Woodstock vacation rentals

We found 1,082 vacation rentals — enter your dates for availability

Discover a selection of 37 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.

Vacation rentals with weekly discounts - Woodstock

Showing deals for:Aug 22 - Aug 29
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Find out more about Woodstock

Find out more about Woodstock

Why visit Woodstock

  1. Charming village atmosphere: Enjoy the picturesque streets of Woodstock filled with quaint shops and local restaurants.
  2. Outdoor adventures: Experience skiing, hiking, and exploring the beautiful state parks and lakes surrounding the area.
  3. Cultural experiences: Discover historical sites and artistic vibes that enrich Woodstock's unique charm.
  4. Family-friendly activities: Engage in various activities suitable for all ages, making it a perfect getaway for families.
  5. Cozy accommodations: Choose from charming vacation rentals, cozy condos, and stylish apartments for a comfortable stay.

Popular types of accommodation in Woodstock

If you’re planning a getaway to Woodstock, you’re in for a treat! This charming destination offers a variety of vacation rentals, including cozy condos, spacious houses, and comfortable apartments. Whether you’re looking for a whole home or a quaint inn, Woodstock has the perfect accommodation to fit your needs. Explore your options for vacation rentals in Woodstock and enjoy a memorable stay in this beautiful Vermont haven.

  • Condos: The top choice for vacation rentals in Woodstock, these modern units offer comfort and convenience with great amenities for travelers.
  • Houses: A popular option for families and groups, these homes provide a cozy atmosphere and ample space for relaxation.
  • Apartments: Ideal for solo travelers or couples, apartments offer a compact yet comfortable living space in the heart of Woodstock.
  • Cabins: Perfect for those seeking a rustic escape, these charming cabins blend cozy interiors with nature's tranquility.
  • Cottages: A favorite for their quaint appeal, cottages provide a charming and intimate setting for a getaway.**

Top attractions in Woodstock

Woodstock, Vermont, is an ideal destination for ski enthusiasts and outdoor adventurers. This charming town offers a variety of attractions, including national and state parks, beautiful lakes, and ski resorts. Travelers can immerse themselves in cultural experiences while enjoying the stunning scenery and outdoor activities that Woodstock has to offer, making it a perfect getaway for those seeking adventure and relaxation.

  1. Quechee Gorge Bridge: Experience stunning outdoor scenery and adventure just 6 miles from Woodstock. The bridge offers breathtaking views of the deep gorge and is perfect for hiking and photography.
  2. Billings Farm and Museum: Located within Woodstock, this museum immerses you in Vermont's rich agricultural history. Explore exhibits and a working farm while enjoying the culture and traditions of the region.
  3. Dartmouth College: Situated 13 miles away, this historic university boasts beautiful architecture and a vibrant academic atmosphere. Stroll through the picturesque campus and soak in the cultural vibe.

Things to do recommended for couples

Escape to Woodstock, Vermont, for a romantic getaway. Enjoy the thrill of skiing at Okemo Mountain Resort, rejuvenate at the Strong House Spa, and embrace adventure at the Sunrise Village Triple Ski Lift. Each experience offers a perfect blend of relaxation and excitement for couples.

Things to do recommended for families

Your family will love the Upper Valley Aquatic Center for some splashing fun, the Union Arena Community Center for exciting ice skating, and Wilderness Trails for a relaxing day in nature. These local experiences in and around Woodstock promise adventure, wellness, and unforgettable memories together!

Things to do recommended for groups

Groups visiting Woodstock, Vermont, can enjoy a show at the Woodstock Town Hall Theatre, explore shops at Quechee Gorge Village just 6 miles away, and play a round of golf at the scenic Woodstock Country Club for an unforgettable local experience.

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, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many families, a trip isn’t truly fulfilling without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many pet-friendly properties offer amenities like 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 with special offers 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 in Woodstock

Woodstock, Vermont, offers an enchanting vacation experience with its charming village, vibrant downtown, and stunning wooded mountainsides. Explore the natural beauty of Central Vermont while indulging in outdoor adventures like skiing and hiking. The area is known for its historical sites and artistic vibes, making it a perfect blend of relaxation and exploration. With its family-friendly atmosphere and friendly locals, Woodstock promises an unforgettable getaway in the heart of New England.

  • Killington: Located 14 miles from Woodstock, Killington is a haven for adventure seekers and winter sports enthusiasts. Known for its expansive ski resorts, Killington attracts visitors looking for thrilling skiing and snowboarding experiences. The picturesque landscape includes stunning mountains, serene lakes, and lush valleys, perfect for year-round outdoor activities. In addition to skiing, you can explore hiking trails, mountain biking, and scenic gondola rides that offer breathtaking views of the Green Mountains. After a day of adventure, unwind at local eateries that serve hearty mountain fare.
  • Quechee: Just 5 miles from Woodstock, Quechee is a charming village renowned for its natural beauty and outdoor recreation. It features the stunning Quechee Gorge, often referred to as Vermont's "Grand Canyon," where visitors can hike along scenic trails or enjoy a picnic by the river. Quechee is also a popular destination for skiing, with easy access to ski fields and resorts. Don’t miss the chance to visit local artisanal shops, galleries, and the Quechee Balloon Festival if you're there during the summer. The combination of outdoor adventure and quaint village charm makes Quechee a must-visit.
  • White River Junction: Located 10 miles from Woodstock, White River Junction is a vibrant town that offers a mix of history and outdoor adventure. Known for its historic college and thriving arts scene, visitors can explore unique shops, galleries, and theaters. The area is also a gateway to outdoor activities, including skiing and hiking. The nearby lakes and the scenic beauty of the canyon gorge provide perfect backdrops for exploration. Whether you’re interested in history, culture, or outdoor fun, White River Junction presents a diverse range of attractions that cater to every traveler.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 HighModerately Low
August66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
September59.7°F (15.4°C)Light RainMostly SunnySlightly HighAverage
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 simple

Are you aiming to save on your upcoming journey? Being open to different travel dates can really help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort 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. Being the organizer definitely has its perks! When you join our travel rewards program, OneKey, you’ll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash™ on eligible reservations. Sign up today and begin enjoying the savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new adventures, refine your existing itineraries, or manage your reservations. Your saved and booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

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

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:

  • Saskadena Six Ski Area (3 mi / 4.9 km)
  • Sugarbush Farm (3.8 mi / 6.1 km)
  • Quechee State Park (5.5 mi / 8.8 km)
  • Upper Valley Aquatic Center (8.8 mi / 14.2 km)
  • Killington Golf Course (13.8 mi / 22.2 km)
  • Killington Resort (13.9 mi / 22.3 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:

  • Marsh-Billings-Rockefeller National Historical Park (1.3 mi / 2 km)
  • 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)
  • Amherst Lake (13.3 mi / 21.4 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 when booking a vacation rental?
West Woodstock is one of the more popular locations to find a vacation property in Woodstock. Searching for some fun places to see here? Check out Union Arena Community Center and Five Elm Arches.
What is the most popular type of vacation rental accommodation in Woodstock?
Cottages are the most popular style of vacation rental in Woodstock, according to our data. Even if you have something bigger or smaller in mind, Vrbo has vacation homes in a variety of shapes and sizes. Browse our options to find your perfect pad.
How much does it cost to rent a vacation rental in Woodstock?
Several things can influence the price of a vacation rental in Woodstock, such as the type of property, length of stay and season. But, all of our vacation homes have something in common — exceptional value. Just add 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 style and size of the property will determine the cost of your beachside vacation rental. Type in your Woodstock travel dates to view your available options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to pick the amenities and features you need.
Are there pet-friendly vacation rentals in Woodstock?
Yes. There are. Take your pick of 41 vacation rentals that welcome pets in Woodstock on Vrbo. Our cuddly best friends also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to book a pad where your puppy dog can join in the fun.
Can I rent a house with a pool in Woodstock?
Add a whole new level of fun to your vacation by booking your family into one of the seven houses with a private pool in Woodstock. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your downtime splashing and playing in a swimming pool that’s just for you.
What are popular rental amenities in Woodstock?
When it comes to rental amenities that people are searching for in Woodstock, a swimming pool, a lake view and a firepit rank the highest. With Vrbo vacation rentals, you’ll find options to match your style and taste, whether you’re planning to get away with friends, family or even pets.
Are there large group vacation rentals in Woodstock?
Woodstock has six vacation homes that can cater to 10 or more guests. These stays come with the space you need to share good times with loved ones.
Are there vacation rentals in Woodstock that welcome kids?
Gather your whole family for fun-filled adventures in Woodstock at one of our 41 family-friendly properties. Lots of these stays offer conveniences that are ideal for trips with youngsters, such as laundries, extra bedrooms and private pools. Just click on the “Properties good for families” filter and pick out your favorite.
What are the top attractions for families in Woodstock?
There are plenty of exciting things to see and do with the family in Woodstock, including:

  • Woodstock Country Club
  • Dana House Museum
  • Taftsville Covered Bridge

Are there one-bedroom vacation rentals in Woodstock?
You can pick from six one-bedroom rentals in Woodstock. Whether you’re looking for a townhouse or an upmarket condo, our one-bedroom rentals are just right if you don’t require tons of space. One of the perks of having your own pad? You won’t ever have to share your getaway with strangers.
Can I find two-bedroom vacation rentals in Woodstock?
Woodstock has four two-bedroom vacation rentals to pick from. Discover a vacation home with all the space and comfort you want at a price you’ll love on Vrbo.
Are there vacation rentals with WiFi in Woodstock?
Whether you want to keep up with the latest news, look over emails or surf social media, there are 18 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?
There are 25 Vrbo vacation homes with air conditioning in Woodstock providing that cool, cool breeze and extra element of comfort. Simply enter your preferred travel dates and then use our handy filter tool to look for properties with air conditioning.
How old do you have to be to rent a vacation rental in Woodstock?
It’s advisable to check with the Woodstock vacation home you’re looking at on Vrbo as the minimum age differs. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Woodstock for?
The amount of time you can stay in a Woodstock vacation home for is down to each property. Simply put in your preferred travel dates to view available options that offer extended stays. They include the things you need to make your extended break more convenient and comfortable, such as kitchens and backyards. Some properties might also offer weekly or monthly discounts, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Woodstock?
Whether you’ve got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fantastic bargains and discounts on Vrbo. From mini stays to extended getaways, we’ve got the ideal space for your next Woodstock escape.

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