Disconnect to Reconnect in Woodstock
Escape to Woodstock Highlands, a cozy family retreat in the heart of the Hudson Valley, just ~2 hours from Manhattan. This modern farmhouse has everything you need to kick back, spend quality time with your loved ones, and enjoy the beauty of the outdoors.
- 10 Guests
- 4 Bedrooms
- 7 Beds
- 2.5 Bathrooms
Step inside Woodstock Highlands, where modern style meets farmhouse charm. This thoughtfully designed 2,500 sq. ft. retreat features four spacious bedrooms, a fully equipped kitchen, and cozy spaces perfect for gathering with family. Spend your mornings sipping coffee on the four-season porch, afternoons by the heated saltwater pool, and evenings around the fire pit under the stars.
Whether you’re cooking meals together, exploring nearby Woodstock, or just enjoying quiet time in the beautiful backyard, this home is designed to make every moment special.
Take a virtual tour of our home and explore every space before you arrive. From the cozy living areas to the private heated pool, see what makes Woodstock Highlands the perfect retreat for your family getaway.
We’ve created a space where families can truly relax and have fun. The house is stocked with all the essentials you need (especially if you’re traveling with kids), plus plenty of entertainment options for everyone.
Inside, you’ll find:
- Family Comfort: Spacious bedrooms with extra pillows, blankets, and room-darkening shades for a great night’s sleep.
- Well-Equipped Kitchen: Everything you need for family meals, including all-clad cookware, a dutch oven, Henkel knives, Corelle dinnerware, and even a rice maker and blender for your convenience.
- Kid-Friendly Essentials: Pack 'n play, high chair, children’s dinnerware, and a baby bath to make traveling with little ones easy.
- Year-Round Relaxation: A cozy indoor fireplace and a four-season porch for quiet moments, no matter the weather.
- Seamless Stays: Thoughtful touches like a full-size washer and dryer, luggage drop-off, and self check-in ensure a hassle-free experience from arrival to departure.
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We’ve packed in plenty of ways to keep everyone entertained. Whether you’re into games, outdoor fun, or just kicking back, you’ll find something to enjoy here.
- Game room with ping pong and billiard tables
- Outdoor treehouse for the kids
- Fire pit perfect for s'mores
- A cozy indoor fireplace for chilly evenings
- Hammock for lazy afternoons
- BBQ grill for outdoor cooking
- Board games for family game nights
- 55-inch HDTV with Netflix, Disney+, HBO Max, Amazon Prime Video, and Hulu
- Private outdoor pool (available seasonally, open 24 hours, heated, with a pool cover and pool toys)
- Game room with ping pong and billiard tables
- Outdoor treehouse for the kids
- Fire pit perfect for s'mores
- A cozy indoor fireplace for chilly evenings
- Hammock for lazy afternoons
- BBQ grill for outdoor cooking
- Board games for family game nights
- 55-inch HDTV with Netflix, Disney+, HBO Max, Amazon Prime Video, and Hulu
- Private outdoor pool (available seasonally, open 24 hours, heated, with a pool cover and pool toys)
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Woodstock Highlands is perfectly situated just five minutes from the heart of Woodstock and only ~2 hours from Manhattan, making it an easy escape from the city.
Explore local dining at Oriole 9 or Yum Yum Noodle Bar, pick up fresh groceries at Sunflower Market, and enjoy small-town vibes at artisan shops and cozy cafes.
Whether you’re after nature, great food, or relaxation, it’s all just around the corner. For more ideas on where to eat, shop, and explore, check out our full list of recommendations clicking on the button below.
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About Us
I’m Anthony, and I’ll be managing your stay at Woodstock Highlands. We’re a family of four who, like many New Yorkers, spent years dreaming about a place to escape the city’s constant buzz. In 2019, we finally found this gem in Woodstock and spent months renovating it to create the perfect balance of modern comfort and upstate charm.
We’re not trying to run a hotel here – this is our family’s second home, and we love sharing it with guests who appreciate what makes it special. Whether you’re looking to reconnect with your kids away from screens, celebrate a family milestone, or just need a change of scenery, we’ve tried to create a space that feels both exciting and comfortable.
When we’re not here, we’re probably dreaming up new improvements or gathering local recommendations to share with our guests. This house has become our favorite place to slow down and actually spend time together, and we hope it becomes that for your family too.
Have any questions or need help planning your trip? Feel free to reach out — we’re happy to help make your stay as seamless and enjoyable as possible!
What Our Guests Are Saying
See why families love their stays at Woodstock Highlands! Here’s what our guests have shared about their experiences.
Get in touch
Planning a family getaway? Have questions about the house or area? We’re pretty quick with responses and love helping guests plan their perfect stay. We know the area well and are happy to share our favorite spots and activities. Drop us a note below, and we’ll get back to you shortly with everything you need to know.
Make Time for What Matters Most
Reconnect, relax, and create memories your family will treasure forever. Book your stay at Woodstock Highlands today and start planning your perfect getaway!