Woodstock holiday lettings

We found 1,078 holiday rentals — enter your dates for availability

Discover a selection of 37 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:17 Oct - 24 Oct

Why visit Woodstock

  • Outdoor Adventures: Woodstock offers excellent opportunities for skiing and various outdoor activities amidst stunning natural scenery.
  • Rich History: Explore charming historic houses and visit nearby historic colleges that showcase the area’s fascinating past.
  • Family-Friendly Experiences: The town is perfect for families, offering engaging activities suitable for all ages.
  • Charming Atmosphere: Enjoy the friendly vibe of Woodstock, complemented by scenic surroundings and welcoming locals.
  • Diverse Accommodation: Choose from private vacation homes, cosy cabins, and stylish condos for a memorable stay.

Top attractions in and around Woodstock

Woodstock, Vermont, is an ideal destination for those seeking adventure and outdoor activities, with excellent opportunities for skiing. The area boasts a variety of attractions, including historic colleges, national parks, and charming historic houses. Visitors can immerse themselves in the local culture while enjoying family-friendly experiences amidst the stunning natural scenery. Whether you're travelling solo or with loved ones, Woodstock offers a delightful blend of history and outdoor exploration.

  • Quechee Gorge Bridge: A stunning natural marvel, the Quechee Gorge Bridge offers breathtaking views of the deep gorge below. It’s perfect for outdoor enthusiasts seeking adventure, with trails for hiking and photography, showcasing the area's rugged beauty.
  • Dartmouth College: This prestigious institution boasts beautiful architecture and a rich history, providing a cultural experience steeped in academic tradition. Stroll through its scenic campus to appreciate art, history, and vibrant student life.
  • Billings Farm and Museum: A living museum that celebrates Vermont's rural heritage. Visitors can engage with farm animals, explore historic buildings, and learn about sustainable agriculture, making it a delightful experience for all ages.

Things to do recommended for couples

For a romantic getaway in Woodstock, indulge in skiing at Saskadena Six Ski Area, rejuvenate together at The Strong House Spa, and savour delightful treats at the renowned King Arthur Baking Company nearby. Each experience promises to create cherished memories for you both.

Things to do recommended for families

Families can have a splashing good time at the Upper Valley Aquatic Center, located 5.6km from Woodstock. Enjoy ice skating at the Union Arena Community Center, right in town, or unwind at Wilderness Trails, just 3.7km away, offering a serene recreational experience.

Things to do recommended for groups

Explore the scenic beauty of Quechee Gorge Village, just 3.7km from Woodstock, or enjoy a captivating performance at the Woodstock Town Hall Theatre, where culture and romance intertwine. For a bit of sport, head to the Woodstock Country Club for a delightful round of golf amidst stunning outdoor vistas.

Booking with Vrbo is a breeze

Are you hoping to save money on your next holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We’re here to help you find the perfect stay.

Where to stay near Woodstock

Woodstock, Vermont, offers a delightful blend of adventure and history, making it an ideal getaway for families. Explore the charming streets and scenic surroundings, perfect for outdoor activities and excursions. Nearby regions, including Fort Worth and New Hampshire, provide a friendly atmosphere that enhances your experience. Whether you’re skiing on the slopes or enjoying the picturesque scenery, Woodstock promises a memorable holiday filled with friendly people and captivating vibes.

  • Quechee: Quechee, located a mere 3.1km from Woodstock, is a haven for adventure seekers and outdoor enthusiasts. Known for its stunning natural beauty, visitors are drawn to the Quechee Gorge, where breathtaking views and hiking trails abound. The area is also popular for skiing, with excellent ski fields and resorts that cater to both beginners and experienced skiers. In addition to winter sports, the picturesque lake offers opportunities for fishing and kayaking, making it an all-season destination.
  • White River Junction: Situated 6.2km from Woodstock, White River Junction is a vibrant city brimming with adventure and culture. This area is particularly renowned for its skiing facilities, making it a hotspot for thrill-seekers during the winter months. The historic college and university nearby provide a cultural touch, with galleries and performances enriching the local scene. Visitors can explore the nearby canyon gorge and iconic bridges, adding a touch of natural beauty to their travel experience.
  • Hanover: Approximately 8.1km from Woodstock, Hanover is celebrated for its cultural vibrancy and outdoor adventures. Home to a prestigious university, the city offers a plethora of educational experiences alongside its scenic surroundings. Outdoor enthusiasts can indulge in skiing or enjoy the tranquil lakes and mountains nearby. The blend of academia and nature makes Hanover a unique destination, inviting visitors to explore its historic sites, picturesque landscapes, and lively community events.

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

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

If you're travelling with a group, family, pets, or planning for an extended stay, it's essential to filter your search according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas 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 be quite demanding. It’s essential to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is advisable.
  • Taking your pets with you to Woodstock: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and 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 place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board provides you with a dedicated space to plan new holidays, pick up from where you last left off, or to view and organise your travel arrangements. You can easily find any properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/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 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)
  • Left Bank Books (12.7 mi / 20.4 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?
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 rental 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. Vrbo has holiday rentals of all sizes and shapes, and we'll help you locate the perfect fit.
How much does it cost to rent a holiday rental in Woodstock?
Different things can affect the price of a holiday rental in Woodstock, such as the time of year, property type and length of stay. Still, all Vrbo 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 Vrbo. 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 rentals 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 rentals on Vrbo. 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 Vrbo, and then spend leisurely days playing and splashing in a swimming pool that's for your exclusive use.
What are popular rental amenities in Woodstock?
When it comes to rental amenities that people are looking for in Woodstock, mountain views, a garden and a water view rank highest. With Vrbo holiday rentals, 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 rentals in Woodstock?
Take your pick of seven Vrbo 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 rentals in Woodstock that welcome kids?
Woodstock has 13 family-friendly holiday rentals to pick from. And finding a stay that welcomes children is a breeze with Vrbo'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 rentals in Woodstock?
You can choose from four one-bedroom rentals in Woodstock. Whether you're searching for a comfy cottage or a cabin, Vrbo's one-bedroom rentals 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 rentals with WiFi in Woodstock?
Take your pick of five holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Woodstock?
Woodstock has seven holiday rentals where you can relax and recharge in air-conditioned comfort. To locate a property on Vrbo 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 rental in Woodstock?
Age restrictions can differ between properties on Vrbo, so check the rules of the holiday rental in Woodstock you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday rental in Woodstock for?
The amount of time you can book a Woodstock holiday rental 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 Vrbo holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.

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