Vacation rentals in Dutchess County

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.

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.

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Lake Side Tiny House

Reconnect with nature at this unforgettable escape. Sitting on a beautiful 5 acre property, tucked back in the woods along a beautiful lake. Come stay and unwind. Plenty to explore and just be. Lake access for swimming or with paddle board, canoe, or kayak. Just ask and can be assisted with. The whole property has been curated to be a playground. Full bathroom inside unit. Brand new Mini Split heat and AC unit. Works amazing Has most kitchen amenities besides an oven. Enjoy

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.