ski-out rentals in Woodstock.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular rental option, with about 28 available throughout the picturesque area. Many of these homes are situated in charming neighborhoods, providing a cozy atmosphere that blends well with the town's scenic beauty. Most vacation houses come equipped with amenities such as fully stocked kitchens, spacious living rooms, and outdoor patios or decks, superb for enjoying the tranquil surroundings. Additionally, there are several apartments, cottages, chalets, and cabins that cater to various traveler preferences, offering great experiences.
Are there any family house rentals in Woodstock?
In Woodstock, Vermont, there are numerous family-friendly house rentals—about 31 available throughout the area. This charming town is known for its picturesque landscapes and outdoor activities, making it an excellent choice for families. Many of the homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to enjoy. Amenities such as Wi-Fi and laundry facilities are commonly found, adding to the convenience of your stay.

Visitors can explore the beauty of the surrounding Green Mountains, with opportunities for hiking and biking nearby. Additionally, the town is home to attractions like the Billings Farm and Museum, where families can learn about the region's agricultural history.
Can I rent a vacation home with a pool or hot tub in Woodstock?
In Woodstock, Vermont, there are several vacation homes available for rent that feature pools and hot tubs. This charming town is known for its picturesque landscapes and vibrant community, making it an appealing destination for travelers seeking relaxation and outdoor activities. Many of the rental properties come equipped with private pools, hot tubs, and spacious outdoor areas superb for enjoying the serene surroundings. Inside, guests can typically expect modern amenities such as fully equipped kitchens, cozy living spaces, and comfortable bedrooms, ensuring a pleasant stay.
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.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, Vermont, there are numerous pet-friendly house rentals available, with about 20 options to choose from. Travelers can expect a variety of amenities in these properties, including spacious living areas, fully equipped kitchens, and cozy fireplaces, superb for relaxing after a day of exploring the stunning surroundings. Many rentals also feature outdoor spaces such as decks or gardens, providing ample room for pets to enjoy the fresh air.

The picturesque town of Woodstock is known for its charming New England architecture and proximity to beautiful natural attractions. The Marsh-Billings-Rockefeller National Historical Park offers scenic trails and open spaces where pets are welcome, allowing for enjoyable hikes and leisurely walks. Additionally, the nearby Ottauquechee River provides opportunities for outdoor activities, such as kayaking and fishing, making it an excellent destination for pet owners who love the outdoors.
Are there any remote work vacation rentals in Woodstock?
In Woodstock, Vermont, there are numerous remote work vacation rentals available, with around 38 options to choose from. This picturesque town offers a charming atmosphere, making it ideal for combining work and leisure. Many properties come equipped with reliable Wi-Fi, allowing for seamless connectivity, as well as additional amenities such as printers available for booking, ensuring that remote work needs are met.

Travelers can expect cozy accommodations that often feature dedicated workspaces, comfortable living areas, and full kitchens for preparing meals during their stay. The scenic surroundings also provide opportunities for relaxation after work hours, with nearby hiking trails and the scenic Ottauquechee River offering a peaceful retreat. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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.
What are popular rental amenities in Woodstock?
In Woodstock, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, which provide a lovely outdoor space for relaxation or dining al fresco while enjoying the scenic surroundings. Onsite parking is commonly available, making it convenient for those traveling by car. Additionally, rentals often come with coffee and tea makers for a cozy start to the day, and fireplaces are a favorite amenity, creating a warm and inviting atmosphere, especially during the colder months.
When is the best time to visit Woodstock for a vacation rental?
September is the most popular time to visit Woodstock, Vermont, as the vibrant fall foliage begins to paint the landscape in stunning hues of red, orange, and gold. This period, extending from late August through October, attracts travelers looking to immerse themselves in the natural beauty of the area while enjoying outdoor activities like hiking and scenic drives.

During these months, the weather is typically mild, with temperatures ranging from the high 50s to mid-70s Fahrenheit, making it great for sightseeing and exploring the charming downtown area. Visitors can stroll along quaint streets, visit local shops, and partake in seasonal events that highlight the town's rich cultural heritage.

For those seeking a more budget-friendly experience, March is a wonderful option to consider. While it falls in the low season, early spring offers unique opportunities for skiing and snowshoeing in the nearby mountains, and you can enjoy the tranquility of a quieter town before the tourist rush begins.
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, Vermont, United States of America?
In Woodstock, Vermont, visitors can take part in a charming blend of natural beauty and historic attractions. The picturesque Woodstock Village features quaint shops, local eateries, and the iconic Norman Williams Public Library, showcasing classic New England architecture. Nearby, the Marsh-Billings-Rockefeller National Historical Park offers scenic trails and a glimpse into the region's conservation history through its beautifully maintained gardens and woodlands.

For those interested in local culture, the Billings Farm & Museum provides an engaging experience with farm animals and exhibits about Vermont's agricultural heritage. The area around Kedron Valley is known for its stunning landscapes, and vacation rentals here often provide easy access to outdoor activities like hiking and biking.

Additionally, the nearby Pomfret area offers serene countryside views and the chance to explore the scenic Quechee Gorge, adding to the region's appeal for nature enthusiasts.
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.

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