
Vacation rentals with a pool in Poughkeepsie
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Poughkeepsie
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Entire Home (private pool), Event Friendly
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.

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

Scenic River View Escape | New Paltz
Unwind in nature. House is located on the river bank with river views and surrounded by tall trees with a huge porch and private backyard. The house was recently renovated with all the modern amenities. The place breathes with tranquility and peace and was stylishly decorated with a lot of care and consideration to guests' experience by an experienced host. Just come as you are and enjoy as we have all you need here including top notch complimentary tea, coffee, yoga mats and much more

New Paltz dog friendly retreat w/salt water POOL
New Paltz dog friendly retreat is a wonderful place to explore the Hudson Valley. 7min drive to downtown New Paltz. 10min to Minnewaska state park & Mohonk preserve. Our very large fenced yard & heated 27ft salt water pool is for your private use during your stay. A signed pool waiver will be required. Heating pool fee is $20 daily. Dog fee $100 per dog. Carolyn whom lives on site in a completely separate studio is there to trouble shoot any issues & keep the pool sparkling clean.

Peace & Privacy - High Falls (hot tub & salt pool)
Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.

The Little Shelter at Gunks EcoLodge
Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Tyrolean Style Country House in Saugerties, NY
Tyrolean style, two family house on two acres, (owner and family are onsite and lives in the bottom unit) fully furnished 3 bed, 2 bath home, fireplace. AC in master and living room only. WIFI throughout. Guests have separate parking, entrance, back deck with a big table & 8 chairs. The house is newly renovated, new luxurious bedding in each bedroom. Wake up surrounded by trees and to a beautiful sunrise. Perfect for a romantic weekend or family vacation.

The Harvest Guest House~ Hidden Gem with Pool
Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.
Fenced & Salt Water Pool | Cozy Catskills Cottage
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.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.
Popular amenities for Poughkeepsie rentals with a pool
House rentals with a pool

The Hudson Valley Hideaway

The Bluff: Designer | Views | Pool | Hot Tub

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hudson River Sunset Getaway

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

MODERN FARMHOUSE in the WOODS

Upstate Modern Scandinavian Barn in the Catskills

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Condo rentals with a pool

Cozy Gem with Mountain Views

Lovely 1 Bedroom/Pool/Hot Tub/King Bed/Ski In/Out

Windham Condo

Hideaway Windham/Hunter Fireplace, Snow & Skiing

One bedroom condo at Mountain Creek Resort

Appalachian Lodge Top Floor w/views

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna
Other vacation rentals with a pool

Catskills Creek | Forest Views, Hot Tub & Pool

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Luxe Wooded Modern Getaway Retreat + Spa

River-to-Ridge Trail Retreat with Pool and View

Arkadia House Mid-century retreat with pool & view

Eco Cottage in the Woods

Country retreat on 4 private acres

Hudson Valley Highland Retreat w/ Pool
Quick stats about vacation rentals with a pool in Poughkeepsie

Nightly prices starting at
Poughkeepsie vacation rentals start at G$29,294 GYD per night before taxes and fees

Verified guest reviews
Over 10 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Poughkeepsie rentals

5 Average rating
Poughkeepsie stays are highly rated by guests—averaging 5 out of 5!
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- Rentals with pools Dutchess County
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- Rentals with pools United States
- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Windham Mountain
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Mount Peter Ski Area
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Bear Mountain State Park
- Wawayanda State Park
- Opus 40
- Benmarl Winery
- Storm King Art Center
- Mountain Creek Water Park




