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Woodstock, NY Vacation Rentals

Our Favorite Vacation Rentals in Woodstock

Woodstock Vacation Rentals with a Pool

Woodstock Vacation Rentals with Wi-Fi

Woodstock Pet-Friendly 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 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 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 Weather in Woodstock

94º 51º
93º 55º
93º 44º
81º 28º
63º 13º
62º -14º
60º 16º
74º 22º
90º 38º
94º 46º
Rainy days
This climate histogram shows you the weather patterns in Woodstock. The warmest months in Woodstock are June and July, when temperatures reach 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.

What Expert Travelers Think

Vacation Rentals in Woodstock

At we have vacation rentals from all of your favorite providers - Airbnb, Bed and Breakfast, Hostelworld and more. We have 508 vacation rentals, hotels and other accommodation types in Woodstock ranging from cheap options to luxury places to stay. A vacation in Woodstock can be budget-friendly - the lowest price accommodation is available at $20 per night. On average, a place to stay in Woodstock will cost you $244 per night.

If you would like to stay connected during your trip, then you can choose from over 390 accommodations in Woodstock that have WiFi. 40 of our accommodations come with breakfast in the price. Choose from 12 accommodations that provide gym options, so you won't miss a single workout. Driving to Woodstock? Then choose one of the 380 places to stay that comes with a parking spot included. 47 places to stay have a a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 174 pet-friendly accommodations available.

416 of our rentals in Woodstock have been reviewed by previous guests. They rated 82% as excellent or good. 196 accommodations allow instant booking.

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