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

Pick the perfect vacation rental for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Hostelworld and others. AllTheRooms has 520 vacation rentals, hotels and other great places to stay during your time in Woodstock, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. If you are wanting to keep costs down, the cheapest place to stay in Woodstock comes in at $20 per night. An average accommodation in Woodstock costs on average $255 a night.

Those looking to get some work finished during their trip to Woodstock can pick from 303 places to stay that provide WiFi. We have 38 accommodations that include a breakfast included. Choose from 6 accommodations that provide gym options, so you don't miss a single workout. If you are driving to Woodstock, you'll want to pick from 299 places to stay that provide parking. We have 47 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 122 pet-friendly places to stay in Woodstock, so if you're traveling with your pet you won't have any problems.

439 of our places to stay in Woodstock have been reviewed by previous guests. They rated 87% as great. You can instantly book any of 215 places to stay right now.

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