House holiday rentals in Dutchess County

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

Contemporary Hudson Valley home

Our home is a 1970s architectural gem located in the convenient upstate NY town of Staatsburg. It has been thoughtfully modernized and designed to encourage maximum serenity and enjoyment of both the indoor and outdoor spaces. The floating staircase, huge picture windows, expansive deck and wooded outdoor space make this home perfect for an upstate getaway - while still being close to some of the major area attractions and towns. Our historic street also features 1700s homes and a farm/brewery.

Serene Waterfront Mill House, Stroll to Village

Sweet 1840 mill house on the water, nature-filled back deck yet 5 mins walk to antiquing & excellent Millbrook restaurants. Make this your base as you explore the beautiful Hudson Valley. Or relax out back & enjoy the birds & stream. Farmhouse antique shabby chic decor with king tempurepedic bed in large second floor master BR, two BRs with twin trundle beds, 1 bathroom upstairs & 1 down, A/C, ceiling fan, cozy woodstove, wifi with smart tv, eat-in kitchen, coffee/tea, plenty of free parking.

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

Welcome friends to our beloved waterfront cottage right on the Esopus Creek, in the beautiful Catskills! Whether you’re seeking a peaceful retreat, fun for the family, or a romantic escape, our 2-bedroom home is your perfect Catskills destination. With kayaks for adventures on the creek (Spring through Fall), a firepit with water views, outdoor dining with a grill, and located close to lots hiking and nearby towns, like Woodstock and Saugerties, you'll only wish you could stay here longer!

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.

Hudson Valley Farmhouse | Winery & Hiking Getaway

Tucked into the Hudson Valley, our restored 1873 farmhouse is made for slow mornings, fresh coffee, and easy weekends between hiking trails and nearby wineries 🌿 This is a private 3BR/2.5 bath first-floor unit within a shared home. Designed for a calm, quiet stay. Only registered guests are permitted on the property. Located in Marlboro near Beacon, New Paltz, Kingston West Point, Vassar, Marist, Warwick & Wallkill with a garden to enjoy and harvest fresh herbs and seasonal vegetables.

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Nature Retreat with Pond Views and Fire Pit

Nestled among the trees, this bright and serene home is off a quiet road just minutes outside the village of Rhinebeck. The house features lots of light, direct pond view, indoor fireplace, and renovated kitchen. We offer a great value while providing high-end amenities like luxury linens and towels, hybrid memory foam beds, and down pillows and comforters. This home sleeps eight (and up to ten with the two rollaway beds) and is the perfect getaway for a group trip or family stay.

Hudson River View w/ Hot Tub & Sauna near Kingston

Water views of the Hudson River from this 3 story wellness chalet style home with plenty of outdoor space. The home offers an outdoorsy feel for relaxing just outside downtown Kingston (car is needed, 5 minutes). Perfect for summer or winter and working from "Home". The home includes a sauna, hot tub, fenced backyard for your pet, 3 decks (the second-story deck is covered so if there's a thunderstorm you can still relax and enjoy the outdoors), grill, and a gas fire pit.

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.