Woodstock, NY Vacation Rentals

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Woodstock, New York Travel Guide

Before you get excited, the world-famous 1969 Woodstock music festival actually took place in Bethel, a town 60 miles away from Woodstock. That being said, the town itself is a leafy haven for culture junkies with an incredibly rich arts scene. It’s a romantic town settled in the Catskill Mountain range and has been the source of inspiration for tons of musicians over the decades. Woodstock has an iconic small-town feel as it’s resisted development from hotel chains and even cell towers -- so don’t expect your phone signal to be impeccable. But if you’re looking for a little bucolic getaway, Woodstock is one of New York’s finest gems.

Things to Do in Woodstock, New York

One of the best things to do in Woodstock is go shopping along Tinker Street and Mill Hill road. The colorful street is filled with quirky mom-and-pop shops that make up the town’s vibe. Browse vintage bookstores, boutique chocolate stores, and arts and craft shops. Listening to live music is another great thing to do here, as the town still carries much of the novelty and pride of the festival that happened almost 50 years ago. When you don’t have anything to do, go people watching in the town center, Village Green, or hike up to Overlook Mountain for some great views. And, for a peaceful retreat from everything, visit the Karma Triyana Dharmachakra, a monastery that looks like it’s been plucked from the Himalayan countryside.

Best Time to Visit Woodstock, New York

Summertime in Woodstock is definitely the best time to visit. The weather is nice, the shops are open, and the town's energy really comes alive. Don't be afraid to visit during the shoulder months of spring or fall for a chillier break.

Price and Availability in Woodstock

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The cheapest day to stay at a vacation rental in Woodstock tends to be Wednesday, while the most expensive day tends to be Friday. Vacation homes in Woodstock tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Woodstock is in August, while the cheapest month is in March. The most popular time to book a vacation rental in Woodstock is in the high season in August. Woodstock has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Woodstock

Rainy days
92° 34°
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98° 43°
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93° 50°
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95° 51°
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87° 44°
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79° 34°
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69° 18°
1
67° 16°
2
51°
1
52°
2
80° 14°
2
84° 20°
2
May
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Rainy days

This climate histogram shows you the weather patterns in Woodstock. The warmest months in Woodstock are July and May, when temperatures reach 98 ˚F. The coolest month is December, when temperatures drop to 3 ˚F. The wettest month in Woodstock is April with 9.78 inches of rain, while the driest month is December with 1.23 inches of rain.

What Expert Travelers Think

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

Vacation Rentals in Woodstock

Browse accommodations from all the leading providers including Airbnb, Priceline, Hostelworld and others at AllTheRooms.com. We have 520 vacation rentals, hotels and other places to stay in Woodstock ranging from inexpensive options to extravagant places to stay. If you are trying to save money, the cheapest place to stay in Woodstock is only $20 a night. An average accommodation in Woodstock costs on average $255 a night.

Those looking to get some work done during their trip to Woodstock can choose from 303 places to stay that have WiFi. 38 places to stay include a morning meal. Fitness addicts can get a workout in during their stay by choosing from 6 accommodations that have gym facilities. If you're planning on arriving in Woodstock by car, be sure to choose from 299 accommodations that provide parking. 47 places to stay come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 122 accommodations that are designated as pet-friendly.

439 of our accommodations in Woodstock have been reviewed and rated. 87% are rated excellent or good. 215 places to stay in are instantly bookable.

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