Woodstock holiday lettings

We found 1,071 holiday rentals — enter your dates for availability

Discover a selection of 30 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:6 Mar - 13 Mar

Image gallery for All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!

Winter looking Southeast
9.8 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!

Mount Holly, VT

8% off
Price is £2,726
for 7 nights, 1 cabin
£389 per night
includes taxes & fees
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!

Find spaces that suit your style

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.

Popular types of accommodation in Woodstock

If you're pondering the ideal accommodation for your getaway to Woodstock, look no further. Our most sought-after options include houses, cosy cabins, and stylish condos, ensuring a perfect fit for every traveller's needs. With our extensive range of Woodstock holiday rentals, you’ll find the ideal house rental to make your stay both enjoyable and memorable. Discover the charm of vacation rentals in Woodstock today!

  • Houses: The top choice for visitors to Woodstock, offering spacious and comfortable accommodation ideal for families or groups.
  • Condos: A well-liked option, providing modern amenities and a convenient base for exploring the area.
  • Cabins: Perfect for those seeking a rustic experience surrounded by nature, these charming lodgings are a popular retreat.
  • Cottages: Quaint and inviting, cottages offer a delightful stay with a homely atmosphere.
  • Apartments: A practical choice for solo travellers or couples, offering flexibility and independence during your visit.**

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.

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.

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

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.

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)
  • 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)
  • Lakota Lake (7.7 mi / 12.4 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)

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, a popular area to stay is the picturesque village centre. This charming area is known for its classic New England aesthetic, featuring beautifully preserved historic architecture and a vibrant atmosphere. Staying here puts you in close proximity to top attractions such as the iconic Woodstock Inn and the tranquil grounds of Marsh-Billings-Rockefeller National Historical Park, where you can explore scenic trails and learn about the region's conservation history.

Another delightful option is to look for accommodations near the Ottauquechee River, which offers a serene backdrop and lovely views. This area is superb for those who enjoy outdoor activities, as it provides easy access to kayaking, fishing, and stunning walking paths along the river. In this vicinity, you might find a variety of properties ranging from quaint cottages to charming lodges, suiting different tastes and budgets.

For a more rural experience, consider staying in the surrounding countryside, which boasts stunning landscapes and a peaceful setting. This area offers a wealth of opportunities for hiking and enjoying the natural beauty of Vermont, while still being a short drive from the village centre and its attractions.
How much does it cost to rent a holiday home in Woodstock?
Prices for holiday 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 holiday 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 those seeking ski resort rentals in Woodstock, Vermont, the area surrounding the Killington Resort is highly recommended. Just a short drive away from Woodstock, Killington offers a wide array of accommodation options, including spacious chalets and cosy condos, superb for families or groups. Many of these properties come equipped with amenities such as fireplaces, hot tubs, and fully equipped kitchens, allowing guests to relax in comfort after a day on the slopes.

In Woodstock itself, visitors can find charming inns and bed-and-breakfasts that provide a more intimate experience. These often feature unique, individually decorated rooms with en-suite bathrooms, and some may include hearty breakfast options to fuel up for a day of skiing. The picturesque town also boasts local shops and restaurants, adding to the charm of the stay.
What is the most popular type of holiday rental accomodation in Woodstock?
In Woodstock, holiday houses are the most popular type of accommodation, with around 32 available in the area. These properties are typically situated in picturesque settings, offering a rustic charm that complements the town's New England vibe. Most holiday houses come with fully equipped kitchens, spacious living areas, and outdoor decks or porches—superb for enjoying the scenic views of the surrounding landscape.
Are there any family house rentals in Woodstock?
In Woodstock, Vermont, there is a robust selection of family-friendly house rentals, with around 37 options available. This charming town offers a picturesque setting superb for families, with properties often located near the scenic Ottauquechee River and the stunning landscapes of the Green Mountains. Many of these homes boast spacious living areas, well-equipped kitchens ideal for family meals, and outdoor spaces where children can play and explore.
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, providing an excellent option for those seeking relaxation and leisure during their stay. The area is known for its picturesque charm, with beautiful landscapes and a quaint village atmosphere. Many properties come equipped with amenities such as private pools, hot tubs, and outdoor spaces ideal for enjoying the stunning views, along with fully equipped kitchens for convenient meal preparation.
Can I find long-stay holiday rentals in Woodstock?
A long-stay holiday 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, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

The charming town of Woodstock, known for its picturesque scenery and vibrant community, offers easy access to pet-friendly points of interest. The nearby Marsh-Billings-Rockefeller National Historical Park is a fantastic spot for hiking with pets, featuring well-maintained trails that allow leashed dogs. Additionally, the town's scenic parks and trails provide ample opportunities for outdoor activities, making it a great destination for pet owners.
Are there any remote work holiday rentals in Woodstock?
In Woodstock, Vermont, there is a substantial selection of remote work holiday rentals, with around 39 properties available to cater to your needs. This picturesque town, known for its charming New England scenery and vibrant arts scene, offers various accommodations that are well-suited for remote work. Many of these properties feature dedicated workspaces, including desks and comfortable office chairs, ensuring a productive environment. High-speed Wi-Fi is commonly provided, along with additional amenities such as computer monitors to enhance your work setup. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woodstock holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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.
How early should I book a Woodstock holiday rental?
Book your Woodstock holiday 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 holiday 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 take part in a charming New England atmosphere with a variety of attractions. The picturesque village centre features the iconic Woodstock Inn, a great spot for dining and relaxation, and is often surrounded by quaint shops and art galleries showcasing local craftsmanship. Just a short stroll away, the Marsh-Billings-Rockefeller National Historical Park offers beautiful trails and a glimpse into the area's conservation history.
Can I change or cancel my Woodstock home rental booking on Vrbo?
To find Woodstock holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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