Vacation 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

Home in Stormville

4.94 out of 5 average rating, 156 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

Oct. 17 – 24

$1,175 CAD per night

Guest favourite

Cottage in Clinton Corners

4.89 out of 5 average rating, 155 reviews

Tranquil Cottage in the Country

Beautiful three bedroom cottage located on a pretty knoll with private access. Heated pool and outdoor living, in a peaceful country setting - with all the tranquil beauty and amenities of the Hudson Valley. Only 1.5 hours from Manhattan and 15 minutes drive to the historic town of Rhinebeck. Great for a weekend getaway. House is perfect for all four seasons; cool in summer and warm in winter. Beautiful decor and suitable for professional people needing an escape from the stress of the city!

Sep. 27 – Oct. 4

$901 CAD per night

Guest favourite

Apartment in Kent

4.93 out of 5 average rating, 127 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

Oct. 29 – Nov. 5

$239 CAD per night

Guest favourite

Farm stay in Red Hook

4.99 out of 5 average rating, 126 reviews

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Just 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, Washer/Dryer, Fridge/Freezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Gas Fireplace & Cable TV 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.

Jul. 9 – 16

$920 CAD per night

Guest favourite

Apartment in Wappingers Falls

5.0 out of 5 average rating, 174 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.

Oct. 8 – 15

$307 CAD per night

Guest favourite

Farm stay in Rhinebeck

4.94 out of 5 average rating, 172 reviews

Majestic Oasis in Rhinebeck w/ Hot Tub & Pool

1100' sq chef's kitchen, 6 bedrooms, 3.5 bathrooms, 60' heated pool (summer), all-year-round hot tub, fireplace, twenty acres, swimming pond with dock, grounds are tick protected, rowboat, ice skating, sledding, giant trampoline, picnic table, rolling meadows, goats, bunnies to pet, + chickens to provide fresh eggs. Automatic generator. Ex-Broadway summer stock theater on the grounds (with well-maintained concert piano, for use by serious musicians only), may be rented additionally.

Feb. 8 – 15

$1,450 CAD per night

Guest favourite

Apartment in Salt Point

4.91 out of 5 average rating, 115 reviews

Beautiful & Secluded Hudson Valley Rustic Getaway

Welcome to Ridgeback Farm at Salt Point! Newly renovated Hudson Valley rustic 1 bedroom apartment on former horse farm. The apartment is located above the barn, next door to the caretaker's apartment. Enjoy 22 acres of beautiful grounds, paddocks, heated pool, hot tub, and 3 ponds. Explore the property and all the Hudson Valley has to offer. Close to restaurants, cafes, Quattro's farm store, antique shops, Village of Millbrook, Innisfree Gardens, skiing. Hosts reside on the property.

May 29 – Jun. 5

$661 CAD per night

Guest favourite

Guesthouse in Stanfordville

4.92 out of 5 average rating, 164 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.

Sep. 1 – 8

$176 CAD per night

Guest favourite

Home in Staatsburg

4.98 out of 5 average rating, 105 reviews

Hilltop Escape ~ 25 acre private retreat

Relax and take in the views! Pets are free! 90 minutes from Manhattan and 5 miles from the Taconic Parkway rests the renovated "Hilltop Escape." Indoor/outdoor living, clean mid-century design, 180-degree 50-mile view into the Catskills, 25 acres of privacy with woodland walking trails and a heated saltwater pool. Omega Institute, Vassar, Marist, Culinary Institute of America, Bard and great restaurants in the village of Rhinebeck all less than 20 min away!

Apr. 18 – 25

$1,091 CAD per night

Guest favourite

Cottage in Rhinebeck

4.87 out of 5 average rating, 147 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 used 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!

Apr. 21 – 28

$243 CAD per night

Guest favourite

Home in Rhinebeck

4.96 out of 5 average rating, 164 reviews

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 total solitude.

Dec. 20 – 27

$849 CAD per night

Superhost

Home in Lagrangeville

4.84 out of 5 average rating, 120 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Whether you seek a nook to escape to or room to gather all together, this expansive and historic farmhouse offers the chance to do so in comfort. Highlights include multiple working fireplaces and a piano, with plenty of space to lounge by either, as well as an expansive library. The formal dining room has a 10 foot table, and the kitchen is well-equipped to support it. The pool is open Memorial Day - Labor Day.

Sep. 22 – 29

$920 CAD per night