The Maple Overlook
The Best Upstate New York Vacation Rental for Groups Near NYC
A private 23-acre estate in Westtown, NY. Exclusively yours.No shared spaces, no other guests, no schedule but your own.
An Upstate New Escape Unlike Anything Near the City
Most upstate New York vacation rentals give you a house. The Maple Overlook gives you an estate.
Set on 23 private acres in Westtown, NY, this property sits in the heart of the Hudson Valley region, surrounded by rolling farmland, local wineries, and the natural beauty of the Catskill Mountains.
When your group arrives, the gate closes and the entire property becomes yours.. No hotel lobby. No shared outdoor pool. No checkout time that cuts the morning short. Just space, privacy, and time that finally feels like your own.
This is the kind of upstate New York weekend getaway people remember long after they leave, where kids are still playing in the barn at midnight, the fire is still going, and no one is ready to go home on Sunday morning.
An Upstate New Escape Unlike Anything Near the City
Intimate Weddings & Celebrations
A private ceremony lawn overlooking the valley. . restored timber-frame barn glowing with string lights for dinner and dancing. Your entire group staying on-site together—no split hotels, no logistics, no stress.
Up to 30 guests for seated dinners with full estate exclusivity for the entire weekend.
Corporate Retreats & Team Offsites
Close enough to NYC that no one needs to fly. Far enough from the city that everyone actually disconnects. Easy access from Grand Central Station via the Port Jervis Metro-North line.
Leadership teams and founders choose The Maple Overlook because a private estate with a professional kitchen, barn space, and 23 acres of privacy creates a far better environment for thinking, planning, and connection than any hotel conference room.
Family Gatherings & Friend Groups
Multi-generational families. Milestone birthdays. Groups that want real connection without feeling crowded.
Five en-suite bedrooms, a barn apartment, heated pool, barrel sauna, padel court, fire pit, and open land in every direction.
Weekend Buyouts
No strangers. No shared amenities. No compromises. A private outdoor pool. A sauna. A padel court. A chef’s kitchen that gets used all weekend. A fire pit that stays going late into the night. Just your group—and 23 acres completely to yourselves. Limited weekend availability, especially during peak seasons.
What’s included in your stay
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What’s Included in Your Stay
The Main House
5 en-suite bedrooms · Chef’s kitchen with dual professional ovens · Large marble island · Wraparound porch with sweeping valley views
The Red Barn
Timber-frame event and recreation space · Private barn apartment (sleeps 2)
The Grounds:
- Heated outdoor pool with loungers
- Private barrel sauna
- Padel court with equipment
- Fire pit circle for evening gatherings
- Ceremony lawn with Catskill Mountain backdrop
- Stone terraces, gardens, seasonal blooms
- Parking for 14 + 2 garage bays
Sleeps 12 · Up to 30 for dinner · Up to 50 for receptions
Inquire for private bookings
Email Me: info@themapleoverlook.com
Marte’s home was truly incredible! Not only was the property stunning, the house itself was very thoughtfully architected and designed down to every little detail. I’ve stayed at a dozen home rentals, and this one was by far the coziest and best equipped for a very comfortable stay. My large family (ranging from 5-90 years old) had private spaces for each ourselves, yet there was no shortage of common areas for all of us to gather. Marte and her team were extremely communicative and helpful whenever we needed something. She also proactively provided local recommendations for things to do/see/eat in the area. The highlight of my family’s stay was sledding in the backyard (the view + hilly terrain was perfect) and the game room (our kids had a blast!). If you’re looking for a place to gather with family or a group of friends, this is seriously a property that will not disappoint for groups of all ages. Marte and her team are incredible and our stay is one we will never forget!
Allison Airbnb Jan ’26
This is a great spot for a family photoshoot, maternity photos, or even creating the perfect backdrop for wedding photos. The unique architecture and scenic views make it a favorite place for photographers seeking the best locations near NYC. The brick buildings in nearby Warwick, NY, add a touch of historic charm, offering a beautiful spot for both candid and posed shots.
Kalibri (Photographer)
Marte’s house and accompanying property are truly extraordinary! We travel frequently and have stayed at many rental properties and can say without hesitation that this is the most exquisite. As former Airbnb Superhosts, we are keenly aware of what it takes to provide a stellar guest experience and Marte delivered!Her design choices, attention to detail, and thoughtful touches are special and noteworthy! The views from all angles of the home are simply breathtaking. From the second you ride up the dramatic tree lined driveway, you will realize that you will be in for a treat!
Edward Airbnb Sept ’25CEO
We had the most incredible stay and cannot recommend this home enough. The house was more than big enough for 13 people across three blended families, and we never once felt crowded. The property truly felt like a retreat. The kids were obsessed with the game barn and had endless activities to keep them happy and entertained. The adults loved the barrel sauna, the pickleball courts, and the peaceful setting. Having horseback riding nearby was such a special bonus and made the whole experience feel even more memorable.
Every detail of the house was beautiful. The beds were unbelievably comfortable, which made it easy to fully relax and sleep well. The primary bedroom suite was absolutely stunning and felt like a luxury hotel. Every room having its own gorgeous en suite bathroom was such a thoughtful touch and made traveling with a big group so easy.
It was spacious, well designed, relaxing, and ideal for families and groups. We are already talking about when we can come back!
Heather Airbnb Dec ’25CEO
This was an incredible location for old friends to get back together! We had six couples and 5 children under 3, and there was plenty of space for all. An incredible kitchen and grill set up made all the meals easy, and it was fully stocked with all the kitchen items you may need. The pool was a huge hit, and we appreciated all the floats! The padel court was great, and starting the day in the sauna was amazing. Marte and her cohosts were great communicators and responded quickly to questions. The property had everything you need, come with food for your trip and you won’t need to leave at all! 10/10 house, would definitely come back for another big group trip!
Ian Airbnb Sept ’25CEO
Meet the Founder
Owner of the Maple Overlook. Mirte has a love for homes and truly remarkable design. She purchased the property one year ago and since than has been transforming the property to a true Luxury Estate! Padel within 90 min from NY with a heated outdoor pool and sauna. This is the perfect family or friends getaway from New York City.