Holiday rentals in Hopewell Junction

Dutchess Chalet - Hudson Valley Home w/ Hot Tub

Welcome to the Dutchess Chalet - a modern chalet in the Hudson Valley. Right off the Taconic parkway, this stylish home is quiet, spacious and set back on an acre of land on a friendly dead-end street. Whether you’re grilling, gazing at the stars in the hot tub, or just want to roast marshmallows around a fire pit - this is your home away from home. So close to gems like Fishkill Farms, Thunder Ridge, hiking or exploring popular local towns including Beacon, Rhinebeck and New Paltz. Book today ✨

3000 sq ft Poughkeepsie home with chef's kitchen

A wonderful home for a couple's retreat or a family fun getaway. There's even a striped basketball court outside for the round ball players. And for the chefs, cooks or even the hash slingers, there's a beautifully laid out voluminous kitchen to prepare everyone's favorite dishes. Our spacious home located on the outskirts of the town of Poughkeepsie offers a centrally located base to the heart of the Hudson Valley, which has become one of the most sought after venues to visit in the Northeast.

Hudson Valley Suite Home Cinema, Fireplace, Gazebo

Escape to your large private Garden-Level Suite! Enjoy AN ENTIRE LOWER FLOOR featuring a luxury home cinema, full kitchen, and a King master with its own fireplace. Work remotely at 2 desks or relax in the sunroom and outdoor gazebo. A private entrance ensures seclusion. Located in Fishkill near hiking and Beacon. Hosts live upstairs but respect your privacy and often leave. The perfect high-end getaway for families or remote workers looking for fun and comfort in the heart of the Hudson Valley!

Private ground floor guest suite in Hudson Valley

Guest favorite/newly renovated/private, ground floor guest suite. Br/full bath/large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen. Car suggested.

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

Heated Pool w/ Cabanas, Elevated Hot Tub & Gym

The main attractions of this home are the large heated pool, elevated hot tub, deck & two pool-side lounge cabanas nestled in the large backyard. The house features 4 proper bdrms, 4 full baths, 2 offices & 3 living room areas (which can be converted to more sleeping) across three floors. Located in the Hudson Valley just an hour north of Manhattan, this escape offers the opportunity to get a family or group of friends together to enjoy the outdoors in a spacious and warm living environment.

BIG RED the Bus at Menlo Pond

You'll love this unique and romantic escape. BIG RED with its 100% off grid capabilities, has travelled the country, giving the owner the great opportunity to explore the US. It's now tucked away, parked and here at Menlo Pond waiting for you to experience and enjoy the comfort of all it has to offer: *Queen size bed *Large couch *Full bath *Full stove/oven *Air conditioning *Large sink *concrete countertop *Butcher Block *outside picnic table, Barbque and small fire pit

La Casita - Home Away From Home.

✨ Discover Serenity at La Casita 🏠 — Your Hudson Valley Escape ✨ Cozy 3-bedroom, 1.5-bath retreat near Dutchess, Marist 🦊 University, Vassar, and the Culinary Institute of America 🧑‍🍳, it’s ideal for visits or getaways. Enjoy nearby wineries 🍷, orchards 🍎, farm markets, and hiking trails 🥾, or simply unwind and soak in the beauty of Hudson Valley’s seasons 🌻☀️🍁⛄️. Need anything specific? We’re happy to help make your stay perfect!

The GlassHouse: Hudson Valley Tiny Home w/Firepit

The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

Ideal for students and those who travel for work.

It is essentially a furnish one bedroom apt with its own bath and kitchen and its own entrance. We will accommodate the guest depending on their privacy and needs within limits. Our cozy living room features a versatile L-shaped layout with two single daybeds. It serves as a comfortable sectional lounge by day and provides two separate sleeping spaces at night.

Wabi-Sabi Zen Den | Tatami Oasis w/ Soaking Tub

Escape to YOIN 余韻·宅, a serene Japanese-inspired retreat on 2 private acres in Hopewell Junction, NY. Just 90 minutes from NYC, this minimalist sanctuary is designed for meditation, reflection, and renewal. With tatami mats, a zen meditation hall, and an onsen-style soaking tub, YOIN offers the perfect mindful escape from the city’s rush.

Private, spacious apartment

Relax at our peaceful and centrally-located home. Private one bedroom walk-out apartment with full kitchen. Only minutes away from Main Street Fishkill and Beacon. Sleeps 4 comfortably with a full size bed in the private bedroom and a queen size pull out couch in the living space.