Woodstock holiday rentals

We found 1,090 holiday rentals — enter your dates for availability
Discover a selection of 33 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:30 Oct - 6 Nov

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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 home?
If you're thinking of a getaway to Woodstock, West Woodstock is one of the most desirable neighbourhoods to stay. Whether you're looking for a cottage, condo or another property type, you'll always have the entire place to yourself.
What is the most popular type of holiday home accommodation in Woodstock?
Based on our data, houses are the most in-demand holiday property type in Woodstock. But of course, everyone's idea of an awesome trip can vary. Stayz has holiday homes of all sizes and shapes, and we'll help you locate the perfect fit.
How much does it cost to rent a holiday home in Woodstock?
Different things can affect the price of a holiday home in Woodstock, such as the time of year, property type and length of stay. Still, all Stayz homes have something in common — unbeatable value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Woodstock?
When you travel and the style and size of the property will influence the cost of your beachside escape. Type in your Woodstock travel dates to view your available options on Stayz. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday homes in Woodstock?
Pack a tug toy and treats for the pooch in your life because Woodstock has 13 stays that roll out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Woodstock?
Add another level of fun to your adventure by booking one of the three houses with a private pool in Woodstock. Use our search filter to find the kind of property you want on Stayz, and then spend leisurely days playing and splashing in a swimming pool that's for your exclusive use.
What are popular home amenities in Woodstock?
When it comes to home amenities that people are looking for in Woodstock, mountain views, a garden and a water view rank highest. With Stayz holiday homes, there are choices to match your style and taste, whether you're going on a trip with your partner, your family or even pets.
Are there large group holiday homes in Woodstock?
Take your pick of seven Stayz holiday properties in Woodstock that can sleep five or more people. You'll get all the privacy and space you need to hang out with your loved ones — and nobody else.
Are there holiday homes in Woodstock that welcome kids?
Woodstock has 13 family-friendly holiday homes to pick from. And finding a stay that welcomes children is a breeze with Stayz's "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get conveniences and perks such as bunk beds, private pools and yards.
What are the top attractions for families in Woodstock?
There are plenty of awesome things to do and see with the family in Woodstock, such as:

  • Mount Tom Peak
  • Lakota Lake
  • Union Arena Community Centre

Are there one-bedroom holiday homes in Woodstock?
You can choose from four one-bedroom homes in Woodstock. Whether you're searching for a comfy cottage or a cabin, Stayz's one-bedroom homes are great if you don't need huge amounts of space. One of the main perks of having your own pad? You'll never need to share your trip with strangers.
Are there holiday homes with WiFi in Woodstock?
Take your pick of five holiday homes with WiFi in Woodstock. If you want to disconnect from the world during your break, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Woodstock?
Woodstock has seven holiday homes where you can relax and recharge in air-conditioned comfort. To locate a property on Stayz that offers this perk, choose your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Woodstock?
Age restrictions can differ between properties on Stayz, so check the rules of the holiday home in Woodstock you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Woodstock for?
The amount of time you can book a Woodstock holiday home for is down to the property. Just enter your dates of travel to view options that offer extended stays. They feature everything you need to make your extended trip more enjoyable and comfortable, such as kitchens and laundries. Some Stayz holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.