Holiday rentals with a pool in Dutchess County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Dutchess County

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

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Guest favourite

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

4.94 out of 5 average rating, 196 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Superhost

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

4.88 out of 5 average rating, 165 reviews

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

Superhost

A spacious backyard is highlighted by a shimmering in-ground pool surrounded by lounge chairs and cabana umbrellas. Lush greenery frames the area, creating a tranquil atmosphere. A slide is visible in the pool, and a vibrant blue sky with clouds adds to the inviting scene.

Home in Beacon

4.91 out of 5 average rating, 149 reviews

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

Top Guest favourite

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

4.99 out of 5 average rating, 163 reviews

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.

Top Guest favourite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

4.96 out of 5 average rating, 371 reviews

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.

Top Guest favourite

Apartment in Wappingers Falls

5 out of 5 average rating, 227 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

Top Guest favourite

A comfortable living room is highlighted by warm-toned walls and polished wood floors. A sectional sofa offers spacious seating, complemented by a rustic coffee table. A brick fireplace adds character, while natural light filters through white curtains on multiple windows.

Home in Saugerties

4.94 out of 5 average rating, 123 reviews

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.

Superhost

The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.

Home in Kingston

4.81 out of 5 average rating, 111 reviews

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.

Top Guest favourite

A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.

Guesthouse in Stanfordville

4.93 out of 5 average rating, 186 reviews

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.

Guest favourite

A charming blue house is nestled among lush green trees. A hammock is strung between two trees, while Adirondack chairs are arranged on a stone patio nearby. A small table and a grill are positioned in front of the house, complementing the serene outdoor setting.

Cottage in Rhinebeck

4.87 out of 5 average rating, 210 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Top Guest favourite

The house features a wraparound deck adorned with potted plants, while tall evergreen trees provide natural framing. A bright blue sky complements the white exterior of the home, creating a welcoming outdoor space. Lush greenery surrounds the property, enhancing its tranquil atmosphere.

Home in Saugerties

4.92 out of 5 average rating, 116 reviews

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.

Top Guest favourite

Guest suite in Hyde Park

4.98 out of 5 average rating, 239 reviews

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.