Find Vacation Rentals in Woodstock (VT)

Highlights Woodstock (VT)

  • Vacation rentals
  • Exciting getaway
  • Interesting outdoor activities
  • Historical and Cultural Activities

Best Vacation Rentals in Woodstock (VT)

Guests agree: these stays are highly rated for location, cleanliness, and more.
Woodstock (vt), Windsor County
Vacation Rental • 2992 ft² • 4 Bedrooms
(10 reviews)
Woodstock is a beautifully preserved traditional New England village with year round outdoor activities on offer. From the end of the Village Green, it's a short walk uphill to the house set on nearly 12 acres. Renovated inside and out in 2009, the house is perfect for up to six people (in accordance with Woodstock Village rental occupancy rules) with a chef's kitchen and a generous comfortable sitting room with wood burning fireplace. French doors open to a stone terrace offering outdoor dining and spectacular sunset views. Wood floors throughout and rooms filled with natural light.Upstair...
from $953 / night
Woodstock (vt), Windsor County
Vacation Rental • 8 Guests • 8 Bedrooms
Modern 3 bedroom, 2 bath house with beautiful views and total privacy. In floor radiant heat, expansive southwest facing windows, gourmet kitchen. Upstairs master bedroom has Queen bed and en suite bath. Two ground floor bedrooms each have two twin beds and shared bath. Separate laundry/utility room. Common first floor spaces consist of two 400 square foot pavilions with vaulted ceilings, one for kitchen/dining and one for living room. In floor radiant heat throughout, glass door wood stove in living room. Large front deck for outdoor dining. Property is situated on five acres which backs u...
from $351 / night
Woodstock (vt), Windsor County
Vacation Rental • 1496 ft² • 4 Bedrooms
(68 reviews)
Sunny 4 bedroom 2 bath home sleeps 7 in beds. Located on 4 lush acres of rolling fields, mature trees and streams, this single level custom built ranch house is conveniently located near everything, yet is private with spacious lawns and not a neighbor in sight ! Only 3 miles from historic Woodstock Village, which offers small town fine shopping and a variety of quality restaurants as well as fun for the kids at Billings Farm and golf at the famous Woodstock Country Club. Woodstock offers many year-round activities, including skiing at Saskadena (formerly known as Suicide 6) in Pomfret (6 m...
from $378 / night

Prices and availability

Current Vacation rental prices Woodstock (VT)

$451for 3 Jun - 10 Jun
$408 annual average
Average price per week

Current vacation rental availability Woodstock (VT)

25%for 3 Jun - 10 Jun
36% annual average
Percentage of available rentals

Vacation rentals in Woodstock (VT)

Vacation rentals accommodations

Are you in for a perfect holiday rental experience? Then, Woodstock (VT) is the place. Whether you want to reconnect with nature or be pampered in a luxurious resort, the area has much to offer visitors. From cozy cabins to sprawling estates, vacation rental homes in Woodstock (VT) provide plenty of space and privacy for groups of all sizes. Most vacation rental properties are located within a few minutes' drive of the town center, making it easy to explore all that Woodstock (VT) has to offer. In addition, the area's natural scenery and rural charm provide a perfect backdrop for a relaxing getaway. The rental properties are also pocket-friendly. They vary considerably in size and amenities, so visitors can choose one that meets their specific holiday needs. For those looking to spend some quiet time fishing or bird watching, there are plenty of secluded homes surrounded by nature. Woodstock (VT) is the shire town of Windsor County and is famous for its charming New England villages and vibrant arts scene. The Woodstock (VT) Art Festival is held every September and attracts visitors worldwide.

Warm-hearted vacation rentals for everyone

The rental properties in Woodstock (VT) are full of warmth and rich in history. Comfortable beds, spacious rooms, and easy-to-use appliances will help you feel right at home while on vacation. You'll be able to relax in the heart of Vermont's natural beauty, surrounded by interesting towns, delicious restaurants, and popular attractions. Whether you plan to travel with your family, friends, significant other, or pet, there are vacation rentals in Woodstock (VT) that will suit your needs. The playgrounds are endless, and the scenery is relaxing. There is no room for boredom as most rental homes have internet, TVs, and fireplaces. The kitchen, living rooms, and bedrooms have the amenities like dishwashers, washers and dryers, microwaves, ovens, and refrigerators that you are used to at home. In addition, you can find some houses with garages, front-entry, or side-entry at the property. It is a cool feeling to pull right up to your vacation rental and not have to worry about luggage or parking.

Vacations in Woodstock (VT)

The area and getting around

Attractive neighborhoods

An attractive neighborhood is one of the top priorities for many people when choosing a place to live. There are many lovely neighborhoods in Woodstock, Vermont, to choose a vacation rental. Mountains such as Overlook Mountain and Buck Hill can be seen from some neighborhoods. The town is also close to the Green Mountain National Forest, perfect for camping and hiking. The Ottauquechee River flows through the town and is a popular spot for fishing, kayaking, and tubing. There are also several small lakes, perfect for swimming and boating. In addition, Woodstock is close to several ski resorts in the winter, including Killington, Okemo, and Stratton. Museums such as the Woodstock Historical Society are also worth visiting if you want to learn more about the town's history.

Amazing area to stay

You are in the perfect place when you are within Woodstock (VT) for your holidays. The town of Woodstock covers a small area but has so much to offer. The authorities here never gamble with your security issues. The rentals are manned, and you are given access to the best safety measures. The roads are well maintained, so if you want to get the nature of Vermont in all its glory, a car is the best way to go. The restaurants here are also amazing, and they offer a variety that caters to all, whether you are looking for a five-star restaurant or something a little more homely. The people here are also very friendly and always up for a chat. You will never find yourself bored in this town, which is for sure. Woodstock will not disappoint if you are a live music fanatic or movie enthusiast. You can find various venues that offer these events, and they always have something new to offer.

Travelers and activities

Woodstock (VT) for sport and nature lovers

If you are sports and nature lovers, a Woodstock (VT) holiday can fulfill all your desires. The availability of the Ottauquechee River and the numerous mountain biking and hiking trails make the town a paradise for those who love outdoor activities. In addition, Woodstock (VT) is home to the Billings Farm & Museum, the Quechee Gorge, and the Suicide Six Ski Area. These museums and attractions can be enjoyed by riding a motorbike or driving around the town. The historic and picturesque town is also an attraction in its own right. The buildings, churches, and other features date back to the 18th century, and the town was even used as a filming location for the Woodstock (film).

Woodstock (VT) for culture and history enthusiasts

The culture and history of Woodstock (VT) would easily interest everyone of all ages. Several museums and art galleries in Woodstock (VT) make this town a must-visit place for those who have a keen interest in culture and history. In addition, many interesting shops, restaurants, and cafes can be found in the downtown area selling traditional foods and items.

Woodstock (VT) is one of the most popular tourist destinations in the state of Vermont. Sport and nature lovers are always looking for new adventures and attractions to explore, while culture and history enthusiasts can spend hours browsing through the many interesting shops and museums.

Top 5 travel tips in Woodstock (VT)

1. Billings Farm & Museum

The Museum is perfect for all ages. They have many different animals, including cows, pigs, goats, horses, and chickens. The place is enjoyable for children and adults.

2. Ottauquechee River

The river provides swimming, fishing, and kayaking. If you want to relax, this is the perfect place for you. You can visit around Memorial Day or Labor Day if you want to go tubing or swimming.

3. Green Mountain National Forest

Green Mountain National Forest is a great place for hiking and biking. There are also many different lakes that you can visit.

4. The Town Hall Theater

If you are a movie lover, the Town Hall Theater is the perfect place for you. They have a wide variety of movies, and it's very affordable.

5. The Woodstock Inn

The inn is a great place to stay if you want to be close to all the action. The staff is very friendly, and they have many amenities to offer, such as a spa and a restaurant.

FAQs: Vacation Rentals in Woodstock (VT)

How much does it cost to book a vacation rental in Woodstock?

At an average cost of $447 per night, Woodstock lies at the upper end of the price range for vacation rentals in the USA.

What time of year offers, on average, the best vacation rental prices in Woodstock?

]If you are looking to get the most out of your money, the most budget-friendly months to visit Woodstock are September ($331 the average per night for accommodation), May ($336), and August ($372).

During which months are vacation rentals more expensive in Woodstock?

When it comes to looking for a vacation rental in Woodstock, the months that cost the most are, in order of highest to lowest, October, February and November, with average prices per night of $618, $602, and $602, respectively.

Are there usually many vacation rentals available in Woodstock?

If you decide to put Woodstock on your bucket list, we suggest planning your vacation long before you go because it tends to be very high in demand, with an annual average of 91% of rentals booked the previous year.

What are the best months for a spontaneous getaway?

Last year, the months with more available accommodation of the year in Woodstock were April, November and October, with average availabilities of 34%, 22%, and 14%, respectively.

How many vacation rentals are there in Woodstock?

We have 30 properties for you in Woodstock, provided by our 2 local and international partners.

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