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

4.95 out of 5 average rating, 133 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, kayaks, 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, or work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking, art galleries, antique shops, and cultural centers.

Guest favorite

Home in Hudson

4.95 out of 5 average rating, 152 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

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!

Superhost

Tiny home in Ghent

4.95 out of 5 average rating, 131 reviews

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny Small House - 600 Sq ft. of new living space on 30 private acres with walkable trains in Beautiful Columbia County. Secluded privacy surrounded by nature. House has everything you need and sleeps 4 with two twin loft beds. Enjoy the pool and renovated barn pool house. In the Winter stay warm by the wood stove. Enjoy the 6 person sauna year round. Restaurants close by or stay in and enjoy the property. Located 9 miles from Hudson and 3 miles from Chatham and Kinderhook. Near OMI Arts Center.

Guest favorite

Home in Germantown

4.94 out of 5 average rating, 126 reviews

Hilltop modern with stunning mountain views

Beautiful modern residence with a pool & fireplace in Germantown. Fantastic as a weekend getaway or longer-term rental. In the front, stunning mountain views wrap around the master bedroom, kitchen, living room and deck. Out back, a spacious yard and rolling hills. Grill & eat on the big pool deck, lounge in chaises. Fully equipped kitchen, washer & dryer, and *fast wifi*. Perfect for remote work, and each space has its own desk. Shop, walk, hike, ski: Close to Hudson, Olana & Catskills.

Superhost

Home in Egremont

5 out of 5 average rating, 4 reviews

Fabulous Heated Pool, Screen Porch, Ping Pong!

Stone Hill is an immaculate property with big views! Amenities include: 3+ bedrooms, 3 full baths, sleeps 9 max. High speed internet/wifi, central AC, lovely gas fireplace, all stainless Bosch appliances and a gas range, heated pool with several areas of outdoor furniture, propane BBQ grill, sun deck, 3-season sunny screened porch/sunroom, 2-car garage, gym, ping-pong table, washer/dryer, portable crib, high chair and more! Pet friendly for non-shedding hypoallergenic pets only with pet fee.

Guest favorite

Home in Catskill

4.9 out of 5 average rating, 104 reviews

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

Welcome to our Stunning 4-Bedroom, 4-Bathroom Modern Farmhouse with Private Pool, Hot Tub, and Amazing Views! - Newly Re-Built (2023) - Tastefully Decorated, Modern Finishings - Amazing Mountainside Panoramic Views, Lots of Sunlight - Over 2,000 Square Feet of Outdoor Patio Space (BBQ, Fire Pit, Games) - 5min to I-87 & Catskill Downtown, 15min to Hudson (Amtrak), 25min to Windham (Ski/Golf), 35min to Hunter Ski Area Perfect for Vacationing, Entertaining, Group Retreats and Family Gatherings!

Guest favorite

Home in Hudson

4.93 out of 5 average rating, 243 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

Top guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. 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 favorite

Townhouse in Hudson

4.95 out of 5 average rating, 211 reviews

Palazzo Hudson: Luxury Home with Pool, Spa, 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 & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Guest favorite

Chalet in Athens

4.89 out of 5 average rating, 103 reviews

Waterfront Lake Home, close to Hunter & Windham

Located w/in the Sleepy Hollow Lake community, adjacent to The Hudson River, offering an unrivaled location to experience all that Hudson has to offer. The quaint community of Sleepy Hollow is 30 minutes from Hunter Mountain & Wyndham Mountain, and 20 minutes from Hudson. The community enjoys its own beach, boat ramp, tennis courts, bocce ball court, 2 swimming pools (seasonal), outdoor full-size basketball court, a baseball/softball field, volleyball court, and a golf driving range.

Guest favorite

Bungalow in Great Barrington

4.91 out of 5 average rating, 117 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

Superhost

Cabin in Valatie

4.9 out of 5 average rating, 41 reviews

Private Cabin in the Woods w/ Hot Tub near Hudson

This spacious cabin-style home is surrounded by towering trees. It's perfect for escaping from your worries and enjoying nature at its finest. Venture out to Hudson, NY, where you can find many great restaurants and bars, or explore Hudson Valley's best hiking trails, and scenic views just minutes away. Whether you're looking to unplug from technology or work on your next great novel or chill with the family, this place has everything you need to get away from it all.