Woodstock vacation rentals

We found 1,073 vacation rentals — enter your dates for availability

Discover a selection of 36 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:Nov 14 - Nov 21

Image gallery for Fall into Cozy at Bigfoot Chalet

Exterior
10 out of 10 rating
Exceptional
(13 reviews)

Fall into Cozy at Bigfoot Chalet

Plymouth, VT

28% off
Price is CA $231
CA $2,277 total
includes taxes & fees
Fall into Cozy at Bigfoot Chalet

Find spaces that suit your style

Find out more about Woodstock

Find out more about Woodstock

Why visit Woodstock

  1. Outdoor Adventure: Enjoy skiing, hiking, and various outdoor activities in the stunning mountainous landscape.
  2. Cultural Experiences: Discover historic colleges, houses, and a vibrant local art scene that reflects the town's rich heritage.
  3. Family-Friendly Activities: Engage in a variety of fun outings suitable for all ages, ensuring memorable family vacations.
  4. Charming Neighbourhoods: Explore quaint neighbourhoods with unique shops and inviting atmospheres, perfect for leisurely strolls.
  5. Diverse Accommodations: Choose from cozy cabins to private vacation homes, catering to every traveller's needs.

Popular types of accommodation in Woodstock

Planning a getaway to Woodstock? The excitement begins with selecting the perfect accommodation! Explore an array of options, including houses, cozy cabins, and inviting condos. Whether you're seeking a holiday cottage or a short-term rental, Woodstock offers a variety of vacation rentals to suit your needs. Enjoy transparency, savings, and peace of mind as you find your ideal home away from home!

  • Houses: The top choice for visitors to Woodstock, these homes offer spacious and comfortable accommodations, ideal for families, couples, or groups.
  • Condos: A popular second option, condos provide modern amenities and are often located near local attractions for easy access.
  • Cabins: Perfect for those seeking a rustic escape, cabins offer a charming retreat amidst the natural beauty of Vermont.
  • Apartments: These practical spaces are great for solo travellers or couples looking for a convenient stay.
  • Cottages: A delightful choice for a cozy and intimate getaway, cottages are perfect for enjoying a peaceful stay in Woodstock.**

Top attractions in Woodstock

Woodstock, Vermont, is an ideal destination for adventure enthusiasts, offering a mix of skiing and outdoor activities. Visitors can explore a variety of attractions, including historic colleges, state parks, and historic houses. Whether you're seeking cultural experiences or family-friendly outings, Woodstock provides a perfect blend of activities to suit every traveller's interests.

  1. Quechee Gorge Bridge: A stunning natural canyon located 9.7km from Woodstock, offering breathtaking views and outdoor adventure. Hike along scenic trails and experience the thrill of the gorge's dramatic cliffs.
  2. Dartmouth College: This historic university, situated 20.9km from Woodstock, boasts beautiful architecture and a rich cultural atmosphere. Explore its stunning campus and immerse yourself in its academic heritage.
  3. Billings Farm and Museum: Located within Woodstock, this engaging museum showcases Vermont's rural heritage through interactive exhibits and a working farm. Experience local history and culture up close.

Things to do recommended for couples

Embark on a romantic adventure in Woodstock, Vermont! Hit the slopes at Saskadena Six Ski Area, indulge in baking delights at King Arthur Baking Company, and unwind together at The Strong House Spa for a rejuvenating experience. Perfect for couples seeking relaxation and excitement!

Things to do recommended for families

Your family will love the Upper Valley Aquatic Center for some splashing fun, while the Union Arena Community Center offers exciting ice skating. For a peaceful escape, head to Wilderness Trails, where you can unwind and connect with nature, all within a short drive from Woodstock.

Things to do recommended for groups

Groups visiting Woodstock, Vermont can enjoy a round of golf at the Woodstock Country Club, catch a show at the charming Woodstock Town Hall Theatre, or explore the unique shops at Quechee Gorge Village, located 9.7km away for a delightful day trip.

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

When planning your trip—be it with a group, family, pets, or for an extended stay—it's important to prioritize your preferences while filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Travelling with young children 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, considering how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Woodstock: For many families, a trip isn't truly complete without their furry companion. If this resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels 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 consider adding amenities like a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay in Woodstock

Woodstock, Vermont, offers a delightful blend of adventure and relaxation, perfect for family vacations or romantic getaways. Nestled amidst stunning mountains, this charming city boasts a rich historical vibe and vibrant art scene. Nearby destinations like West Yellowstone enhance the experience with friendly communities and breathtaking scenery. Whether skiing down the slopes or exploring quaint neighbourhoods, Woodstock promises an unforgettable Vermont experience that will become a favourite vacation spot for all visitors.

  • West Woodstock: Nestled in the scenic landscape surrounding Woodstock, West Woodstock is a charming neighbourhood that attracts nature enthusiasts and adventure seekers alike. Renowned for its skiing opportunities, this area is perfect for winter sports lovers, offering access to renowned ski fields and resorts. Beyond skiing, visitors can explore the breathtaking national state parks and serene lakes, making it an ideal destination for outdoor activities year-round. The majestic mountains provide a stunning backdrop for hiking, mountain biking, and photography, ensuring that every traveller leaves with unforgettable memories.
  • Taftsville: Located within the greater Woodstock area, Taftsville is a quaint village known for its picturesque views and rich outdoor experiences. This charming village is popular among those seeking both adventure and tranquillity, with numerous ski fields and resorts nearby for winter sports aficionados. Visitors can explore the stunning canyon gorge and take in the breathtaking views from the iconic bridge that spans it. The tranquil lake in the vicinity also offers opportunities for fishing, kayaking, or simply relaxing in nature, making Taftsville a delightful retreat for all ages.
  • Quechee: Just 8.0km from Woodstock, Quechee is a vibrant city that serves as a hub for adventure and outdoor fun. Known for its excellent skiing facilities, Quechee attracts visitors eager to hit the slopes at its nearby ski resorts. In addition to skiing, the area boasts remarkable natural landmarks, including a beautiful lake and dramatic canyon gorge, perfect for hiking and exploration. The quaint village atmosphere, combined with its stunning landscapes and outdoor activities, makes Quechee an appealing destination for anyone looking to immerse themselves in Vermont's natural beauty.

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 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 simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can change significantly. You might also discover substantial savings by booking a longer stay. To find the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area for you to plan new journeys, refine your existing arrangements, or manage your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover the features of Trip Boards, please visit: https://www.vrbo.com/en-ca/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:

  • 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)
  • Killington Golf Course (13.8 mi / 22.2 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:

  • Marsh-Billings-Rockefeller National Historical Park (1.3 mi / 2 km)
  • Quechee Gorge Bridge (5.6 mi / 9 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)
  • Echo Lake (13.8 mi / 22.2 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 when booking a vacation rental?
When considering a vacation rental in Woodstock, Vermont, a popular area to stay is the picturesque village centre. This charming neighbourhood is known for its quintessential New England architecture and offers a delightful array of boutique shops, restaurants, and art galleries. Staying here puts you within walking distance of top attractions such as the iconic Woodstock Inn and Resort and the serene Marsh-Billings-Rockefeller National Historical Park, which showcases the region's natural beauty and rich history.

Another appealing option is the surrounding areas of Pomfret and South Woodstock, which provide a more tranquil countryside experience. These locations are superb for those seeking a peaceful retreat while still being close to the vibrant village. Here, you can enjoy the stunning landscapes and visit the nearby Billings Farm & Museum, where you can learn about Vermont's rural heritage and engage with farm animals.
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 travelling 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.
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 renting ski accommodations in Woodstock, Vermont, travellers should focus on the areas surrounding the Suicide Six Ski Area and the picturesque village of Woodstock itself. In the vicinity of Suicide Six, visitors can find a range of lodgings, including modern chalets and cosy cabins. Many of these properties offer amenities such as fireplaces, well-equipped kitchens, and hot tubs, ideal for relaxing after a day on the slopes.

Additionally, the village of Woodstock provides a charming backdrop with its historic architecture and local shops. Here, vacation rentals often include elegant inns and spacious homes that feature amenities like private balconies, scenic views, and easy access to the nearby hiking trails and cross-country skiing routes.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular type of rental, with around 32 available throughout the area. These properties provide a charming, spacious environment ideal for families or groups, often featuring multiple bedrooms, well-equipped kitchens, and inviting living areas. Many houses also come with outdoor spaces, such as gardens or patios, superb for enjoying the beautiful Vermont scenery. Additionally, there are several apartments, cottages, chalets, and cabins available, offering a range of choices for travellers seeking a more intimate or rustic experience.
Are there any family house rentals in Woodstock?
In Woodstock, Vermont, visitors will find a variety of family-friendly house rentals—approximately 37 options available throughout the area. The town is renowned for its picturesque landscapes and charming New England architecture, making it an ideal destination for families seeking both adventure and relaxation. Many properties feature spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can play and explore.

The neighbourhood surrounding the village is rich with activities, including easy access to the scenic Marsh-Billings-Rockefeller National Historical Park and the beautiful Ottauquechee River, where families can enjoy hiking, picnicking, and even canoeing. Additionally, some rentals may offer amenities like game rooms and fireplaces, adding to the comfort and enjoyment of your stay.
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, known for its picturesque landscapes and outdoor activities, offers a range of properties that cater to different preferences. Many rentals include amenities such as private pools, relaxing hot tubs, and expansive outdoor spaces, superb for enjoying the serene surroundings after a day of exploring. Some homes may also come equipped with fully stocked kitchens, fire pits, and cozy living areas, making them ideal for family gatherings or a peaceful retreat.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, Vermont, there are several pet-friendly house rentals available, with a total of 23 options to choose from. These vacation homes typically offer a variety of amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces that may include decks or gardens, great for enjoying the picturesque surroundings. Many properties are designed to accommodate both pets and their owners, ensuring a comfortable stay for all.
Are there any remote work vacation rentals in Woodstock?
In Woodstock, Vermont, there are numerous vacation rentals suitable for remote work, with around 39 options available. This picturesque town is not only known for its stunning New England scenery but also offers a tranquil environment ideal for those looking to balance work and leisure. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, and comfortable desks and chairs. Some rentals even include computer monitors to enhance productivity. 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 travellers 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 vacation rental amenities include kitchens equipped with essential appliances such as dishwashers, microwaves, refrigerators, and stovetops. These features allow travellers to prepare their own meals while enjoying the comforts of home. Many rentals are situated in picturesque surroundings, offering a tranquil retreat close to local attractions and the charming village centre.
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 autumn foliage paints the landscape in a dazzling array of colours. This period falls within the peak season, which spans from August to October, attracting visitors keen to experience the stunning natural beauty and partake in various outdoor activities. Hiking trails become particularly inviting, offering breathtaking views of the changing leaves, while the cool, crisp air makes for comfortable exploration.

August can be a bit busier, with summer activities still in full swing, but September strikes the superb balance between pleasant weather and fewer crowds. Daytime temperatures typically hover around the low 20s Celsius, making it ideal for sightseeing and outdoor adventures without feeling too hot.

For those seeking a more budget-friendly option, March presents an excellent opportunity. While it's technically the low season, visitors can enjoy a quieter atmosphere and the charm of early spring as the landscape begins to thaw. It's a wonderful time for peaceful walks and enjoying the tranquil vibe of the town.
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?
In Woodstock, Vermont, visitors can enjoy a number of attractions that showcase the town's charming New England character. The picturesque Woodstock village features the iconic Middle Bridge and the historic Kedron Valley Inn, offering a glimpse into the area's rich history. Nearby, the Marsh-Billings-Rockefeller National Historical Park provides beautiful walking trails and opportunities to learn about conservation and forestry.
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 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 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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