Family-friendly holiday rentals in Germantown

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Livingston Farmhouse Escape with hot tub and sauna

Perfect rustic country getaway conveniently located near Hudson, Red Hook, Tivoli and Germantown; in the heart of a sweet hamlet. Farm stands and swimming holes abound! Our home is an open and airy 3 bedrooms; space to spread out, and a large kitchen equipped with all a cook could want. Generously sized living room with cozy fireplace and Roku TV. Sonos throughout first floor. Huge property with fire pit for s'mores and late night fun; grill, patio dining, sauna and hot tub.

The Greenhouse - Ski House by Hunter

The Hunter Greenhouse is a place to slow down, indulge in personal nostalgia, drink a glass (or two) of wine, and let your mind disconnect and wander. A place designed for friends and family. For good food and good conversation. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking • we look forward to having you here!

Cozy Modern Farmhouse, a close walk to Warren!

Welcome to This Old Hudson! This spacious, light-filled rental has been tastefully renovated by Zio and Sons with vintage charm and artful details. The luxuriant, timeless design combines comfort, convenience, and elegance. A quick walk to Warren Street offers the finest eateries, art galleries, and antique stores the valley has to offer. We take pride in our exceptional hospitality with this authentic rental experience

Stargazer Upstate glamping at Gatherwild Ranch

Welcome to Gatherwild Ranch, an Outdoor Inn, home to 8 beautiful and unique accommodations spread out on the rolling hills of a former apple orchard. As featured in The New York Times, we provide a luxurious and fun farmstead experience in the heart of the Hudson Valley, and offer a place to reconnect with nature while being close to all the best happenings of Upstate.

Byrdcliffe Artist Studio (27.1-1-70)

Historic Byrdcliffe Artist's Studio ... is a classic cabin in the woods where theater companies were launched, cartoon characters drawn, and famous books written. Quiet & inspirational, perfect for artists, couples, close friends, and small families. A place to breathe fresh air & see the stars. Everyone is welcome!

Architectural wonder in the woods

Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4!

Cozy cabin in the Hudson Valley!

Our cool, cozy rustic cabin sits on 4+ acres with a creek bordering the back field. When you're ready to venture out, Rhinebeck, Hudson and Tivoli are just a short drive away. Three bedrooms, wood burning stove, cabin-y furnishings for a laid-back stay. The whole house is yours to enjoy.