Nice to meet you!
It's Jared & Stacey, your host.
Welcome to your luxurious Hudson Valley escape! Nestled in the heart of the historic Village of Montgomery, this stunning, newer build, 5-bedroom, 4.5-bathroom home offers the perfect blend of modern comfort and small-town charm. Lots of space, privacy, and 2 full kitchens. Whether you're planning a family reunion, a getaway with friends, a wedding, or a home base for exploring the Hudson Valley, our spacious retreat at 37 Wallkill Ave provides everything you need for an unforgettable stay.
Why Groups Love This Home
Most vacation rentals force large groups into a single shared space. This home was designed differently. Two families can share a holiday without living on top of each other. A group of friends can split up after dinner and enjoy their own living rooms. Grandparents can have their own quiet suite while the kids have the run of the other side. And when it's time to gather — for a meal, a toast, or just to enjoy the evening air — the patio and deck effortlessly bring everyone back together.
The Wallkill River Retreat isn't just a place to stay. It's the reason the trip works for everyone.
We can't wait to host you.
The Space
Your Private Hudson Valley Compound — Two Homes in One
Welcome to the Wallkill River Retreat, a beautifully renovated 5-bedroom, 4.5-bathroom home uniquely designed as two fully independent living spaces under one roof. Located in the heart of the historic Village of Montgomery, this one-of-a-kind property is the ultimate getaway for multi-family vacations, group trips, or anyone who loves traveling together while still having their own private space to retreat to at the end of the day.
Think of it as booking two vacation homes that happen to share a gorgeous outdoor patio and deck — all the togetherness you want, with all the privacy you need.
Two Complete Living Spaces, Two Full Kitchens
What makes this property truly special is its layout. Each side of the home functions as its own self-contained apartment, complete with its own full kitchen, living area, bedrooms, and bathrooms. There's no fighting over the coffee maker, no waiting in line for the shower, and no compromising on what to watch after dinner.
Space One features an expansive open-concept living area anchored by a plush, oversized velvet sofa, a dining table for the whole crew, and a stunning modern kitchen with white cabinetry, sleek dark countertops, stainless steel appliances, and a large center island with bar seating for four. It's the kind of kitchen that makes you actually want to cook on vacation — and we've stocked it with everything from a premium knife set and blender to a fully loaded spice rack so you can.
Space Two offers its own equally well-appointed full kitchen and comfortable living area, giving the second group complete independence to set their own schedule, cook their own meals, and enjoy their own downtime without missing a beat.
Two Master Suites with Private En-Suite Bathrooms
Each space includes its own luxurious master suite with an attached full bathroom, so both couples or families enjoy the same level of comfort and privacy. The bedrooms feature plush beds dressed in crisp white linens, warm wood accents, and serene, modern decor that makes it easy to unwind after a day of exploring. The spa-like en-suite bathrooms are finished with modern fixtures and stocked with fluffy white towels and all the essentials.
The additional bedrooms offer flexible sleeping arrangements — including rooms with twin beds that are perfect for kids, teens, or single travelers — bringing the total to 5 bedrooms and 4.5 baths across the property. A well-organized closet with extra linens, hangers, and storage means everyone can settle in and feel right at home.
Come Together on the Patio & Deck
Here's where the magic happens. While each space offers complete privacy indoors, the shared covered patio and upper-level deck are where your group comes together. The patio is strung with charming bistro lights, creating the perfect atmosphere for evening cocktails, barbecues, or long conversations that stretch well past sunset. The spacious deck above offers additional outdoor seating and views of the surrounding neighborhood. It's the best of both worlds — retreat to your own space when you need a quiet moment, then step outside and everyone's together again.
Neighborhood Must-Sees
Steps from the Heart of the Village
One of the best things about this property is its unbeatable location. You're just steps from the walkable, tree-lined streets of the Village of Montgomery — a charming Hudson Valley gem filled with local restaurants, cafes, and shops. Leave the car parked and stroll to favorites like The Table, Iron Cafe, or the Borland House Inn & Brunch House, all on nearby Clinton Street. Spend an afternoon browsing the village's antique shops and boutiques, or take a peaceful walk along the scenic Wallkill River.
Your Home Base for Hudson Valley Adventures
Despite the peaceful, small-town setting, you're perfectly positioned to explore everything Orange County and the Hudson Valley have to offer:
Getting Around
Parking in front of and 2 dedicated spots in the back. Please don't block the driveway.
Property type
House
Room Type
Entire home
Allowed guests
13 Members
Bedrooms
6 Bedroom
Beds
8 Beds
Bathrooms
4.5 / Private
Smoke Detector
Carbon monoxide detector
First-aid kit
Fire Extinguisher
Surveillance on property
Exterior lightning
Deadbolt lock
1 King
1 King
1 King
1 King
2 Single
2 Single
Montgomery, New York, United States
Hi!
Stacey and I have both grown up in the truth and lived in NY for the past several years. We have been married since 2006 and have 2 awesome Maltese pups. We volunteer for LDC and SMPW and really enjoy living close to Bethel, NY, and all the friends here.
We love sharing a good meal, enjoying plenty of laughter, traveling, and getting to know brothers and sisters from around the world.
As hosts, we are happy to be as involved or as hands-off as you prefer. We live nearby and are available to assist in any way needed to help make your stay comfortable and enjoyable.
We look forward to welcoming you!
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