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Woodstock, NY Vacation Rentals

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 Index in Woodstock

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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 cheapest day to stay at a vacation rental in Woodstock tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Woodstock tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The weather in Woodstock

56º -1º
73º 12º
86º 26º
93º 32º
93º 43º
92º 50º
90º 48º
91º 40º
80º 30º
72º 14º
59º -4º
Rainy days
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This climate histogram shows you the weather patterns in Woodstock. The hottest month in Woodstock is August, when temperatures peak at 93 ˚F. The coolest month is December, when temperatures drop to -4 ˚F. The wettest month in Woodstock is August with 5.06 inches of rain, while the driest month is November with 0.82 inches of rain.

Vacation Rentals in Woodstock

Browse accommodations from all the best providers including Airbnb, Homeaway, VRBO and more at AllTheRooms.com. We have 507 vacation rentals, hotels and other accommodation types in Woodstock ranging from budget options to luxury places to stay. A trip to Woodstock can be affordable - our lowest price accommodation is available at $59 per night. The average price of accommodation in is $253 per night.

If you want to stay connected during your trip, then you can choose from over 401 accommodations in Woodstock that have WiFi. 50 of our accommodations in include a breakfast in the price. Choose from 19 places to stay that provide gym facilities, so you won't miss a single workout. If you are driving to Woodstock, you'll want to pick from 386 places to stay that provide parking. 50 hotels and vacation rentals have a pool or jacuzzi.

AllTheRooms has 185 pet-friendly places to stay in Woodstock, so if you're travelling with your cat or dog you won't have any trouble.

We combine a wide variety of Woodstock accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 272 places to stay from Airbnb, 61 accommodations from Homeaway and 56 places to stay from VRBO.

409 accommodations in Woodstock have been reviewed: 82% are rated excellent or good. 193 places to stay in are instantly bookable.

Destinations near Woodstock

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