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
90° 41°
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97° 56°
3
91° 48°
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92° 38°
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88° 30°
5
70° 15°
3
54°
4
59° -4°
4
61° -3°
2
72°
2
78° 20°
4
88° 40°
5
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Rainy days

This climate histogram shows you the weather patterns in Woodstock. The warmest months in Woodstock are June and April, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to -4 ˚F. The wettest month in Woodstock is March with 5.33 inches of rain, while the driest month is April with 1.08 inches of rain.

What Expert Travelers Think

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  • — 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!

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Vacation Rentals in Woodstock

Browse vacation rentals from all the best providers including Airbnb, Priceline, Hostelworld and many more at AllTheRooms.com. We have 520 vacation rentals, hotels and other places to stay in Woodstock ranging from cheap options to extravagant places to stay. A vacation in Woodstock can be budget-friendly - the cheapest price rental is available at $20 per night. The average price of a vacation rental is $255 per night.

Those needing to get some work done during their trip to Woodstock can pick from 303 places to stay that include WiFi. 38 places to stay include a breakfast. You can maintain your workout regime by staying at one of 6 accommodations that provide gym facilities. If you're planning on arriving in Woodstock by car, be sure to choose from 299 accommodations that provide parking. We track 47 hotels and vacation rentals that have 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 the places to stay in Woodstock have been reviewed by previous guests. They rated 87% as excellent or good. You can instantly book any of 215 places to stay right now.

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