Photo by Marina Timo

Woodstock holiday lettings

We found 743 holiday rentals — enter your dates for availability

Discover a selection of 68 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:10 Oct - 17 Oct

Why visit Woodstock

  • Outdoor Adventures: Experience stunning nature reserves, ideal for hiking and exploration amidst breathtaking landscapes.
  • Historic Vibes: Discover the rich heritage of New Woodstock with its quaint historic sites and picturesque surroundings.
  • Charming Accommodations: Choose from a variety of delightful holiday homes, cosy cottages, and charming cabins for your stay.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment with activities suitable for visitors of all ages.
  • Scenic Waterfalls: Visit captivating waterfalls that enhance the natural beauty of the region.

Popular types of accommodation in Woodstock

If you're pondering on the ideal accommodation for your getaway in Woodstock, look no further! Our platform offers a delightful range of options, including private holiday homes, charming cabins, and cosy cottages. Whether you seek Woodstock holiday rentals, apartment options, or serene cabin retreats, we have something to suit every taste and budget. Explore our selection of Woodstock rentals and enjoy a memorable stay in this picturesque location!

  • Houses: The top choice for accommodation in Woodstock, ideal for families, friends, or couples seeking a home-away-from-home experience.
  • Cabins: A rustic and charming option, these retreats provide a peaceful escape surrounded by nature.
  • Cottages: Quaint and cosy, perfect for those wanting a romantic getaway or a tranquil retreat.
  • Apartments: Convenient and versatile, these rentals offer a comfortable stay with easy access to local amenities.
  • Chalets: A delightful choice, often featuring stunning views and a warm atmosphere for a unique holiday experience.**

Top attractions near Woodstock

Woodstock, New York, is a charming destination perfect for outdoor enthusiasts and adventure seekers. Visitors can explore captivating points of interest, including nature reserves, historic colleges, and picturesque waterfalls. This delightful town offers a blend of cultural experiences and family-friendly activities, ensuring an enjoyable getaway that showcases the stunning scenery and rich heritage of the area.

  • Bethel Woods Museum: Located 1.9km from Woodstock, this museum offers a rich cultural experience, celebrating the legacy of the 1969 Woodstock Festival and the arts, with engaging exhibits and events.
  • Bard College: Situated 6.8km away, this historic campus boasts stunning architecture and a vibrant arts scene, making it a perfect spot for cultural enrichment and leisurely strolls.
  • Kaaterskill Falls: This breathtaking waterfall, also 6.8km from Woodstock, is a must-visit for outdoor enthusiasts, offering scenic hiking trails and a romantic atmosphere amidst nature's beauty.

Things to do recommended for couples

For a romantic getaway in Woodstock, explore the thrilling slopes of Hunter Mountain, indulge in a rejuvenating treatment at Copperhood Retreat & Spa, or take an adventurous ride on the H Ski Lift. Each experience promises to create unforgettable memories together in this charming town.

Things to do recommended for families

Families visiting Woodstock can unwind at Saugerties Village Beach, a lovely recreation park, or enjoy the sporting atmosphere at Dietz Stadium. For some thrilling fun, the Kiwanis Ice Arena offers ice skating adventures, making it a perfect day out for the whole family.

Things to do recommended for groups

Groups visiting Woodstock can hike the Overlook Mountain Trailhead for breathtaking views, explore musical treasures at the Woodstock Music Shop, and enjoy a round of golf at the scenic Woodstock Golf Club, perfect for outdoor enthusiasts and sports lovers alike.

Booking with Vrbo is a breeze

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can frequently result in significant savings. To discover the ideal Vrbo accommodation that suits your budget, make use of our filters to search by price, location, and type of holiday rental.

Where to stay near Woodstock

Woodstock, New York, offers a delightful blend of outdoor adventure and serene landscapes, perfect for a relaxing getaway. Explore the charming town with its family-friendly atmosphere and friendly locals. Nearby, discover the historical vibes of New Woodstock and other picturesque regions that promise scenic views and a sense of seclusion. Whether you're seeking a peaceful retreat or an urban escape, Woodstock is an ideal destination for your next holiday adventure.

  • Kingston: Located a mere 6.2km from Woodstock, Kingston is a city steeped in history and natural beauty. Renowned for its outdoor adventures, visitors can engage in skiing at nearby resorts and explore scenic mountain trails. The city's rich heritage is highlighted by landmarks such as historic colleges and picturesque lakes, making it an ideal destination for those seeking both adventure and culture. Kingston’s vibrant arts scene and charming downtown area offer delightful dining options and boutique shopping, ensuring a well-rounded travel experience.
  • Saugerties: Just 5.6km from Woodstock, Saugerties is a charming city that captivates visitors with its picturesque landscapes and outdoor pursuits. Known for its adventure offerings, the area boasts excellent skiing facilities and access to stunning mountains and lakes. Saugerties also features a lively atmosphere with local events and attractions, including a community stadium. With its blend of natural beauty and recreational opportunities, Saugerties is perfect for those looking to immerse themselves in the great outdoors while enjoying a friendly, small-town vibe.
  • Bearsville: A stone's throw from Woodstock, at only 1.2km away, Bearsville is a quaint community celebrated for its scenic beauty and outdoor activities. This picturesque locale is ideal for adventure seekers, with opportunities for skiing and exploration within nearby national and state parks. Visitors can revel in the stunning views of mountains and lakes, making Bearsville a haven for nature lovers. The close proximity to Woodstock allows for easy access to local arts and culture, ensuring a delightful experience for all who visit.

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

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

Regardless of whether you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s important to filter based on your specific priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many, a family holiday isn’t truly fulfilled 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 in search of holiday rentals offering discounts 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 options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated area to plan new trips, pick up from where you last left off, or review and arrange your travel plans. You can now easily access the properties you’ve saved or booked, organised into Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/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. Hunter Mountain and Catskill Mountains are just a couple of the must-see attractions in the area. 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:

  • Hunter Mountain (12.4 mi / 19.9 km)
  • Indian Head Mountain (6.5 mi / 10.5 km)
  • Kaaterskill Falls (10.9 mi / 17.5 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)
  • Saugerties Village Beach (8.8 mi / 14.2 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 rental?
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 rental accommodation in Woodstock?
Apartments are the most popular kind of holiday rental in Woodstock, according to our data. Even if you've got something else in mind, Vrbo 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 rental 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 Vrbo holiday 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 travelling. 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 holiday rentals in Woodstock?
Pack a travel bag for the pup in your life because Woodstock has 47 holiday 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 holiday 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 holiday 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 holiday rentals include the best amenities for starting a new adventure with the people you love.
Are there large group holiday rentals 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 rentals 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 rentals in Woodstock?
Yes, you'll find 28 one-bedroom properties in Woodstock to choose from. A one-bedroom holiday 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 holiday rentals in Woodstock?
Woodstock has 11 two-bedroom holiday rentals for you to select from. Book a holiday home with all the privacy and comfort you want at an attractive price on Vrbo.
Are there holiday rentals with WiFi in Woodstock?
You'll have a choice of 21 holiday 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 holiday rentals with air conditioning in Woodstock?
Pick from 42 holiday 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 holiday rental in Woodstock?
It's a good idea to check with the Woodstock holiday 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 holiday rental 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.

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