Woodstock vacation rentals

We found 1,098 vacation rentals — enter your dates for availability

Discover a selection of 31 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:Jun 12 - Jun 19

Image gallery for "The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Exterior
9.8 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Plymouth

8% off
Price is $432
$3,022 for 7 nights
All fees included
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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Find out more about Woodstock

Why visit Woodstock

  • Outdoor Adventures: Enjoy skiing in winter and hiking in summer amidst stunning mountain views.
  • Charming Woodstock Village: Explore delightful shops and dining options in the heart of the village.
  • Rich History: Visit historic houses and local attractions that showcase the town's cultural heritage.
  • Family-Friendly Festivals: Experience vibrant festivals that cater to all ages, fostering community spirit.
  • Diverse Accommodations: Choose from cozy cabins to modern condos for a comfortable stay in scenic surroundings.

Popular types of accommodation in Woodstock

If you're looking for the perfect getaway, Woodstock has a variety of accommodation options to suit your needs. From charming houses and cozy cabins to modern condos, there's something for everyone. Whether you're seeking a seasonal rental in the beautiful Vermont countryside or a stay at the iconic Woodstock Inn, our platform ensures you find the ideal spot for your vacation. Explore the best Woodstock rentals and make your trip unforgettable.

  • Houses: The top choice for travelers to Woodstock, these spacious homes offer comfort and privacy, perfect for families and groups.
  • Condos: A popular option for those seeking modern amenities, condos provide a convenient and stylish stay close to local attractions.
  • Cabins: Ideal for nature enthusiasts, these cozy retreats offer a rustic charm and a peaceful escape in the woods.
  • Apartments: A practical choice for solo travelers or couples, apartments provide a home-like environment with essential amenities.
  • Cottages: Charming and quaint, cottages offer a delightful retreat for those looking for a cozy and intimate atmosphere.**

Top attractions in and around Woodstock

Woodstock, Vermont, is perfect for outdoor adventures, offering skiing and various activities for all ages. Key attractions include the local medical center, scenic national state parks, and historic houses, providing a blend of culture and outdoor experiences. Don't miss exploring Woodstock Village for charming shops and dining options. For a comfortable stay, consider vacation rentals in the area to fully enjoy your visit.

  • Billings Farm and Museum: This charming museum showcases Vermont's agricultural history with interactive exhibits, farm animals, and historic buildings. It's a perfect spot for those interested in culture and heritage.
  • Quechee Gorge Bridge: Spanning a stunning gorge, this bridge offers breathtaking views and opportunities for outdoor adventures like hiking and photography. It's a must-visit for nature enthusiasts.
  • Dartmouth-Hitchcock Medical Center: While primarily a healthcare facility, it also serves the community with family-friendly events and health programs, making it a unique blend of business and community vibes.

Things to do recommended for couples

Woodstock, Vermont, offers charming experiences for couples. Take a scenic walk along the Kedron Brook, explore the quaint shops in the village, and indulge in a cozy dinner at a local bistro. Don't miss the stunning views from Mount Tom for a perfect romantic sunset.

Things to do recommended for families

Families will love exploring the picturesque Billings Farm & Museum, where they can learn about Vermont's rural heritage. Enjoy a scenic hike along the Marsh-Billings-Rockefeller National Historical Park trails or visit the charming shops and eateries in Woodstock’s quaint village.

Things to do recommended for groups

Groups visiting Woodstock can enjoy a scenic tour of the charming village, explore the picturesque Marsh-Billings-Rockefeller National Historical Park, and savor local flavors at the Woodstock Farmers' Market. Don't miss the chance to experience the vibrant art scene and cozy group dining options at local eateries.

*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 traveling with a group, family, or pets, or if you're planning an extended stay, 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 require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all 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.
  • Taking your pets with you to Woodstock: For many families, a trip isn’t truly fulfilled without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of vacation rentals that offer special rates 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 rental options. Don’t forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Woodstock

Woodstock, Vermont, offers an enchanting blend of adventure and history, making it an ideal vacation spot. Visitors can immerse themselves in family-friendly festivals, explore scenic views of the mountains, and enjoy the warmth of friendly locals. Nearby attractions like Oak Island and various excursions enhance the experience, ensuring a memorable stay filled with outdoor activities and captivating landscapes. Whether skiing in the winter or hiking in the summer, Woodstock promises a delightful escape.

  • Hanover: Located 13 miles from Woodstock, Hanover is a vibrant college town known for its rich cultural scene and outdoor adventures. Home to Dartmouth College, visitors can explore historic campus buildings and enjoy various educational events. The area offers numerous outdoor activities, including hiking and skiing in the nearby mountains. The picturesque Connecticut River provides opportunities for kayaking and scenic walks. Be sure to visit the local shops and eateries that reflect the town's charming New England character.
  • Quechee: Just 5 miles from Woodstock, Quechee is a haven for outdoor enthusiasts and adventure seekers. Famous for its breathtaking Quechee Gorge, the area offers stunning views and hiking trails that cater to all skill levels. The Quechee Ski Resort is a highlight for winter sports fans, featuring excellent skiing and snowboarding options. Additionally, the town is home to a delightful selection of shops, galleries, and restaurants, making it a great spot to unwind after a day of exploration.
  • South Woodstock: Located a mere 4 miles from Woodstock, South Woodstock is a quaint village that embodies the charm of rural Vermont. This area is perfect for those seeking ski adventures, with close access to several ski resorts and trails. The surrounding landscape is characterized by picturesque lakes and majestic mountains, offering ample opportunities for hiking, fishing, and photography. Don’t miss the iconic covered bridge, which adds a touch of historical charm to your visit.

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 next adventure? A little flexibility with your travel dates can go a long way, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your booking. It truly pays to be the planner. When you join our travel rewards program, One Key, you’ll gain immediate access to member savings and can earn and redeem OneKeyCash on qualifying reservations. Sign up today to start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume planning from where you last stopped, or organize your travel arrangements. You'll see your saved or booked properties neatly sorted into categories like Potential, Upcoming, or Current Trips. To get started with 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:

  • Union Arena Community Center (1.7 mi / 2.7 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:

  • 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)
  • 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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