Vacation rentals with a pool in Columbia County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Columbia County

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

Guest favourite
Home in Ghent
Modern Barn on 12 acres w Sauna, FirePit+swimming
Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.
Jul. 7 – 14
$578 CAD per night
4.87 out of 5 average rating, 259 reviews
Guest favourite
Farm stay in Red Hook
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.
Aug. 25 – Sep. 1
$913 CAD per night
4.99 out of 5 average rating, 125 reviews
Guest favourite
Home in Hudson
Casa Luna Country Retreat with Pool, Hudson, NY
CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143
Jul. 20 – 27
$823 CAD per night
4.93 out of 5 average rating, 227 reviews

Popular amenities for Columbia County rentals with a pool

House rentals with a pool

Guest favourite
Home in Catskill
The Grandview | Catskill, NY
Oct. 9 – 16
$925 CAD per night
4.93 out of 5 average rating, 156 reviews
Superhost
Home in Kinderhook
The Big Yard at Kinderhook
Sep. 9 – 16
$338 CAD per night
4.91 out of 5 average rating, 53 reviews
Guest favourite
Home in Hudson
Secluded classic farmhouse near Hudson-pool+hottub
Jun. 10 – 17
$1,200 CAD per night
4.87 out of 5 average rating, 31 reviews
Guest favourite
Home in Hillsdale
Ives Farmhouse | Retreat in the Hudson Valley
Feb. 5 – 12
$625 CAD per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Craryville
Poets Hill - Modern poolhouse with magical views.
Jun. 8 – 15
$1,039 CAD per night
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Catskill
Hudson Valley & Catskill Mountain Views • Hot Tub
Aug. 1 – 8
$944 CAD per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Great Barrington
Newly Remodeled Private Estate-Pool, Tennis Court!
Nov. 4 – 11
$1,697 CAD per night
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Germantown
Beautiful Riverside Retreat; W/Pool&Mountain Views
Mar. 3 – 10
$969 CAD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Craryville
Hudsonshire - Stylish retreat with a Pool
Jul. 4 – 11
$1,104 CAD per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Coxsackie
Hudson River estate guest cottage
Nov. 23 – 30
$1,176 CAD per night
4.97 out of 5 average rating, 63 reviews
Guest favourite
Home in Athens
Mid century bungalow
Mar. 10 – 17
$376 CAD per night
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Athens
Private Lake House Surrounded by Nature
May 11 – 18
$937 CAD per night
5.0 out of 5 average rating, 14 reviews

Destinations to explore