Vacation rentals with a pool in Poughkeepsie

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

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

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

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Woodstock Retreat- Heated Pool/Hot Tub/FirePit

Welcome to The Evergreen, our Catskills retreat located just 5 minutes from Woodstock village. Sitting on 3 acres amongst the trees, this property boasts beautiful outdoor space with a heated pool*, hot tub, outdoor dining area, grill, and a fire pit, creating the perfect setting for relaxation and entertainment. This charming property offers 5 bedrooms & 3 full bathrooms- perfect for families or groups of friends. It also features a study, ideal for those who need to balance work and play.

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.

Peaceful and Private Boutique Apartment *Pool*

Welcome to your serene retreat one mile from charming downtown New Paltz! Our pretty boutique apartment offers a peaceful escape, perfect for couples or families. Enjoy the comfort of a private entrance, luxurious king and queen beds, kitchen, stocked coffee bar, and huge yard. End your day with a refreshing dip in our pool or unwind in the hammock. Just minutes from town and hiking trails, and many local activities. Experience the best of New Paltz – book your stay today!

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

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. Please note that 35-40% of the price is fees and taxes from this site.