Vacation rentals in Hopewell Junction

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.

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 ✨

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!

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.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Bold & Cozy Hudson Valley Getaway w/King Bed

Relax and recharge in this cozy 1BR Hudson Valley retreat, perfect for romantic weekends or work-from-home escapes. Every detail has been thoughtfully curated for your comfort & convenience. Enjoy fast Wi-Fi, a king bed, and a fully equipped coffee station with an espresso machine and French press. Relax on the patio by the fire and catch the sunset. Just minutes from Main Street in Fishkill and a short drive to the Beacon or New Hamburg train stations.

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain, next to massive forest preserve. 90 min from NYC but feels like you're way upstate. 130+ 5-star reviews! Cozy deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + twin-size mattress day bed on the porch. Fast WiFi. Fire pit and stacks of cut wood. Plus waterfall area with meditation pier (but waterfall only active Apr-Jun) 5 miles from Beacon restaurants & Cold Spring hiking trails.

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

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!

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

Modern cottage with Hudson River view

Relax and enjoy your stay in a bright, modern cottage with windows overlooking the river and a wraparound deck. Whether you are looking to relax along the river, explore Hyde Park historic properties or discover the incredible natural beauty of the Hudson Valley, this cottage is an ideal escape.