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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

60º 16º
74º 22º
90º 38º
94º 46º
94º 51º
93º 55º
93º 44º
81º 28º
63º 13º
62º -14º
Rainy days
This climate histogram shows you the weather patterns in Woodstock. The hottest month in Woodstock is June, when temperatures peak at 94 ˚F. The coolest month is January, when temperatures drop to -14 ˚F. The wettest month in Woodstock is August with 8.52 inches of rain, while the driest month is March with 2.23 inches of rain.

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Vacation Rentals in Woodstock

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Homeaway, VRBO and more. Woodstock has 508 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those trying to keep costs down, the lowest priced place to stay in Woodstock comes in at $59 per night. A typical accommodation in Woodstock costs on average $246 per night.

If you want to stay connected during your trip, then you can choose from over 389 accommodations in Woodstock that have WiFi. 42 of our accommodations in include a breakfast in the price. You can keep up with your workout regime by staying at one of 18 accommodations that provide gym facilities. Driving to Woodstock? Then choose one of the 378 places to stay that comes with a parking spot included. 49 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 176 pet-friendly accommodations available.

AllTheRooms aggregates vacation rentals, hotels and other unique accommodation types from 5 providers in Woodstock, including 268 places to stay from Airbnb, 57 accommodations from Homeaway and 53 places to stay from VRBO

411 of our accommodations in Woodstock have been reviewed and rated. 82% are rated excellent or good. You can instantly book any of 208 places to stay right now.