Woodstock holiday rentals

We found 1,089 holiday rentals — enter your dates for availability
Discover a selection of 34 homes and other holiday rentals in Woodstock that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as air conditioning and a pool. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Woodstock

Showing deals for:20 Nov - 27 Nov

Image gallery for Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!

Welcome to the Highline Lodge!
10 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)

Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!

Killington

8% off
Price is AU$23,107
for 7 nights, 1 room
AU$3,301 per night
includes taxes & fees
Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!

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Why visit Woodstock

  • Historic charm: Woodstock captivates with its well-preserved historical houses and landmarks, offering a glimpse into New England’s rich past.
  • Scenic outdoors: Enjoy hiking and skiing amidst picturesque landscapes and natural state park settings, ideal for adventure seekers.
  • Cultural immersion: The town’s vibrant local scene and heritage invite visitors to explore its unique character.
  • Family-friendly fun: Woodstock provides a range of activities perfect for family outings and leisurely explorations.
  • Welcoming atmosphere: Experience the warm, inviting spirit of Woodstock, making every visit memorable.

Popular types of accommodation in Woodstock

Discover Woodstock, Vermont, a charming destination offering an array of accommodation options including private holiday homes, cosy condos, and rustic cabins. Enjoy the best Woodstock accommodation with delightful breakfasts, local attractions, and star accommodations that provide transparency and savings. Explore this picturesque town known for its welcoming atmosphere and memorable experiences.

  • Private Holiday Homes: The top choice for visitors seeking a home-like atmosphere, offering comfort and privacy for families or groups.
  • Condos: A popular option featuring modern amenities and often situated in convenient locations for easy access to local attractions.
  • Cabins: Ideal for those wanting a rustic experience, nestled in nature, perfect for a peaceful retreat.
  • Apartments: A practical alternative for solo travellers or couples, providing essential comforts in a compact space.
  • Cottages: Charming and quaint, these cosy retreats offer a delightful blend of character and comfort.**

Top attractions in and around Woodstock

Woodstock, Vermont, offers a blend of cultural heritage and outdoor adventures, from historic houses and scenic canyons to family-friendly activities. Visitors can explore the rich history of the area and enjoy a variety of experiences, including skiing and hiking in the national state park settings. The charming town provides an inviting atmosphere for those seeking both relaxation and active pursuits, making it a perfect destination for a memorable holiday.

  • Quechee Gorge Bridge: This stunning canyon offers breathtaking views and outdoor adventures. Walk along the bridge for picturesque scenery and opportunities for hiking and photography amidst the dramatic cliffs.
  • Marsh-Billings-Rockefeller National Historical Park: A cultural gem in Woodstock, this park showcases the region's remarkable history, with beautiful gardens and trails that invite exploration of its rich heritage and conservation efforts.
  • Mount Tom Peak: A popular destination for outdoor enthusiasts, this peak provides invigorating hiking trails and panoramic vistas of the surrounding landscape, perfect for adventure seekers and nature lovers alike.

Things to do recommended for couples

Discover the charm of Woodstock, Vermont, perfect for couples seeking a romantic retreat. Enjoy leisurely walks through quaint streets, savour local cuisine, and immerse yourselves in the idyllic countryside.

Things to do recommended for families

Families will delight in visiting historic covered bridges, exploring quaint village shops, and enjoying scenic walks along the Ottauquechee River, offering a truly local experience in Woodstock, Vermont.

Things to do recommended for groups

Discover local charm in Woodstock, Vermont with group-friendly activities such as exploring historic villages, enjoying artisan food tours, and partaking in scenic hikes through rural landscapes. Experience authentic New England culture and create lasting memories with your mates.

*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

If you're travelling with a group, family, pets, or seeking extended stays, it's important to filter your options according to your key priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas suitable for group gatherings. Thankfully, you can apply filters for all of these options and more on Stayz.
  • Traveling to Woodstock with young kids: Travelling with young children can present its own set of challenges. It’s essential to prioritise their comfort and safety, along with ensuring access to suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many, a family holiday wouldn’t be the same without their four-legged companion by their side. If that resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Woodstock: If you’re seeking holiday 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 consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay near Woodstock

Woodstock, Vermont, offers a charming blend of history and outdoor adventure, making it a perfect holiday destination. Visitors can explore scenic landscapes, partake in thrilling skiing activities, and enjoy the warm, welcoming atmosphere of this picturesque city. With its historical landmarks and family-friendly excursions, Woodstock invites travellers to immerse themselves in its unique vibe, ensuring an unforgettable experience in the heart of New England.

  • Hanover: Hanover is a vibrant city located 21km from Woodstock, offering a rich cultural tapestry and an array of outdoor and adventure experiences. Visitors can immerse themselves in the local educational scene by exploring the historic college university, or enjoy the nearby lake and mountain landscapes. The city is well-known for its ski field and ski activities, ensuring plenty of opportunities for winter sports enthusiasts and nature lovers alike.
  • Quechee: Quechee, just 8km from Woodstock, is renowned for its adventurous spirit and outdoor charm. This city invites visitors to engage in thrilling ski activities at the dedicated ski field and resort, while also offering opportunities to explore the scenic beauty of a lake and the dramatic canyon gorge. The presence of a historic college university adds a cultural dimension to the adventure, making Quechee a well-rounded destination for travellers.
  • White River Junction: Located 16km from Woodstock, White River Junction is celebrated for its blend of adventure and outdoor pursuits, particularly its well-established ski facilities. Travellers can enjoy skiing at local ski fields and resorts, while the nearby historic college university and natural features such as a lake and canyon gorge provide diverse attractions. This city is an ideal base for those seeking both cultural insights and exhilarating winter sports.

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 Stayz is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, opting for a longer stay frequently results in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's cutting-edge Trip Board offers you a convenient space to plan new trips, resume your previous arrangements, or view and organise your travel plans. You can easily access properties you’ve saved and booked previously within the Potential, Upcoming, or Current Trips sections. To make the most of Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The historical city of Woodstock awaits you

Enjoy the area's architecture, history and museums with a rental holiday home 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 holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Woodstock

Do you want to discover top things to see and do in the area? Venture out of your holiday home and experience everything that makes Woodstock a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 adventurous traveller or just want to take in the scenery, Woodstock is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • 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 centre. If you're unable to find a flight that fits your schedule, you could also fly into 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 holiday rental?
When considering a holiday rental in Woodstock, Vermont, the area surrounding the village itself is an excellent choice. This charming and picturesque neighbourhood offers a delightful blend of natural beauty and quaint New England charm. Staying here allows you to easily explore the local attractions, such as the iconic Woodstock Inn & Resort, which features beautiful grounds and a renowned spa. Another highlight is the Billings Farm and Museum, where visitors can immerse themselves in the region's agricultural history and enjoy interactive exhibits.

In terms of accommodation, Woodstock features a variety of properties, ranging from cosy cottages to elegant inns, providing a superb spot for both families and couples seeking a relaxing getaway. The village atmosphere, coupled with nearby walking trails and the stunning scenery of the Green Mountains, makes this area not only appealing but also convenient for enjoying all that Woodstock has to offer.
Where are the best Woodstock ski resort rentals?
For the best ski resort rentals in Woodstock, Vermont, visitors should consider properties located near the Killington Resort, which is just a short drive away. The picturesque village of Woodstock itself offers a range of charming accommodations, from rustic cabins to elegant inns. Many of these properties come equipped with amenities such as fireplaces, fully stocked kitchens, and outdoor spaces superb for enjoying the scenic views of the surrounding Green Mountains.

In the heart of Woodstock, you can find cosy lodges that provide easy access to both the ski slopes and local attractions like the Billings Farm & Museum and the picturesque Woodstock Green. These lodges often feature amenities like hot tubs, ski storage, and on-site dining options, enhancing the overall experience for guests.

For a more secluded experience, the nearby Pomfret area offers beautiful countryside homes that provide a tranquil retreat after a day on the slopes. Many of these rentals include spacious living areas, fire pits for evening gatherings, and proximity to hiking trails for those looking to explore the winter landscape.
What is the most popular type of holiday rental accomodation in Woodstock?
In Woodstock, holiday houses are the most popular type of holiday rental, with about 112 available in the area. These properties are often situated in picturesque locations, providing guests with stunning views of the surrounding landscape. Most holiday houses come equipped with fully functional kitchens, spacious living areas, and outdoor spaces such as decks or patios, making them ideal for families or groups looking to enjoy a cozy feel.

Additionally, there are around 20 apartments scattered throughout the town, offering a more compact and convenient option for those who prefer a smaller space. These apartments typically include essential amenities like kitchens and comfortable seating areas. For those seeking a rustic experience, several cabins, chalets, and cottages are also available, often featuring unique charm and close proximity to nature, great for a cozy retreat.
Are there any family house rentals in Woodstock?
In Woodstock, Vermont, there are numerous family-friendly house rentals available—around 31 options throughout the area. This picturesque town is known for its charming New England atmosphere, making it an excellent choice for families seeking both relaxation and adventure. Many of the properties feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.

Visitors can explore nearby attractions such as the Billings Farm and Museum, which offers a glimpse into the region's agricultural heritage, or take leisurely strolls along the scenic Ottauquechee River. The area is also close to the Green Mountain National Forest, providing ample opportunities for outdoor activities such as hiking, biking, and, in winter, skiing.
Can I rent a holiday home with a pool or hot tub in Woodstock?
In Woodstock, Vermont, there are several holiday homes available for rent that feature pools and hot tubs, making it an attractive destination for travellers seeking relaxation and leisure. The area is known for its picturesque landscapes, charming village centre, and outdoor activities, particularly in the warmer months.

Many of the available rentals come with amenities such as private pools, hot tubs, and expansive outdoor spaces, superb for family gatherings or a peaceful retreat. Inside, you can expect well-appointed kitchens for self-catering, comfortable living areas, and often fireplaces for those cooler evenings. The local scenery is breathtaking, with opportunities for hiking, cycling, and exploring the nearby Green Mountain National Forest, enhancing your stay in this idyllic setting.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, Vermont, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. Many of these holiday homes feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.

The picturesque town is surrounded by beautiful landscapes and outdoor activities, with nearby parks and trails that are superb for enjoying time with your furry friends. The Marsh-Billings-Rockefeller National Historical Park offers lovely walking paths and scenic views, while the Ottauquechee River provides opportunities for leisurely strolls alongside the water.

In the heart of Woodstock, you'll find charming shops and restaurants that often accommodate pets, enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Woodstock?
In Woodstock, Vermont, there is a substantial selection of remote work holiday rentals, with around 152 options available. This charming town is not only known for its picturesque scenery but also offers an array of amenities that cater to remote workers. Many properties come equipped with high-speed Wi-Fi, ensuring a reliable internet connection for work-related tasks. Some accommodations even have dedicated workspaces, such as desks or bookable units with printers, making it convenient for those needing to balance work and leisure.

The area is surrounded by natural beauty, with easy access to hiking trails and stunning views, providing a great backdrop for breaks during the workday. Additionally, the town features a delightful range of local shops and restaurants, allowing for a taste of the local culture. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Woodstock?
In Woodstock, popular rental amenities typically include kitchens, allowing guests to prepare their own meals with ease. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoyment of the picturesque surroundings. Onsite parking is commonly available, which is particularly beneficial for those travelling by car. Additionally, many rentals come equipped with coffee and tea makers, superb for enjoying a warm beverage while taking in the morning views. A fireplace is another sought-after feature, adding a cosy touch, especially during the colder months.
When is the best time to visit Woodstock for a holiday rental?
September is the most popular time to visit Woodstock, Vermont, as the autumn leaves begin to transform the landscape into a vibrant tapestry of colours. This period falls within the peak season, which spans from August to October, attracting visitors eager to immerse themselves in the stunning natural beauty and outdoor activities the area has to offer.

During these months, the weather is typically mild, with temperatures ranging from around 10 to 20 degrees Celsius, making it great for hiking, exploring local shops, and strolling through the charming streets of this quintessential New England town. Outdoor enthusiasts can take advantage of the scenic trails and picturesque parks, with plenty of opportunities for leisurely sightseeing and enjoying the crisp fall air.

For those looking for a more budget-friendly option, consider visiting in March. While this month is on the quieter side, it offers a great experience with fewer crowds. It's a great time for those who appreciate a more peaceful atmosphere, as you can still enjoy the beauty of the winter landscape with potential opportunities for early spring activities as the snow begins to melt.
What are the top attractions in Woodstock?
In Woodstock, Vermont, visitors can enjoy a variety of attractions that showcase the area's natural beauty and charming New England architecture. The picturesque Woodstock Village is a highlight, featuring historic buildings, boutique shops, and delightful eateries that capture the town's quaint charm. The nearby Marsh-Billings-Rockefeller National Historical Park offers miles of scenic trails great for hiking and exploring the region's lush landscapes.

Another must-visit is the Billings Farm & Museum, where guests can learn about Vermont's agricultural heritage and interact with farm animals. The stunning Quechee Gorge, just a short drive away, provides breathtaking views and opportunities for outdoor activities like hiking and picnicking. Additionally, the area is known for its covered bridges, such as the Middle Bridge, which are iconic sights and great for photography enthusiasts.

For those interested in culture, the Norman Williams Public Library and the Woodstock History Centre offer insights into the local history and community events throughout the year.
Are all fees included in the Woodstock holiday homes prices shown on Stayz?
Stayz 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.
Are there any Woodstock holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Woodstock holiday homes?
You can find great discounts on holiday homes in Woodstock on Stayz, 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.
Can I change or cancel my Woodstock holiday home booking on Stayz?
To find Woodstock holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Woodstock?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Woodstock holiday home?
Book your Woodstock holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Woodstock?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Woodstock to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.