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Find Woodstock Family Hotels from $299

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Best Woodstock Family Hotels

Mountain Studio  
Escape NYC Fall🍁
Hikers SEPT/NOV 
near ski 
Sun-Th $specials
Great for families
The price is $299 per night from Oct 31 to Nov 1
4.9/5Exceptional! (28 reviews)
Families like: outdoor pool, kitchen, skiing nearby, outdoor tennis court
Amazing experience

"Ike and Carole are wonderful hosts who are extremely helpful. The house was cozy, clean and located on a beautiful setting. Perfect weekend getaway!"…"

Reviewed on Oct 21, 2020

Mountain Studio Escape NYC Fall🍁 Hikers SEPT/NOV near ski Sun-Th $specials
Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
Great for families
4.9/5Exceptional! (10 reviews)
Families like: outdoor pool, kitchen, skiing nearby, outdoor tennis court
Peaceful cottage just outside of town

"This was an excellent option for staying in Woodstock. Having booked without knowing the town we were delighted that the cottage was a a short drive and situated in a quite area with beautiful views. We particularly enjoyed the visit from deer in the mornings. Ike was incredibly helpful and knows ..."…"

Reviewed on Aug 19, 2019

Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
Hotel Dylan
3 out of 5
320 Maverick Road, Woodstock, NY
Get Rates
4.7/5Exceptional! (109 reviews)

"A really cute motel/hotel, newly renovated, comfortable bed, clean room and great staff. Loved hanging out in the lobby by the fireplace, getting a drink at the bar and playing the board games they had to borrow. Also loved the s’mores kit and fire pit outside. Less than 10 minutes drive to the center ..."…"

Reviewed on Jan 3, 2020

Hotel Dylan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where Should We Stay in Woodstock?

If you've been thinking about a trip with your kids, the relaxing destination of Woodstock is a good choice. The art scene, hiking trails, and libraries are just a few things that make this an attractive family vacation destination. Arrange a flight into Hudson, NY (HCC-Columbia County), which is located 27.2 mi (43.7 km) from the city center. Woodstock has 4 kid-friendly hotels and other accommodations.

Families on vacation have positive things to say about these accommodations:

Hotel Dylan - Offers a restaurant, free parking, and free WiFi. Guests like the comfy beds and clean rooms at this 3-star hotel.

Hikers Haven Sunset Studio #1 Woodstk FOR 13 Years. Privacy. Pool. Views - Offers in-room kitchens, an outdoor tennis court, and free WiFi. Guests like the central location at this apartment.

When Should We Visit Woodstock?

You're likely hoping for good weather for your family vacation. You can use this information to decide when to grab the kids and head to Woodstock.

  • Hottest months: July, August, June, and September, with an average temperature of 83°F
  • Coldest months: January, February, December, and March, with an average temperature of 17°F
  • Driest months: February, January, November, and December, with an average rainfall of 3.19 inches
  • Rainiest months: July, October, June, and May, with an average rainfall of 4.50 inches

What Should We See and Do in Woodstock?

While you are vacationing in Woodstock, you and the family might want to see interesting spots such as Woodstock Public Library and Opus 40. Make sure you have lots of time for activities like James Cox Gallery and Mount Tremper Arts.

Woodstock is also well-known for the:
  • Forests
  • Riverfront
  • Art
  • Mountain views

Frequently asked questions

What's Woodstock like for family-friendly vacations?
The relaxing destination of Woodstock is a good choice if you’ve been considering a getaway with your kids. The forests, hiking trails, and libraries are just a few things that make this the ideal place for a family vacation. Arrange a flight into Hudson, NY (HCC-Columbia County), which is located 26.4 mi (42.4 km) from the city center.
What's the best place to stay for a family trip to Woodstock?
Mountain Studio Escape NYC Fall🍁Hikers SEPT/NOV near ski Sun-Th $specials is an apartment with an outdoor pool and in-room kitchens, and it’s a top choice on Expedia for families. Other good options to stay with the kids include Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village and Hotel Dylan.
What's the weather like in Woodstock?
The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Woodstock are December, January, February, and March, with each month seeing an average of 9 inches of snowfall.
What's there to see and do with your family in Woodstock?
While you and your family are visiting Woodstock, you might want to check out some kid-friendly attractions such as Woodstock Public Library, Hunter Mountain, and Opus 40. Make sure you have plenty of time to take in activities in the area like Catskill Mountains and Windham Mountain Resort.

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