Woodstock holiday rentals

We found 753 holiday rentals — enter your dates for availability

Discover a selection of 74 homes, 13 apartments and other holiday rentals in Woodstock that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Woodstock

Showing deals for:2 Oct - 9 Oct

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Why visit Woodstock

  • Scenic Natural Reserves: Explore pristine waterfalls and breathtaking landscapes that offer serene outdoor retreats.
  • Equestrian Adventures: Enjoy horseback riding through the picturesque countryside, perfect for adventure enthusiasts.
  • Cultural Heritage: Immerse in Woodstock’s rich history and vibrant community spirit through its local attractions.
  • Charming Neighbourhoods: Wander through quaint streets and hidden gems like Rooty Hill, capturing the city's unique essence.
  • Diverse Experiences: Relish both relaxing escapes and lively urban scenes, making Woodstock a versatile holiday destination.

Popular types of accommodation in Woodstock

Discover Woodstock, New York—a charming city offering a blend of art, music, and nature. Experience the magic through unique holiday rentals, including private holiday homes, cosy cabins, and quaint cottages. Explore local attractions and landmarks that capture the spirit of Woodstock, ensuring a memorable retreat in this culturally rich destination.

  • Private Holiday Homes: The top choice for visitors, offering spacious, self-contained retreats.
  • Cabins: The second favourite, these lodgings provide a cosy, rustic escape.
  • Cottages: The third most selected, offering charming, quaint abodes.
  • Apartments: Fourth in popularity, these modern, compact flats are ideal for a relaxed stay.
  • Chalets: The fifth option, providing comfortable, alpine-style lodgings.**

Top attractions near Woodstock

Woodstock, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Visitors can explore scenic reserves and pristine waterfalls, offering breathtaking views and tranquil experiences. The local equestrian centre invites adventure seekers to enjoy horseback riding through the beautiful landscapes. With a rich cultural backdrop, Woodstock provides a delightful blend of nature and community spirit, making it an ideal spot for a memorable holiday.

  • HITS-on-the-Hudson: A splendid equestrian centre, located 14km from Woodstock, offering delightful rides amidst verdant surroundings.
  • Esopus Creek: A picturesque river with outdoor, scenic vibes, found 14km from Woodstock, perfect for a tranquil day out.
  • Opus 40: A unique sculpture garden with family-friendly, outdoor experiences, situated 6km from Woodstock, ideal for art and nature enthusiasts.

Things to do recommended for couples

Embrace a romantic retreat in Woodstock, where you can wander through charming streets and enjoy scenic countryside views, perfect for a couple's getaway.

Things to do recommended for families

Families will delight in exploring local art galleries, participating in interactive craft workshops and enjoying scenic walks in Woodstock's charming countryside.

Things to do recommended for groups

Explore the vibrant art scene at the Woodstock Artists Association & Museum, or take a scenic hike along the picturesque trails of Overlook Mountain. For a unique experience, enjoy a group yoga session at a local studio, embracing the serene atmosphere of this charming town.

*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

If you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to prioritise your filters accordingly. Here are some helpful booking tips from Stayz for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or an outdoor area for group gatherings. Luckily, you can easily apply filters for all these options and more on Stayz.
  • Traveling to Woodstock with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many, a family holiday wouldn’t be complete without their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of holiday rentals that offer discounts for stays of a month or longer, you've come to the right site. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in and around Woodstock

Discover Woodstock, New York, where nature meets history in a delightful blend of outdoor adventures and serene retreats. Stroll through charming neighbourhoods, explore hidden gems on Rooty Hill, and immerse yourself in the friendly, family-oriented atmosphere. Whether you're seeking a relaxing escape or a vibrant urban experience, Woodstock beckons with its inviting landscapes and rich cultural heritage.

  • Kingston: Situated 16km from Woodstock, this city offers an invigorating blend of outdoor pursuits and adventure. Kingston is renowned for its skiing opportunities with expansive ski fields, and its welcoming ski resorts. Visitors can enjoy a scenic mountain backdrop and a sparkling lake, while also exploring the historical charm of a nearby college campus. This city promises a well-rounded travel experience for those seeking both adventure and cultural enrichment.
  • Saugerties: Located 14km from Woodstock, Saugerties presents a dynamic mix of adventure and outdoor excitement. This city is a haven for skiing enthusiasts, boasting impressive ski fields and ski resorts. The majestic mountain and serene lake provide a picturesque setting, while a local stadium offers a touch of communal spirit. Saugerties is perfect for travellers keen to experience both the thrill of the slopes and the beauty of natural landscapes.
  • Shady: Nestled within the Woodstock area, the village of Shady offers a more intimate exploration of the outdoors. Known for its adventure and scenic vistas, this locale features inviting hiking trails and ski fields. The natural allure is enhanced by nearby mountains and a tranquil lake, alongside a historic site that adds a layer of cultural interest. Shady is an ideal destination for those seeking a blend of outdoor activity and a taste of local history.

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 Stayz is simple

Looking to cut costs on your upcoming journey? Flexibility with your travel dates can be beneficial, as prices do vary. Additionally, opting for a longer stay can often lead to significant savings. To find the ideal Stayz property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday let.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board offers a practical platform for you to plan new trips, resume your previous arrangements, or manage your travel plans effortlessly. You can easily access your saved or booked properties, which are organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Delight in the lush landscape of Woodstock

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

Activities and attractions in and around Woodstock

Are you looking for top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Woodstock a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 an outdoor enthusiast or just want to spend some time taking in the scenery, Woodstock is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Catskill Mountains (13.7 mi / 22.1 km)
  • 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)
  • Forsyth Park (8.8 mi / 14.1 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 centre.

Frequently asked questions

What is the best area to stay in Woodstock when booking a holiday home?
Zena is one of the most sought-after neighbourhoods to book a holiday 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 holiday home accommodation in Woodstock?
Apartments are the most popular kind of holiday home in Woodstock, according to our data. Even if you've got something else in mind, Stayz has holiday homes in all shapes and sizes. Look through our options to find your ideal match.
How much does it cost to rent a holiday home in Woodstock?
Property type, season and length of stay are some factors that can affect the price of a holiday home. Simply add your travel dates to find your ideal match. From comfy cottages to expansive luxury villas, all Stayz holiday homes 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 travelling. Just enter your travel dates into Stayz 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 holiday homes in Woodstock?
Pack a travel bag for the pup in your life because Woodstock has 47 holiday homes that throw out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Stayz. 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 holiday homes and every day can be a pool day. Simply enter your travel dates into Stayz, then use the "pool" filter to find a place to make a splash!
What are popular home amenities in Woodstock?
The most popular home 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, Stayz holiday homes include the best amenities for starting a new adventure with the people you love.
Are there large group holiday homes in Woodstock?
There are 11 holiday 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 holiday homes in Woodstock that welcome kids?
With 45 family-friendly holiday 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 holidaying 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 holiday homes in Woodstock?
Yes, you'll find 28 one-bedroom properties in Woodstock to choose from. A one-bedroom holiday home 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 holiday homes in Woodstock?
Woodstock has 11 two-bedroom holiday homes for you to select from. Book a holiday home with all the privacy and comfort you want at an attractive price on Stayz.
Are there holiday homes with WiFi in Woodstock?
You'll have a choice of 21 holiday homes 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 Stayz.
How can I find holiday homes with air conditioning in Woodstock?
Pick from 42 holiday homes 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 holiday home in Woodstock?
It's a good idea to check with the Woodstock holiday home you'd like on Stayz as the age limit differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Woodstock for?
The amount of time you can stay in a Woodstock holiday 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 holiday homes might also offer weekly or monthly discounted prices, so you can stay longer for less money.