Family-friendly holiday rentals in Dutchess County

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. 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.

Private ground floor guest suite in Hudson Valley

Newly renovated private, ground floor guest suite returning for 2025 rentals! 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.

Historic 1 BR Family Home Near Buttermilk Falls

This historic upstate New York family home was lovingly restored by 4th generation owners. Once a 1790 Stagecoach Stop, this 1 BR home is now the perfect stay for guests visiting Buttermilk Falls Resort & Spa, coming for a wedding in the Hudson Valley, or exploring local agritourism. Enjoy our large kitchen and sitting area, 180-degree sunroom, and newly-renovated bathroom. Our home is a duplex that sits on 5 wooded acres, and the other side of the home is also available for rent on AirBnB.

Top Floor 2BR - Just Renovated!

This 2BR apartment is the entire top floor of an 1870 brick house. Extensively renovated in 2021 - all new kitchen, major updates to the bathroom, furniture and decor throughout. Directly behind the house is Fishkill Creek and abandoned railway tracks (you can walk to Main St on them in 10 minutes). The property has a separate patio & treetop hot tub with view of the creek and Mt Beacon for private additional rental (pending availability). Inquire for details. [Permit: 2024-0027-STR]

Romantic Sunset View, horse country, nature & WiFi

Luxurious private suite with stunning 50-mile Hudson River Valley sunset views! Horse country, ideal for horse and nature lovers and 200+bird species. Private entrance, kitchen, bathroom, HEPA filters, 500Mbps WiFi, 55” 4K TV. Enjoy a private pond for picnics, luxurious cushioned chaise lounges, another private deck and dock, table & chairs, firepit, badminton on 25 acres. Stargaze & delight in fireflies! Relax on the deck with crisp mountain air. Near picturesque towns.

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

The Farmhouse

The Farmhouse is a carefully restored home built in 1828. The property has a 4 generation history in the Ryan family. The ultimate retreat for any family, or just a couple that wants a private country estate setting. The home has modern amenities with a true rustic original feel and a view from every window. There have been many memories created on the property and we hope there will be many more for the travelers coming to the Hudson Valley.

Charming Lakefront Escape with Views

A year-round waterfront home with gorgeous unobstructed views of Whaley lake provides the perfect escape for a long weekend or vacation. Enjoy swimming and lake activities via private direct lake access. Spacious boathouse deck for entertaining or sunbathing. Cozy up to a two-story stone fireplace while enjoying the fall and winter colors.

Clausterhaus

The "cozy cottage" with a rustic feel but all the amenities of a fine hotel- exposed beams-goose down sofas and chairs- old fashioned gas burning stove to keep you warm in the cold winter months. *Please take note that we are not currently serving breakfast due to the pandemic but hope to resume when it is safe to do so.