Woodstock Highlands
Family Oasis - Minutes from Hiking & Skiing
- 10 Guests
- 4 Bedrooms
- 7 Beds
- 2.5 Bathrooms
Featured in Hudson Valley Style Magazine, this fully updated modern farmhouse is ready to host. Radiant-heated full baths, whole-house generator, PRIVATE heated saltwater pool (schedule/weather permitting), four-season porch, indoor fireplace, fully equipped kitchen, outdoor grill, etc. Basement includes ping pong and pool tables. All bedrooms and full baths upstairs. Half bath on the main floor.
Designed for Family Comfort
Escape to a home that’s made for making memories. Whether you’re starting your morning with coffee on the four-season porch, spending the afternoon by the pool, or gathering around the fire pit under the stars, every detail has been designed to bring families together.
- Spacious & Cozy Living Areas: An open-concept layout with plenty of seating, a wood-burning fireplace, and large windows that let in natural light.
- Well-Equipped Kitchen: Stocked with high-quality cookware, modern appliances, and a dining table perfect for shared meals.
- Relax Year-Round: Enjoy the private heated saltwater pool (seasonal), cozy up by the indoor fireplace, or take in the peaceful surroundings from the four-season porch.
- Entertainment for All Ages: A game room with ping pong and pool tables, board games, and a 55-inch HDTV with Netflix, Disney+, HBO Max, and more.
- Outdoor Fun: A fire pit for s’mores, a hammock for lazy afternoons, and a spacious backyard perfect for kids to run and play.
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.
Bedrooms
All four bedrooms are located upstairs, ensuring privacy and a restful night’s sleep.
Bedroom #1
Queen bed, en-suite bathroom, and scenic views.
Bedroom #2
Double bed + bunk bed, a great setup for kids or extra guests.
Bedroom #3
King bed, room-darkening shades, and plenty of closet space.
Bedroom #4
Two queen beds, offering flexibility for large families or groups.
Bathrooms
Thoughtfully designed for comfort and convenience, the bathrooms are stocked with essentials and modern amenities to make your stay effortless.
Full Bathroom 1
Full Bathroom 2
Half Bathroom
Living & Outdoor Areas
Every corner of Woodstock Highlands is designed for comfort, relaxation, and togetherness. Whether you’re unwinding in the cozy living room, sharing a meal in the spacious dining area, or soaking up nature in the beautiful outdoor spaces, there’s plenty of room to make yourself at home.
- Click on any picture to zoom in
Amenities
Kitchen
Refrigerator, microwave, freezer, dishwasher, oven, toaster, and blender.
Cooking basics (pots and pans, oil, salt and pepper)
Dishes and silverware (Bowls, chopsticks, plates, cups, etc.)
Stainless steel gas stove
Coffee maker: drip coffee maker
Wine glasses
Baking sheet
Rice maker
Barbecue utensils (Grill, charcoal, bamboo skewers/iron skewers, etc.)
Dining table
Coffee
Bedrooms & Laundry
Free washer and dryer – In unit
Essentials (Towels, bed sheets, soap, and toilet paper)
Hangers
Bed linens (Cotton linens)
Extra pillows and blankets
Room-darkening shades
Iron
Drying rack for clothing
Clothing storage: closet and dresser
Bathroom
Bathtub
Hair dryer
Cleaning products
Shampoo
Conditioner
Body soap
Hot water
Shower gel
Family
Pack ’n play/Travel crib
Children’s books and toys
High chair
Baby bath – always at the listing
Children’s dinnerware
Fireplace guards
Board games
Babysitter recommendations
Entertainment
55 inch HDTV with Netflix, Disney+, HBO Max, Amazon Prime Video, Hulu
Fast wifi – 378 Mbps
Verified by speed test. Stream 4K videos and join video calls on multiple devices.
Pool and ping pong table
Books and reading material
Outside Area
Private outdoor pool – available seasonally, open 24 hours, heated, pool cover, pool toys, saltwater
Private backyard – Not fully fenced
Fire pit
Outdoor furniture
Hammock
Outdoor dining area
BBQ grill
Heating and Cooling
Central air conditioning
Indoor fireplace: wood-burning
Portable fans
Central heating
Portable heater
Home Safety
Exterior security cameras on property (Motion Sensor)
Smoke alarm
Carbon monoxide alarm
Fire extinguisher
First aid kit
Services
Luggage dropoff allowed (For guests’ convenience when they have early arrival or late departure)
Long term stays allowed (Allow stay for 28 days or more)
Self check-in
Smart lock
Cleaning available during stay
Parking & Accessibility
Private entrance
Location
Woodstock Highlands is just five minutes from downtown Woodstock—where you’ll find farm-to-table dining, artisan shops, and cozy cafés—and only ~2 hours from Manhattan, making it the perfect escape from the city.
- Local Eats: Grab breakfast at Oriole 9 or fresh-baked bread from Bread Alone.
- Shopping & Essentials: Stock up on groceries at Sunflower Market or Hannaford.
- Outdoor Adventures: Hike scenic trails, hit the ski slopes, or explore the natural beauty of the Hudson Valley.
Looking for more recommendations? Click here to explore the full location guide
Rules & Policies
- Check-in: 4:00 PM - 10:00 PM
- Checkout: before 11:00 AM
- Self check-in with smart lock
- 10 guests maximum
- Quiet hours: 9:00 PM - 8:00 AM
- No pets
- No parties or events
- Commercial photography allowed
- No Smoking
- Please remove your shoes while indoors
Cancellation Policy
- 30 days before check-in, full refund. Get back 100% of what you paid.
- Until 7 days before check-in, partial refund. Get back 50% of every night. No refund of the credit card fees fee.
- After 7 days before check-in, No refund.
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.
Book Now
Woodstock Highlands
Make time for what matters most – relax, reconnect, and create lasting memories at Woodstock Highlands. Pick your dates, check availability, and lock in your stay.
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!