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.

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Guest favorite

Home in Athens

4.94 out of 5 average rating, 114 reviews

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, and work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking trails, art galleries, antique shops, and cultural centers.

Guest favorite

Home in Hudson

4.95 out of 5 average rating, 132 reviews

Hudson Retreat w/ Hot Tub, Fireplace + Fire Pit

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Guest favorite

Home in Ghent

4.97 out of 5 average rating, 36 reviews

Heated Pool + Barrel Sauna at Country Estate

Bring the whole family (6BR, 3.5Bath-sleeps 14) to this amazing 4500 sq ft country escape in Ghent, backing up to a farm with horses & peacocks. Spanning ~5 acres with no neighbors in site, and Berkshire views, it's tough to not feel at peace . Relax poolside, in the outdoor sauna, bbq in the screened in porch, and cook in the chef's kitchen. Dining table seats 12. 2x sitting rooms. Late night watch the 65" flat screen in the Entertainment Room or sit by the fire pit. 10 min to Hudson & Chatham.

Guest favorite

Farm stay in Red Hook

4.99 out of 5 average rating, 146 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.

Guest favorite

Townhouse in Hudson

4.95 out of 5 average rating, 201 reviews

Palazzo Hudson: Luxury Pool, Hot Tub, and Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & the Blue Library-Lounge Barn. A home for all seasons, you'll experience inspiration and relaxation in the warm and whimsical spaces of our unique light-filled home's art, books, music, luxury spa features, outdoor patios, deck, and gardens. A quick stroll to restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Guest favorite

Home in Egremont

5 out of 5 average rating, 16 reviews

The Catamount Haus w. Pool/Hot Tub

Welcome to the Berkshires! Located almost across the street from the Catamount Ski Resort - come unwind with some fun, peace and adventure. This 4 bedroom 4 bath sits on a 5 acre property nestled amongst the trees with a private pool, hot tub and Mountain View ’s to gaze at. Dine at the quaint, hip restaurant in little cat lodge next to the ski resort, have coffee in Hillsdale at Cook& Larder. Or check out the shops in Great Barrington. There is a ton to do in the Berkshires all year long!

Guest favorite

Home in Catskill

4.97 out of 5 average rating, 37 reviews

Hudson Valley & Catskill Mountain Views • Hot Tub

Welcome to our upstate NY escape, where breathtaking mountain views greet you. Lounge by the heated pool (summer), unwind in the hot tub, or share stories by the fireplace—each moment is an experience. Love to cook? Our chef's kitchen awaits. Step outside to immerse yourself in nature’s serenity. Explore nearby trails, lakes, wineries, and charming towns. Minutes to Hudson (15 min), Windham (30 min), and Hunter (45 min). An oasis of tranquility awaits—book now for your unforgettable retreat!

Guest favorite

Guest suite in Hudson

4.99 out of 5 average rating, 83 reviews

Le Soleil Suite - Fire Pit and Views Near Hudson

A charming one-bedroom suite with a private backyard in a rural neighborhood 10 minutes by car from downtown Hudson. Your rental is a private unit next to the main house with full kitchen, bathroom, electric fireplace and private backyard grill, firepit and pool (June to Sept.). Watch sunset over the Catskills from the living room. 1 Br with queen bed, 1 pullout sofa, 1 twin mattress upon request. Close to Hudson, hiking, skiing, farm stands, Olana and Art Omi. IG: @lesoleilsuite

Guest favorite

Home in East Chatham

5 out of 5 average rating, 7 reviews

Stylish Rural Sanctuary

Recently re-opened for short term stays! Just minutes from Chatham, NY, and nestled in the heart of the Hudson Valley, this serene home on over 8 acres offers breathtaking mountain views. Impeccably renovated in 2022, it seamlessly blends the charm of 18th-century Shaker architecture with the sleek elegance of modern Scandinavian design. Indulge in lightning-fast fiber internet, large smart TV, top-tier appliances, including a Miele fridge, Bertazzoni stove, Bosch dishwasher, and more!

Guest favorite

Home in Hudson

4.93 out of 5 average rating, 242 reviews

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

Guest favorite

Home in Athens

4.94 out of 5 average rating, 35 reviews

Modern & Cozy Lake Oasis ~ Hot Tub ~ Games ~ View

Step into the spacious and entertaining lakefront 3BR 3Bath getaway nestled on the shores of the picturesque Sleepy Hollow Lake near the charming town of Athens, NY. Grab the kayak and explore the lake, or lounge the day away in the luxurious hot tub with breathtaking views in the background. ✔ Game Room ✔ Outdoors (Private Hot Tub, BBQ, Fire Pit) ✔ Lake Access (Kayaks, Paddleboard, Canoe) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Community Amenities (Seasonal Pools, Sports) See more below!

Guest favorite

Cabin in Craryville

5 out of 5 average rating, 78 reviews

The Copake Cabin - A rustic-modern retreat.

Heated pool open for the season! A quiet place to get away from it all. Modern log cabin with 3 bedrooms and lots of amenities. A private heated pool, outdoor spaces, wood-burning fireplace and outdoor fire pit. For those working remotely, there is super-fast WiFi and a designated work space. Close to the best of the Hudson Valley and the Berkshires. There is a large lake nearby for boating, swimming, and kayaking in the warmer months. Skiing and sledding in the winter.