Holiday rentals with a pool in Dutchess County

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway, a stylish family friendly home tucked away in the corner of Beacon, off the shores of the Hudson. 4 Bedrooms, 2 bath, pool+hot tub home, stocked kitchen, dining room, chic living room w/ 85"TV, 1 King, 2 Queens, 1 Twin XL, with fast internet (1gb), dedicated workspace & A/C. Amenities galore, outdoor space w/grill, firepit and fenced pool w/ slide & diving board. Experience a little slice of Beacon in this cozy home with modern city comforts,1.5 miles from DT

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' Rumaan Alam First floor open space includes a fully equipped Kitchen (Viking Range, Dishwasher, WasherDryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Gas Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom

Viewtop Farmhouse-Book now for Autumn fun!

Enjoy View Top Farm House, a rustic, 100+ yr old, farmhouse/former boarding house on 3 beautiful acres, overlooking the Catskill mountains. Enjoy time on the patio by the fire, barbecuing, eating alfresco or swinging in the hammock. Its 15 min to the Rondout, 7 min to the Village of Saugerties. Get breakfast, lunch or dinner out, or cook at home in the large, well stocked kitchen. Minutes from restaurants, antique stores, hiking, and biking. Enjoy many amenities. Well behaved pets are welcome.

Hudson River views with pool and hot tub

The Riverview Terrace House is located in a quiet neighborhood in Kingston NY overlooking the beautiful Hudson River. Just an hour and forty five minutes from NYC it is the perfect get away for family and friends. We welcome you to enjoy the house with 5 bedrooms, 2.5 baths, a pool open during summer months thru Labor Day and a hot tub open year round. Centrally located between uptown Kingston and Rhinebeck you will have access to the all of the great amenities the area has to offer.

Peaceful Hudson Valley Getaway House

Best for families! Relaxing and playful retreat! Come for the hiking, antiquing, HITS shows, farmer's markets, visits to Bard College! Especially KID FRIENDLY with all the necessary amenities. Enjoy the pool, deck, gas grill, fully stocked kitchen, bikes, hammock, fire pit, and open floor plan for gathering and home cooked meals. Feel free to message me if you are looking for specific dates that are marked unavailable. From June - August, 3 night minimum.

On The Hill in Rhinebeck

Perched on a hill, this 1930’s cape with a facelift sits just over a mile from the center of Rhinebeck. The first floor is open between the kitchen, dining area and living room. Two private bedrooms and one full bath are also on the first floor. The master suite is up on the second floor with a huge master bathroom featuring a jacuzzi and glass shower. On the hill you’ll experience tree top views and a wonderful countryside experience.

Lovely country house; stunning view

This 100 year-old home on 83 acres overlooks a beautiful meadow, surrounded by dogwood and maple trees -- breathtaking in spring and fall. The saline pool is open generally between April and October, and surrounded by an abundance of flowers. In the cooler months, an atmospheric wood-burning fireplace makes the cottage cozy. This property is the subject of a book A FIELD OF MY OWN: A Memoir of Place.