Holiday houses in Pleasant Valley

Be our guest at The Nest!

Your Hudson Valley hideaway awaits at “The Nest”! Located only minutes from the Taconic, a short drive to Millbrook, Rhinebeck, & historic Hyde Park. 8 minutes to Baird Golf course. Conveniently located only about 20 mins from Vassar College, Marist, the Culinary Institute, Walkway Over the Hudson, & Barton Orchards. 30 minutes to Red Hook & Beacon. The property offers beautiful trees & plenty of privacy. It’s a perfect retreat to get away and enjoy all that the scenic Hudson Valley has to offer

Family · Value · Condition

Large, private apartment in scenic Hudson Valley

We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Family · Value · Parks

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.

Location · Value · Layout

Cosmic Hollow

Welcome to Cosmic Hollow, a space for adventure and retreat in the Hudson Valley. Up a private driveway, Cosmic Hollow is surrounded by a serene 32 acre forest that make it a destination for all seasons. The space is complete with a 100" projector by the two-story fireplace. The loft upstairs offers a library/yoga space. All three bedrooms including the primary suite which boasts its own sliding door, are on the first floor and have forest views! Can’t wait to have you at our special hideaway.

Family · Value · Barbecue

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Family · Location · Parks

Boulder Tree House

Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee 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 an exciting, romantic, unique experience but can accommodate a 3rd person.

Location · Family · Laundry

Hidden Charm in Hudson Valley

Welcome to your perfect getaway! Nestled on a sprawling 30 acre property in Dutchess County, our spacious home offers and unparalleled blend of comfort, tranquility, and natural beauty. Whether you're looking to relax and unwind or explore the nearby sights, our home provides the perfect base for your stay. Book now to experience the ultimate in spacious comfort and privacy! No one under the age of 25 may book. Please verify minimum age requirement with owner when sending booking request.

Value · Location · Cleanliness

Home in Pleasant Valley

Welcome to our Stunning Home in the Hudson Valley! Nestled on 7,5 acres, this home is the perfect place to unwind. Featuring 5 spacious bedrooms and 2,5 bathrooms, a pool room and even a gym! Vaulted ceilings, 2 fireplaces, expansive decking overlooks private yard with views. Lovely Gazebo, great for entertaining and perfect for all seasons The beautiful Hudson Valley offers vineyards, parks, walking trails/Rail Trail, antique shops, cozy cafes and Culinary grade restaurants.

Location · Family · Hospitality

VIEWS on Hudson River / Luxury Modern Home

Come stay on the HUDSON RIVER WATERFRONT Bluff. It is one of the most magical, luxurious experiences in all of NY. The views are insane! It's literally the perfect getaway with a major *WOW* factor - if you're wanting something very, very special. :) You'll have complete access to my gorgeous, modern, designer, peaceful mid-century home and deck. This is a luxury escape. The central location positions you near everything in the Hudson Valley. Just 2 hours north of NYC.

Location · Family · Hospitality

High Meadows | Modern Farmhouse, Pool, 13 acres

Relax and unwind in a private upstate retreat with stunning meadow views set amongst 13 acres in historic Dutchess County. Just a 2 hour drive or train ride from NYC will bring you to a refuge of rejuvenation in the country and serve as your centrally located hub to explore the nearby towns, enjoy the best shopping and culinary destinations and embrace the natural beauty of the Hudson Valley. Come find your peace while fully enjoying all that the region has to offer.

Location · Family · Nearby

Secluded Mountaintop Getaway near Poughkeepsie

Featured in the Hudson Valley Style Magazine, this Modern Rustic Mountain Getaway is a unique option for accommodations when exploring the Hudson Valley/Taconic region. The secluded getaway is nestled on top of a steep hill and offers stunning views of the surrounding area. Kick back and relax in this calm, stylish space with an amazing outdoor deck or use it as a basecamp for exploring local hiking trails, wineries, distilleries, restaurants, and farms.

Family · Value · Condition

Cardinal Cottage

Cardinal Cottage offers the best of both worlds- a charming retreat nestled in the heart of Hyde Park. Perfectly located, it's your gateway to historic landmarks, top rated dining, scenic hiking trails, and all the unique attractions the surrounding has to offer. Just a 2-hour drive or train ride from NYC, this cozy cottage is the ideal escape to relax, recharge and unwind in comfort.

Location · Family · Quiet