Woodstock, NY Vacation Rentals

Our Favorite Vacation Rentals in Woodstock

  • Tentrr – Highwoods
     Country House
    Booking.com
    From
    $150
  • Woodstock Cottage: walk to Town
    Excellent2br Cottage
    HolidayLettings
    From
    $408
  • Romantic, Magical Cottage in Catskills nr Woodstock
     Country House
    Booking.com
    From
    $265
  • Marigold cabin by the stream - Heart of Woodstock with Hot Tub & Fireplace
    GoodCottage
    Flipkey
    From
    $380
  • Sioux Tipi on Chloes Lake
     Glamping
    Booking.com
    From
    $160
  • Peaceful Woodstock Retreat - Restored Barn
     3br Farmhouse
    HolidayLettings
    From
    $624
  • Mink Hollow Lodge
     Country House
    Booking.com
    From
    $1,176
  • Charming Artist's Cottage
    Excellent2br Cottage
    Flipkey
    From
    $258

Check prices for these upcoming dates

Woodstock Vacation Rentals with a Pool

  • chezbevet-country cabin retreat
    ExcellentHome/Apartment
    Airbnb
    From
    $158
  • Private guest cottage on 5 acres
    ExcellentHome/Apartment
    Airbnb
    From
    $186
  • Fontyne Kill Farm
    Excellent2br Home/Apartment
    Airbnb
    From
    $328
  • Gather Friends at the Tranquil Mountain Mod in Woodstock
    Excellent5br Home/Apartment
    Airbnb
    From
    $607

Woodstock Vacation Rentals with Wi-Fi

  • Church Des Artistes
    Good5br Country House
    Booking.com
    From
    $204
  • Rocket Room - Rock Stars Only
    ExcellentHome/Apartment
    Airbnb
    From
    $137
  • Teahouse Cottage by the River
    GoodHome/Apartment
    Airbnb
    From
    $251
  • In town, 1840s Converted Barn with Backyard Brook
    Excellent4br Farmhouse
    Airbnb
    From
    $314

Woodstock Pet-Friendly Vacation Rentals

  • Updated/Pet-Friendly Cabin By Hikes and Woodstock!
     2br Cottage
    HolidayLettings
    From
    $319
  • Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $954
  • Romantic Country Barn By the Stream
    Excellent2br Farmhouse
    Flipkey
    From
    $317
  • charming woodstock cottage with outdoor hottub
    Excellent2br Cottage
    HolidayLettings
    From
    $238

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
69°
8
63° 13°
4
62° -14°
3
76°
4
60° 16°
2
74° 22°
4
90° 38°
3
94° 46°
4
94° 51°
7
93° 55°
9
93° 44°
6
81° 28°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Woodstock. The warmest months in Woodstock are July and June, when temperatures reach 94 ˚F. The coolest month is December, when temperatures drop to -14 ˚F. The wettest month in Woodstock is May with 8.52 inches of rain, while the driest month is October with 2.23 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

Vacation Rentals in Woodstock

Find the perfect vacation rental for your trip at AllTheRooms.com. We compare Airbnb, Bed and Breakfast, Hostelworld and many more. We have 589 vacation rentals, hotels and other accommodation types in Woodstock ranging from cheap options to luxury places to stay. A vacation in Woodstock can be affordable - the lowest price accommodation is available at $20 a night. A typical accommodation in Woodstock costs on average $252 a night.

Those looking to get some work done during their trip to Woodstock can choose from 341 places to stay that have WiFi. 44 of our accommodations include a breakfast in the price. Choose from 6 accommodations that provide gym options, so you won't miss a single workout. If you are driving to Woodstock, you'll want to pick from 322 places to stay that provide parking. 51 places to stay have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 147 accommodations that are designated as pet-friendly.

467 accommodations in Woodstock have been reviewed; 82% are rated excellent or good. You can instantly book any of 231 places to stay right now.

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