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.

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 the idea of 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 family leads 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.

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:

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New York City is just 60–70 miles away — an easy weekend escape from the city.

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LEGOLAND New York Resort in nearby Goshen is a short drive and a must for families.

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Storm King Art Center offers world-class outdoor sculpture and stunning landscapes.

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West Point and its historic grounds are right up the road.

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Shawangunk Wine Trail and City Winery Hudson Valley are perfect for a day of tastings.

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Woodbury Common Premium Outlets are easily accessible for a day of luxury shopping.

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Local farms, orchards, and seasonal festivals round out the experience year-round.

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 bring everyone back together effortlessly.

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.