Holiday rentals with a kayak in Dutchess County

Magical Waterfront Escape on the Esopus Creek

Magical and creative! Get ready for the most unique and one of the most popular properties in the Hudson Valley for over 18 years. With 150 feet of frontage on the Esopus Creek in the back of the property and the rolling hills and barns of an organic farm in the front. Tranquility dominates the views seen from every vantage point of this gorgeous house located at the base of the Catskill mountains. Truly the coziest little getaway perfect to escape all the hustle and bustle of life!

Stunningly Designed Historical Icon w/ Hot Tub

Welcome to our historic & meticulously restored home, Willow Vale, situated on a quiet & idyllic country road and nestled on 700' of Shekomeko riverbank. Built in 1790, the home was once the iconic "Mon Blason" - an inn and the *first French haute cuisine restaurant* in the Hudson Valley, owned and operated by Charles Virion, the former private chef to Orson Wells, Richard Rogers (of Rogers and Hammerstein), and John and Mable Ringling (of Ringling Bros and Barnum & Bailey Circus).

Creekside Cottage

Set on the beautiful Esopus Creek, this lovely 2 BR, 2 bath home is perfect for a get-away w/family, friends or a romantic or creative retreat. It's just a 15-20 minute drive to the quaint Village of Saugerties, Kingston, Woodstock & Rhinebeck. Sit & watch the river run by on the screened porch or on the deck down by the river's edge, bbq (4 burner gas stove), play board games, take a kayak or swim in the river. Kitchen w/full amenities. Pets are not allowed unless pre-approved.

Lovely 1 bedroom apt. with free parking in Rondout

Large 1 bedroom apartment with 10 foot ceilings, located in Kingston Historic Rondout District. Queen size bed and one large futon conversation, there are large pocket doors that separate the bedroom from the living room, pool table, lots of natural light, blackout curtains , air conditioning, claw foot tub, small private patio, 60 inch wall tv, walk to the historic Rondout water front, restaurants, boat rides, trolly, art galleries, Kingston Point Beach and Hudson Brickyards.

Goose Landing Cottage by the lake with NEW Hot Tub

The cottage is a wonderful getaway for 2 people. Drive down a private road on the back side of a spring fed lake. See turtles eagles and geese. Swim or kayak from your own private dock. No motor boats allowed. The cottage is nestled back in the woods with your own private hot tub. A great place to get away, see wildlife such as deer, turkey, Canadian geese, an occasional fox. Best for a couple or a single person. Take a short stroll down a path to a wonderful spring lakefront.

BIG RED the Bus at Menlo Pond

You'll love this unique and romantic escape. BIG RED with its 100% off grid capabilities, has travelled the country, giving the owner the great opportunity to explore the US. It's now tucked away, parked and here at Menlo Pond waiting for you to experience and enjoy the comfort of all it has to offer: *Queen size bed *Large couch *Full bath *Full stove/oven *Air conditioning *Large sink *concrete countertop *Butcher Block *outside picnic table, Barbque and small fire pit

15% off, Private pond, BBQ, 4-min to village, AC

"Pictures understate this well-appointed home. The beds were so comfortable and the pond is so tranquil!" -Kate, May '24 Newly renovated, perfect for groups of friends, couples, and families. Large (1,700+ sq. feet), quiet, 3-bedroom home 4 min to the Village and a 7-min Uber to Rhinecliff train station (2h to Penn Station). Close to hiking, skiing, grocery stores, shops and restaurants. Back yard features a tear-drop pond, BBQ, firepit, and large dining area.

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Our Little Creek Cabin is a place to pause. The cabin is located next to a rushing creek, where you can soak in a wood fired hot tub while listening to the sounds of the water. We are minutes from Candlewood Lake & Squantz Pond, where you take take our kayaks out. There are many wineries, breweries, towns to explore, antique shops, ski mountains, and beautiful hiking trails. Here you can simply open the windows to listen to natures sound machine!

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.