Woodstock, NY Vacation Rentals

Our Favorite Vacation Rentals in Woodstock

  • Tentrr - Shady Knolls
     Country House
    Booking.com
    From
    $144
  • Woodstock Cottage: walk to Town
    Excellent2br Cottage
    HolidayLettings
    From
    $408
  • Tentrr – Highwoods
     Country House
    Booking.com
    From
    $138
  • Margaret's Cottage in Woodstock Village
    Excellent2br Country House
    HolidayLettings
    From
    $192
  • Tentrr - Stonecutters Ledge
     Country House
    Booking.com
    From
    $115
  • New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $870
  • Tentrr - Camp AnuLyfe
     Country House
    Booking.com
    From
    $111
  • Marigold cabin by the stream - Heart of Woodstock with Hot Tub & Fireplace
    GoodCottage
    Flipkey
    From
    $380

Check prices for these upcoming dates

Woodstock Vacation Rentals with a Pool

  • chezbevet-country cabin retreat
    ExcellentHome/Apartment
    Airbnb
    From
    $158
  • Woodstock Retreat with Heated Saline Pool
    Excellent3br Home/Apartment
    Airbnb
    From
    $494
  • Family-Friendly 4BR House w/Pool and Hot Tub
    Excellent4br Home/Apartment
    Airbnb
    From
    $678
  • Woodstock Pool/streamEclectic Family/Dog friendly
    Excellent4br Home/Apartment
    Airbnb
    From
    $452

Woodstock Vacation Rentals with Wi-Fi

  • Church Des Artistes
    Excellent5br Country House
    Booking.com
    From
    $204
  • Dutch Touch Woodstock Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $167
  • Teahouse Cottage by the River
    GoodHome/Apartment
    Airbnb
    From
    $206
  • Maverick House Garden Studio Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $112

Woodstock Pet-Friendly Vacation Rentals

  • Tentrr - Yankeetown Pond Peace of Mind
     Home/Apartment
    HolidayLettings
    From
    $198
  • Updated/Pet-Friendly Cabin By Hikes and Woodstock!
     2br Cottage
    HolidayLettings
    From
    $266
  • Secluded, Luxury Home with Hot Tub
    Excellent2br Home/Apartment
    Flipkey
    From
    $340
  • Woodstock Hillside House With Unparalleled Views!
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $811

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

Most expensive
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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
93 º44
6
81 º28
3
69 º6
8
63 º13
4
62 º-14
3
76 º7
4
60 º16
2
74 º22
4
90 º38
3
94 º46
4
94 º51
7
93 º55
9
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Woodstock. The hottest month in Woodstock is July, when temperatures peak at 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 love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — 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

Vacation Rentals in Woodstock

Browse accommodations from all your favorite providers including Airbnb, Bed and Breakfast, Hostelworld and more at AllTheRooms.com. Woodstock has 558 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. If you are wanting to keep costs down, the cheapest place to stay in Woodstock comes in at $20 a night. A typical rental in Woodstock costs on average $251 a night.

Those looking to get some work finished during their trip to Woodstock can pick from 415 places to stay that provide WiFi. We have 42 accommodations that include a breakfast included. Fitness addicts can get a workout in during their stay by choosing from 12 accommodations that have gyms. If you are driving to Woodstock, you'll want to pick from 406 places to stay that provide parking. 50 places to stay have a a pool or jacuzzi

AllTheRooms has 186 pet-friendly places to stay in Woodstock, so if you're traveling with your pet you won't have any trouble.

454 of the places to stay in Woodstock have been reviewed by previous guests. They rated 84% as excellent or good. You can instantly book any of 212 places to stay right now.

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