Woodstock vacation rentals

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Welcome to the enchanting town of Woodstock, where rustic charm meets breathtaking natural beauty. Nestled amidst stunning waterfalls and vibrant outdoor adventures, this serene destination invites travelers to immerse themselves in its rich culture and history. With a variety of family-friendly activities and diverse accommodations ranging from cozy cottages to spacious homes, Woodstock ensures comfort and convenience for groups of all sizes. Enjoy the warmth and amenities of a vacation rental, creating a home-like experience in this idyllic getaway.

Holiday rentals with weekly discounts - Woodstock

Showing deals for:Feb 5 - Feb 12

Image gallery for Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Living area
10 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Phoenicia

19% off
Price is $170
$1,193 for 7 nights
All fees included
Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

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Find out more about Woodstock

Why visit Woodstock

  • Stunning natural scenery: Explore beautiful nature preserves and waterfalls that showcase the area's breathtaking landscapes.
  • Cultural experiences: Immerse yourself in the vibrant arts scene and historic sites that reflect Woodstock's rich history.
  • Charming local shops: Wander through the quaint streets and discover unique boutiques and artisan stores.
  • Cozy accommodations: Choose from a variety of lodging options, including rustic cabins and charming cottages, perfect for relaxation.
  • Welcoming atmosphere: Enjoy the friendly vibe and vibrant dining spots that make Woodstock a memorable destination.

Popular types of accommodation in Woodstock

Planning a getaway to Woodstock? You're in for a treat. Discover the charm of this vibrant village with a range of accommodation options, including cozy houses, rustic cabins, and charming cottages. Whether you're looking for townhouse rentals, spacious house rentals, or even hostels, Woodstock has something for everyone. Enjoy your stay and experience the unique spirit of this iconic destination.

  • Houses: The top choice for travelers to Woodstock, these homes offer spacious accommodations for families and groups seeking comfort and privacy.
  • Cabins: A close second, cabins provide a rustic experience in nature, ideal for those looking to escape the hustle and bustle.
  • Cottages: Perfect for a quaint getaway, cottages offer charm and intimacy for couples or solo travelers.
  • Apartments: A convenient option, apartments provide a homely feel in the heart of Woodstock.
  • Chalets: These stylish retreats combine comfort with stunning views, making them a popular choice for a unique stay.**

Top attractions near Woodstock

Woodstock, New York, is the perfect destination for outdoor enthusiasts and adventure seekers. With its stunning scenery, visitors can explore local attractions like nature preserves, beautiful waterfalls, and historic colleges. Whether you're traveling with family or seeking a cultural experience, Woodstock offers a range of activities that cater to all interests, making it an ideal spot for a memorable vacation.

  • Bethel Woods Museum: Located 3 miles from Woodstock, this museum celebrates the cultural history of the 1969 Woodstock Festival. You’ll find exhibits showcasing music, art, and the peace movement, all set against a beautiful landscape that enhances its cultural vibes.
  • Kaaterskill Falls: Situated 11 miles from Woodstock, this stunning waterfall is perfect for outdoor adventures and romantic outings. With its picturesque views and hiking trails, Kaaterskill Falls offers a refreshing escape into nature.
  • Bard College: Also 11 miles away, Bard College is a historic institution known for its beautiful campus and vibrant arts scene. It’s a hub of culture, featuring galleries, performances, and lectures that engage visitors.

Things to do recommended for couples

For a romantic getaway in Woodstock, consider skiing at Hunter Mountain, indulging in relaxation at Copperhood Retreat & Spa, or enjoying a wine tasting at El Paso Winery. Each offers a unique vibe perfect for couples seeking adventure, wellness, and romance.

Things to do recommended for families

Your family vacation in Woodstock, NY, can include a fun day at Saugerties Village Beach for relaxation, cheering at a game at Dietz Stadium, or enjoying ice skating at Kiwanis Ice Arena. Each spot offers unique vibes perfect for family adventures.

Things to do recommended for groups

In Woodstock, groups can hike the scenic Overlook Mountain Trailhead for outdoor adventure, browse unique finds at the Woodstock Music Shop, and enjoy a round of golf at the Woodstock Golf Club for a fun day of sports and relaxation.

*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

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like food bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Woodstock: If you're searching for vacation rentals offering 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 rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Woodstock

Woodstock, New York, offers a delightful blend of relaxation and adventure for every traveler. Explore the charming streets and local shops, unwind at scenic outdoor spots, or visit family-friendly attractions nearby. Don’t miss the vibrant watering holes and cozy eateries that showcase the town's friendly atmosphere. With its rich history and welcoming vibe, Woodstock is the perfect destination for a memorable vacation experience.

  • Kingston: Located 10 miles from Woodstock, Kingston is a vibrant city known for its outdoor adventures and ski experiences. Nestled between the scenic Hudson River and the Catskill Mountains, Kingston offers a plethora of activities, including skiing at nearby ski resorts. Travelers can explore the historic downtown area, which features charming shops, restaurants, and local art. The nearby landmarks, such as the beautiful Kingston Point Beach and the historic college university, enhance the travel experience, making it a must-visit for those looking to immerse themselves in nature and history.
  • Saugerties: Situated 9 miles from Woodstock, Saugerties is a delightful city that attracts outdoor enthusiasts and adventure seekers. Known for its stunning mountain views and proximity to ski resorts, Saugerties offers a range of activities from skiing to hiking. Visitors can enjoy the picturesque Hudson River waterfront, explore the local stadium, and wander through the charming streets filled with boutiques and eateries. The vibrant arts scene and beautiful natural surroundings make Saugerties an ideal destination for those looking to connect with nature while enjoying cultural experiences.
  • Bearsville: Just 2 miles from Woodstock, Bearsville is a quaint community known for its breathtaking scenery and outdoor adventures. Surrounded by mountains and lakes, it offers excellent opportunities for skiing and exploring the nearby national state park. Travelers can enjoy picturesque landscapes, vibrant wildlife, and a peaceful atmosphere perfect for relaxation. Bearsville’s close-knit vibe, combined with outdoor activities, makes it an inviting stop for those seeking a tranquil escape while still being close to the artistic and cultural offerings of Woodstock.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageSlightly Low
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 HighAverage
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 getaway? Being open to adjusting your travel dates can really help, as prices tend to vary. Additionally, if you book a longer stay, you often unlock significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform to help you plan your travels, allowing you to create new trips, resume your previous plans, or easily organize your itinerary. You'll see your saved or booked properties neatly categorized as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Enjoy the natural beauty of a Woodstock house for rent

This mountain town shares the name with an iconic music festival, and still embraces the peaceful bohemian atmosphere. Innovative live music performed at Bearsville Theater and Levon Helm Studios keeps the festival's spirit alive. Throughout the area, you can stop in boutique shops selling tie-dye T-shirts and New Age jewelry. The Elena Zang Gallery and several others around town showcase the works of local artists. As with all rental houses in the Catskills, Woodstock's lodgings accentuate the area's natural beauty. The vaulted ceilings and tall windows allow the sunlight in and give you a view of the outdoors

 

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:

  • Hunter Mountain (11.1 mi / 17.8 km)
  • Woodstock Music Shop (0.1 mi / 0.1 km)
  • Kaaterskill Falls (10.9 mi / 17.5 km)
  • Mohonk Golf Course (18.1 mi / 29.2 km)
  • Windham Mountain Resort (19.2 mi / 30.9 km)
  • Woodstock Golf Club (0.5 mi / 0.8 km)

Adventure abounds in Woodstock

The Catskill Mountains provide a wealth of hiking trails to explore, whether you prefer to take a gentle saunter or to tackle something more challenging. The trail up to Kaaterskill Falls is one of the easiest, but the 1.7-mile-long round trip takes you past spectacular falls—the highest 2-step waterfall in the state. Head up to Hunter Mountain for an exciting day out. In the winter, you can enjoy skiing and snowboarding across 58 trails, and during the summer you can enjoy an adrenaline-pumping zipline adventure, or traverse the hills in a thrilling 4x4 tour.

Woodstock—a year-round destination

If you want to take advantage of the nearby skiing and snowboarding, Woodstock vacation rentals are perfect in winter, when temperatures drop to as low as 13 degrees and the area experiences the most snowfall. If you prefer to explore the great outdoors in warmer weather, June through August is one of the best times to visit, with temperatures of around 65-70 degrees. The shoulder seasons also provide pleasant conditions for enjoying the outdoor pursuits on offer. May through September enjoy mild conditions, with the mercury hovering around the 60-degree mark.

Awe-inspiring vistas await in Woodstock

You never have to stray far from Woodstock vacation rentals to enjoy the wealth of hiking provided by the Catskill Mountains. Gorgeous areas like Bluestone Wild Forest and Indian Head Wilderness are home to fantastic trails and bouldering, and also boast breathtaking falls—the sight of which will make even the most challenging hike well worth the effort. Water lovers will enjoy the area, too. The Ashokan Reservoir and Hudson River are both close by, and there are also numerous watering holes for swimming, such as the picturesque Millstream.

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, New York, United States of America when booking a vacation rental?
When booking a vacation rental in Woodstock, New York, the best area to consider is the vibrant central part of town. This area is known for its artistic charm and close proximity to numerous attractions. You can easily explore the iconic Woodstock Playhouse, which hosts a variety of performances, and take a stroll through the picturesque Woodstock Village Green, where local events often take place.

Additionally, the surrounding neighborhoods offer a range of properties, from cozy cabins to more modern rentals, making it easy to find something that suits your needs. Each area has its own unique character, allowing visitors to experience the local art scene and enjoy outdoor activities.
How much does it cost to rent a vacation home in Woodstock?
Prices for vacation 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 vacation 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 the best ski resort rentals near Woodstock, travelers should focus on properties in the nearby town of Hunter, which is home to Hunter Mountain Ski Resort. This area features a variety of rental options, including cozy chalets and spacious cabins that cater to families and groups. Many of these properties come with amenities such as fireplaces, hot tubs, and fully equipped kitchens, great for unwinding after a day on the slopes.

In Woodstock itself, travelers can find charming rentals that reflect the town's artistic vibe, often housed in historic buildings or unique structures. These accommodations typically offer inviting living spaces, outdoor decks, and proximity to local shops, galleries, and restaurants that capture the spirit of the area.

Additionally, the surrounding Catskill Mountains provide numerous outdoor activities beyond skiing, with options for hiking and snowshoeing during the winter months. Rentals in the vicinity often feature easy access to these natural attractions, making them ideal for travelers looking to combine winter sports with scenic exploration.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular type of rental, with about 52 available throughout the area. These homes are often situated in scenic locations, providing a peaceful retreat for visitors looking to immerse themselves in nature. Most vacation houses come equipped with full kitchens, spacious living areas, and outdoor decks or patios where guests can relax and enjoy the beautiful surroundings. Additionally, there are around 17 cottages available, which offer a charming and cozy atmosphere, ideal for couples or small families. Cottages typically feature rustic décor, kitchenette facilities, and sometimes access to private gardens. For those seeking unique stays, there are several apartments, cabins, and chalets that provide a variety of amenities such as fireplaces, hot tubs, and beautiful views of the Catskill Mountains.
Are there any family house rentals in Woodstock?
In Woodstock, New York, there are numerous family-friendly house rentals available, with around 67 options to choose from. The town is renowned for its artistic vibe and natural beauty, making it a superb getaway for families. Many of these homes offer spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces for kids to enjoy.

In terms of amenities, you can expect features such as game rooms, cozy fireplaces, and even private decks or patios for relaxing after a day of exploring. Families will appreciate the proximity to local attractions, including the picturesque Woodstock town center, where you'll find charming shops and eateries. Nearby outdoor activities abound, including hiking trails in the Catskill Mountains, which are great for family adventures. See all family-friendly rentals in Woodstock.
Can I rent a vacation home with a pool or hot tub in Woodstock?
In Woodstock, New York, there are several vacation homes available for rent that feature pools and hot tubs, with around 26 options to choose from. This picturesque town in the Catskills is known for its artistic vibe and natural beauty, making it a great destination for relaxation and outdoor activities. Many of these properties come with amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, great for both fun and comfort.

Travelers can expect a variety of settings, from rustic cabins located in the woods to modern homes with stunning mountain views. Some rentals may also include features like fire pits, barbecue areas, and large gardens, enhancing the overall vacation experience.
Can I find long-stay vacation rentals in Woodstock?
A long-stay vacation rental in Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, there are numerous pet-friendly house rentals available, offering a variety of amenities to suit travelers' needs. Many of these rentals come equipped with spacious outdoor areas, allowing pets to roam freely, as well as cozy interiors featuring modern kitchens, comfortable living spaces, and sometimes even fireplaces for those cooler evenings.

The town itself is surrounded by beautiful natural landscapes, making it an inviting destination for pet owners who enjoy outdoor activities. Nearby parks and hiking trails, such as the scenic Overlook Mountain and the expansive Catskill Park, provide excellent opportunities for walking and exploring with your furry companions. Woodstock also has charming local shops and pet-friendly cafes, adding to the overall experience for travelers with pets.
Are there any remote work vacation rentals in Woodstock?
In Woodstock, New York, there are numerous remote work vacation rentals available, with around 81 options to choose from. This charming town, known for its artistic community and natural beauty, provides a conducive environment for remote work. Many rentals come equipped with reliable Wi-Fi, both in-room and in common areas, ensuring seamless connectivity for work-related tasks. Additionally, some properties offer dedicated office spaces, which can enhance productivity during your stay.

The town itself is surrounded by stunning landscapes, including the nearby Catskill Mountains, making it an ideal location for both work and leisure. After a day of work, travelers can explore local attractions like the Woodstock Artists Association & Museum or enjoy hiking trails in the area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woodstock vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodstock with parking available—perfect for families or travelers 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 vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, as well as outdoor decks or patios for enjoying the serene natural surroundings. Many rentals also feature cozy fireplaces, superb for warming up during cooler evenings. Onsite parking is commonly available, making it convenient for travelers with vehicles. Additionally, many properties provide coffee and tea makers, ensuring that guests can start their day with a warm beverage.
When is the best time to visit Woodstock for a vacation rental?
July is the most popular time to visit Woodstock, drawing travelers eager to immerse themselves in the vibrant summer atmosphere. This peak season, which spans from July to September, offers a wealth of activities, including outdoor concerts, art festivals, and the chance to explore the beautiful Catskill Mountains. With warm temperatures typically ranging from the mid-50s to mid-80s Fahrenheit, visitors can comfortably enjoy hiking, biking, and leisurely strolls through the charming town.

In July, Woodstock comes alive with events that celebrate the arts and music scene, providing ample opportunities for sightseeing and engaging with the local community. The lush greenery and picturesque landscapes make it an ideal setting for outdoor enthusiasts and those seeking a creative escape.

For those looking for a more budget-friendly experience, consider planning your visit in November. This quieter month allows you to appreciate the serene beauty of Woodstock as the fall foliage transitions into a peaceful winter landscape. While the pace may be slower, November offers a unique charm superb for cozying up in a vacation rental and enjoying the local culture without the crowds.
How early should I book a Woodstock vacation rental?
Book your Woodstock vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodstock, New York, United States of America?
In Woodstock, visitors can engage in a rich artistic and cultural scene. The town is famous for its connection to the 1969 music festival, with the original site located nearby in Bethel. The vibrant village center features unique shops, art galleries, and local eateries, making it a superb spot for exploration.

One of the main attractions is the Woodstock Artists Association & Museum, which showcases the work of local artists and hosts various exhibitions throughout the year. For nature lovers, the nearby Overlook Mountain offers hiking trails that lead to stunning views and the remnants of a historic hotel.

Additionally, the iconic Woodstock Town Park provides scenic walking paths, picnic areas, and access to the Sawkill Creek, superb for a relaxing day outdoors.
Can I change or cancel my Woodstock home rental booking on Vrbo?
To find Woodstock vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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