Holiday rentals with a pool in Poughkeepsie

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Quick stats about holiday rentals with a pool in Poughkeepsie

Nightly prices starting at
Poughkeepsie holiday rentals start at ₹13,415 per night before taxes and fees
Verified guest reviews
Over 40 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Poughkeepsie rentals
4.9 Average rating
Poughkeepsie stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with a pool in Poughkeepsie

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

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

ValueFamilyNearby

4.88 out of 5 average rating, 222 reviews

Guest favourite

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

FamilyValueDecor

4.99 out of 5 average rating, 279 reviews

Guest favourite

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

ValueLocationHeating

4.94 out of 5 average rating, 398 reviews

Superhost

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

LocationValueQuiet

4.81 out of 5 average rating, 136 reviews

Top guest favourite

A spacious outdoor area features a modern pool surrounded by wooden decking. Lounge chairs are positioned under large umbrellas, providing shade. The two-story home is visible in the background, showcasing large windows that enhance natural light.

Home in Putnam Valley

Heated Pool, Ultra Modern Home 5B, hot tub, sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

FamilyValueWalkability

4.98 out of 5 average rating, 177 reviews

Top guest favourite

Home in New Paltz

midcentury mod hot tub*walk out trail R2R/Mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 - Sept 21 HOT TUB YEAR ROUND

LocationValuePets

4.98 out of 5 average rating, 549 reviews

Top guest favourite

Home in High Falls

Comfortable & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods, pond and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

FamilyLocationParks

4.98 out of 5 average rating, 124 reviews

Top guest favourite

Flat in Wappingers Falls

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

LocationValueBathroom

5.0 out of 5 average rating, 256 reviews

Guest favourite

Home in New Windsor

Historic Cornwall Farmhouse w/ Sauna & Hot Tub

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

ValueFamilyCleanliness

5.0 out of 5 average rating, 107 reviews

Guest favourite

A serene meadow unfolds beneath a cloudy sky, with lush green grass leading into a gentle expanse of golden fields. Towering trees line the horizon, creating a natural boundary between the open landscape and the dense wooded area beyond.

Farm stay in Ulster Park

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 15% of the price goes directly to this site.

LocationFamilyRiver

4.91 out of 5 average rating, 177 reviews

Top guest favourite

Home in Kerhonkson

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

LocationValuePool

4.97 out of 5 average rating, 120 reviews

Guest favourite

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

A Very Cozy House With a Very Big Yard

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

FamilyValueHospitality

4.94 out of 5 average rating, 414 reviews