Woodstock, NY Vacation Rentals

Our Favorite Vacation Rentals in Woodstock

  • Teahouse
     Country House
    Booking.com
    From
    $290
  • Margaret's Cottage in Woodstock Village
    Excellent2br Country House
    HolidayLettings
    From
    $213
  • Mink Hollow Lodge
     Country House
    Booking.com
    From
    $1,200
  • Wonderful Woodstock Garden House w large firepit!
    Excellent3br Home/Apartment
    Flipkey
    From
    $397
  • The Carriage House Loft
     5-star Country House
    Booking.com
    From
    $225
  • New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $901
  • Church Des Artistes
    Good5br Country House
    Booking.com
    From
    $163
  • Contemporary, Secluded Cabin In The Heart of Woodstock
    ExcellentCabin
    Flipkey
    From
    $325

Check prices for these upcoming dates

Woodstock Vacation Rentals with a Pool

  • COUNTRY HOME Fireplace, 1 mi. to Town, Fenced Yard
    Excellent3br Home/Apartment
    Airbnb
    From
    $494
  • chezbevet-country cabin retreat
    ExcellentHome/Apartment
    Airbnb
    From
    $158
  • Fontyne Kill Farm
    Excellent2br Home/Apartment
    Airbnb
    From
    $316
  • Zina's Cottage in Woodstock NY- river access
    ExcellentHome/Apartment
    Airbnb
    From
    $201

Woodstock Vacation Rentals with Wi-Fi

  • Dutch Touch Woodstock Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $167
  • Streamside Cottage walk to Town
    ExcellentHome/Apartment
    Airbnb
    From
    $226
  • Peaceful Escape - The Shire at Woodstock, NY
    Excellent3br Home/Apartment
    Airbnb
    From
    $598
  • Woodstock Village Green Getaway
    ExcellentHome/Apartment
    Airbnb
    From
    $316

Woodstock Pet-Friendly Vacation Rentals

  • Peaceful Woodstock Retreat - Restored Barn
     3br Farmhouse
    HolidayLettings
    From
    $566
  • Charming Artist's Cottage
    Excellent2br Cottage
    Flipkey
    From
    $258
  • Chic Retreat in Bearsville 2 m to Woodstock, Saline Pool, Fireplace and Hot tub.
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $598
  • NEW! Newly Renovated City Escape in Hudson Valley!
     2br Home/Apartment
    HolidayLettings
    From
    $313

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
59° -4°
4
61° -3°
2
72°
2
78° 20°
4
88° 40°
5
90° 41°
4
97° 56°
3
91° 48°
4
92° 38°
1
88° 30°
5
70° 15°
3
54°
4
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
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

  • — 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
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — 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 rental for your trip at AllTheRooms.com. We compare Airbnb, Priceline, Hostelworld and more. Woodstock has 510 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. If you are trying to keep costs down, the lowest priced place to stay in Woodstock is just $20 a night. In general, a place to stay in Woodstock will cost you $255 per night.

If you need to stay connected during your trip, then you can choose from over 300 accommodations in Woodstock that have WiFi. 37 places to stay include a morning meal. Choose from 6 accommodations that provide gym facilities, so you don't miss a single workout. If you're planning on arriving in Woodstock by car, be sure to choose from 296 accommodations that provide parking. 48 accommodations come with a pool or jacuzzi

AllTheRooms has 121 pet-friendly places to stay in Woodstock, so if you're traveling with your pet you won't have any trouble.

435 of our accommodations in Woodstock have been reviewed and rated. 86% are rated excellent or good. 209 accommodations allow instant booking.

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