Holiday rentals in Maybrook

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 4 people.

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Rustic Ranch w/ Fire Pit, Trails & Grazing Horses

Escape the city and wake to the sound of grazing horses. Nestled on a 50-acre equestrian property, the Carriage House blends cozy charm with eclectic design and wide-open skies. Sip morning coffee with views of the Moodna Viaduct, then hike our private trails or explore Storm King Art Center. Unwind by the fire pit, or book a hands-on horse experience with our gentle herd. Nearby: wineries, hiking, farm markets,& MetroNorth (NYC in ~90 mins) Ideal for couples, small families, or solo retreat

Serene Hudson Valley Escape Hottub/Pool/King Suite

Welcome to our comfortable haven, perfectly situated to offer the best of the Hudson Valley! This centrally-located gem ensures closeness to the attractions the area has to offer. Explore Legoland, Angry Orchard, fine dining & shopping in historic Downtown. Nature enthusiasts will love hiking the nearby mountain ranges. Central to WT Farms & tours. See the MET & NYC offerings with the Beacon train. Enjoy the perfect blend of relaxation, adventure, & convenience. We look forward to hosting you!

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

Treehouse-Inspired Cabin Escape w/ Theatre & Gym

Welcome to your getaway in Montgomery, where cozy cabin charm meets modern comfort. This 3-bedroom, 3.5-bath home offers a treehouse vibe surrounded by nature. Enjoy a private pool, theatre room, game room, gym and fireplace. Spacious living areas and a full kitchen make it perfect for groups or families. Relax, recharge, and make unforgettable memories in this peaceful yet conveniently located getaway. We're also conveniently located 20 minutes away from hiking trails and skiing mountains!

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

The B House

The “B” house, constructed in the 19th century, underwent renovations and modernizations to accommodate contemporary living standards while preserving its original architectural charm. The house boasts magnificent beams that span the entire interior, creating a sense of grandeur. Additionally, newly renovated appliances and updated bathrooms have been installed throughout the property. The kitchen features an expansive open space, elegant countertops, cooking essentials are top-notch.

16taft

16taft is a newly built loft set in the quaint Village of Mongomery in the Hudson Valley. The upper level of a barn-style building, it is located on a quiet street walking distance to cafes, restaurants and shops. With a 1,000 sf open floor plan including vaulted ceilings with exposed beams, barn lights and wide board pine flooring it has old charm for a new building. Outdoors, an impressive sunken circular fieldstone patio with BREEO fire pit is available for your enjoyment.

Cozy Lakeside Cottage Escape

Relax with the whole family at this peaceful place to stay with over 200 feet of lakefront access. Lovely two bedroom cottage with fireplace, pullout sectional sofa with Queen sized bed, full wait in kitchen and sunroom with office space for remote working. Huge yard right in the lake with private dock and lake access. Enjoy fishing and boating with the family. Conveniently located near Lego Land and downtown Newburgh for beautiful dining along the great Hudson River.

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House