Photo by Marina Timo

Woodstock vacation rentals

We found 717 vacation rentals — enter your dates for availability

Discover a selection of 65 homes, 12 apartments, and other vacation rentals in Woodstock that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Find out more about Woodstock

Find out more about Woodstock

Why visit Woodstock

  1. Scenic Outdoor Adventures: Experience hiking and exploring nature preserves in the lush surroundings of Woodstock.
  2. Vibrant Artistic Community: Immerse yourself in the local art scene, featuring galleries and cultural events.
  3. Historic Charm: Discover the town's rich history through its charming architecture and nearby historic colleges.
  4. Welcoming Locals: Enjoy the warm hospitality of friendly residents who enhance your vacation experience.
  5. Diverse Accommodations: Choose from cozy cottages, charming cabins, and private vacation homes for a perfect stay.

Popular types of accommodation in Woodstock

Planning a getaway to Woodstock? The excitement begins with selecting the perfect place to stay! Explore a variety of popular accommodations, including houses, charming cabins, and quaint cottages. Whether you're looking for spacious Vaughan vacation rentals or a cosy bedroom townhouse, our platform ensures you find the ideal spot for your holiday. Enjoy transparency and savings as you make unforgettable memories in this beautiful destination.

  • Houses: The top choice for visitors to Woodstock, offering spacious accommodations ideal for families, friends, or couples seeking comfort and privacy.
  • Cabins: A close second, these rustic retreats provide a peaceful escape surrounded by nature, perfect for outdoor enthusiasts.
  • Cottages: Charming and intimate, cottages are a delightful option for those looking for a cozy getaway.
  • Apartments: Convenient and versatile, apartments offer a modern living experience in the heart of Woodstock.
  • Chalets: These unique lodgings combine rustic charm with modern amenities, ideal for a memorable stay.**

Top attractions in Woodstock

Woodstock, New York, offers a perfect blend of outdoor adventure and scenic beauty, making it an ideal vacation spot. Visitors can explore various attractions such as nature preserves, historic colleges and universities, and stunning waterfalls. Whether you're seeking cultural experiences, family-friendly activities, or simply a chance to immerse yourself in nature, Woodstock provides plenty of opportunities to enjoy the great outdoors and create lasting memories.

  1. Bethel Woods Museum: Located 4.8km from Woodstock, this museum celebrates the cultural legacy of the 1969 Woodstock Festival. Explore engaging exhibits that highlight music, art, and peace movements, all set in a picturesque landscape.
  2. Bard College: Situated 17.7km away, Bard College is a historic institution known for its stunning architecture and vibrant arts scene. Stroll through its scenic campus and enjoy performances or exhibitions that showcase diverse cultural expressions.
  3. Kaaterskill Falls: About 17.7km from Woodstock, this majestic waterfall offers a romantic and adventurous experience. Hike the trails for breathtaking views and immerse yourself in the beauty of nature.

Things to do recommended for couples

Looking for a romantic getaway in Woodstock? Explore the adventure of skiing at Hunter Mountain or take a scenic ride on the H Ski Lift. For a relaxing experience, indulge in rejuvenating treatments at Copperhood Retreat & Spa, perfect for unwinding together.

Things to do recommended for families

Families can unwind at Saugerties Village Beach, just 14.5km from Woodstock, enjoying its wellness vibe. For adventure, head to Kiwanis Ice Arena for ice skating, or catch a game at Dietz Stadium, both also 14.5km away, offering a lively sports atmosphere.

Things to do recommended for groups

Groups visiting Woodstock, New York can hike the scenic Overlook Mountain Trailhead, shop for unique finds at the Woodstock Music Shop, and enjoy a round of golf at the Woodstock Golf Club, all while soaking in the area's vibrant outdoor atmosphere.

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

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, it's important to apply the right filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with seeking out suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Woodstock: For many families, a trip wouldn't feel complete without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Woodstock: If you’re in search of vacation rentals that offer discounts 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 rental options. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Woodstock

Woodstock, New York offers a delightful blend of outdoor adventures and artistic vibes, perfect for family vacations. Explore scenic locations and quaint towns nearby, where friendly locals welcome you with open arms. Whether you're hiking in the lush surroundings or enjoying the vibrant art scene, you'll find a relaxing atmosphere ideal for creating lasting memories. Don't miss the opportunity to unwind in this charming town that beautifully captures the essence of adventure and serenity.

  • Kingston: Located approximately 16.1km from Woodstock, Kingston is a vibrant city that beautifully combines outdoor adventure with rich history. With its scenic mountain views and tranquil lakes, travelers can indulge in a variety of outdoor activities, from skiing at local resorts to exploring historic landmarks, including a renowned college. Kingston’s charming downtown area offers unique shops, restaurants, and cultural experiences, making it a delightful stop for both outdoor enthusiasts and history buffs.
  • Saugerties: Just 14.5km from Woodstock, Saugerties is a picturesque city known for its stunning natural landscapes and outdoor recreation. The area is perfect for skiing, with easy access to several ski fields and resorts. Beyond winter sports, visitors can explore the beautiful mountains and lakes that surround the city. Saugerties also boasts a lively atmosphere with local shops, eateries, and scenic spots, including a historic stadium that adds to its charm, making it an ideal destination for adventure seekers.
  • Zena: Nestled within the Woodstock area, Zena is a quaint village that offers an immersive outdoor experience. Known for its breathtaking scenery, Zena is a great starting point for hiking trails and skiing adventures. The surrounding mountains and lakes provide a stunning backdrop for outdoor activities and peaceful retreats. Visitors can appreciate the village’s historic sites and natural beauty, making Zena a tranquil destination for those looking to connect with nature while enjoying the charming local atmosphere.

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 from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.0°F (-3.9°C)Light RainMostly SunnySlightly LowSlightly High
February26.6°F (-3.0°C)Light RainMostly CloudyAverageSlightly High
March34.5°F (1.4°C)Light RainMostly SunnyAverageSlightly Low
April46.2°F (7.9°C)Light RainMostly SunnyAverageSlightly Low
May57.7°F (14.3°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighAverage
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighAverage
September62.6°F (17.0°C)Light RainMostly SunnySlightly HighSlightly Low
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November39.0°F (3.9°C)Light RainMostly SunnySlightly LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature is designed to help you plan your journeys effortlessly. Whether you're starting a new trip, picking up from where you last left off, or simply organizing your plans, this tool provides a dedicated space for you. You can easily access your previously saved and booked properties, which are neatly categorized into Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Delight in the lush landscape of Woodstock

Enjoy the art galleries and other features of Woodstock. Travelers to this relaxing city praise the hiking, forests and riverfront. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Woodstock

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Woodstock a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Indian Head Mountain (6.5 mi / 10.5 km)
  • Kaaterskill Falls (10.9 mi / 17.5 km)
  • Hunter Mountain (12.4 mi / 19.9 km)
  • Copperhood Retreat & Spa (13 mi / 20.9 km)
  • Mohonk Golf Course (18.1 mi / 29.2 km)
  • Windham Mountain Resort (18.6 mi / 30 km)

Exploring the natural features in Woodstock

Whether you're looking for adventure or just want to appreciate the scenery, Woodstock is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Overlook Mountain Trailhead (2.1 mi / 3.4 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (3.5 mi / 5.6 km)
  • Opus 40 (4.5 mi / 7.2 km)
  • Esopus Creek (8.7 mi / 14 km)
  • Saugerties Village Beach (8.8 mi / 14.2 km)
  • Falling Waters Preserve (9 mi / 14.5 km)

How to get to and around Woodstock

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.2 mi (43.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Woodstock when booking a vacation rental?
Zena is one of the most sought-after neighborhoods to book a vacation property in Woodstock. Spend your stay here to enjoy the privacy and comfort that comes with having a place to yourself.
What is the most popular type of vacation rental accommodation in Woodstock?
Apartments are the most popular kind of vacation rental in Woodstock, according to our data. Even if you’ve got something else in mind, Vrbo has vacation homes in all shapes and sizes. Look through our options to find your ideal match.
How much does it cost to rent a vacation rental in Woodstock?
Property type, season and length of stay are some factors that can affect the price of a vacation home. Simply add your travel dates to find your ideal match. From comfy cottages to expansive luxury villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in Woodstock?
Prices for beach houses in Woodstock can differ depending on the type and size of the property and when you’re traveling. Just enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use the filters to refine your search results by ratings, amenities and more.
Are there pet-friendly vacation rentals in Woodstock?
Pack a travel bag for the pup in your life because Woodstock has 47 vacation rentals that throw out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Woodstock?
Pack your swimwear and swim ring, because there are five houses with a private pool in Woodstock. Make a booking at one of these popular vacation rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find a place to make a splash!
What are popular rental amenities in Woodstock?
The most popular rental amenities people are looking for in Woodstock are a fireplace, a chef and a nearby river. Whether you’re hitting the road with your besties, family or even pets, Vrbo vacation rentals include the best amenities for starting a new adventure with the people you love.
Are there large group vacation rentals in Woodstock?
There are 11 vacation homes in Woodstock that can host five or more people. From family trips to special occasions, these stays have enough space to spend time with the people that matter the most.
Are there vacation rentals in Woodstock that welcome kids?
With 45 family-friendly vacation homes to select from in Woodstock, now is a great time to introduce the kids to the joys of travel. Just click on our “Properties good for families” filter to find stays loaded with amenities ideal for vacationing families, such as extra bedrooms, swimming pools, bunk beds and entertainment areas.
What are the top attractions for families in Woodstock?
You’ll find lots of cool things to see and do with the family in Woodstock, such as:

  • Overlook Mountain Trailhead
  • Saugerties Village Beach
  • Indian Head Mountain

Are there one-bedroom vacation rentals in Woodstock?
Yes, you’ll find 28 one-bedroom properties in Woodstock to choose from. A one-bedroom vacation rental is a superb choice if it’s just you and your sweetheart or if you’re flying solo. Add in more privacy, convenience and space compared to a hotel, and you’re bound to have a getaway to remember.
Can I find two-bedroom vacation rentals in Woodstock?
Woodstock has 11 two-bedroom vacation rentals for you to select from. Book a vacation home with all the privacy and comfort you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Woodstock?
You’ll have a choice of 21 vacation rentals with WiFi in Woodstock. If you want to disconnect from the world during your escape, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Woodstock?
Pick from 42 vacation rentals with air conditioning in Woodstock providing that cooling breeze and extra comfort level. Simply enter your dates of travel and then make use of our filters to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Woodstock?
It’s a good idea to check with the Woodstock vacation rental you’d like on Vrbo as the age limit differs. However, it’s generally 16, 18 or 21.
How long can I rent a vacation rental in Woodstock for?
The amount of time you can stay in a Woodstock vacation home for depends on each property. Just tap in your preferred travel dates to see options offering extended stays. They have everything you need to make your extended trip more convenient and enjoyable, such as air conditioning and kitchens. Some vacation homes might also offer weekly or monthly discounted prices, so you can stay longer for less money.

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