Accommodation 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Ghent

4.87 out of 5 average rating, 270 reviews

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.

8 – 15 Dec

$2,520 AUD total

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.

2 – 9 Dec

$6,758 AUD total

Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private downstairs apartment with your own entrance. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. Upstairs is my family- a 6 year old boy and medium-sized dog- you will hear us! Sometimes we have friends and family visiting. In the summer you may see us at the pool with them. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :-)

10 – 17 Sept

$1,869 AUD total

Guest favourite

Guest suite in Hudson

4.98 out of 5 average rating, 57 reviews

Le Soleil Suite - near Hudson with pool

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

29 Sept – 6 Oct

$1,777 AUD total

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 227 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

13 – 20 Sept

$6,470 AUD total

Guest favourite

Townhouse in Hudson

4.94 out of 5 average rating, 194 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, 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.

27 Oct – 3 Nov

$10,605 AUD total

Guest favourite

Home in Stuyvesant

4.96 out of 5 average rating, 46 reviews

Red House on the Hudson

This Spacious, modern , 2 bd, 2 bath has everything you could need to relax and enjoy all the Hudson Valley has to offer. From the house or pool deck you’ll catch sunsets over the Hudson River. The house is fully stocked with fire pit, grill, WiFi, Netflix, Central Air, with full kitchen and supplies. Within walking distance there is riverfront access and a charming Mexican restaurant. Hudson NY is an easy 15 minute drive and offers easy dining, antiquing, shopping and more.

31 May – 7 June

$3,544 AUD total

Guest favourite

Bungalow in Great Barrington

4.91 out of 5 average rating, 109 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!

7 – 14 June

$6,570 AUD total

Guest favourite

Holiday home in Hudson

4.95 out of 5 average rating, 112 reviews

Private Hudson Retreat w/ Hot Tub + Fireplace

Escape to Falls Road – a private mid-century home nestled at 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 deck, propane grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

30 May – 6 June

$4,072 AUD total

Guest favourite

Cabin in Craryville

5.0 out of 5 average rating, 58 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.

13 – 20 Jan

$7,204 AUD total

Guest favourite

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

New Tiny House living space on 30 private acres with a mile of walkable trails in Beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a Queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in ground pool and renovated barn pool house. Enjoy the 6 person Sauna year round. ** Pool closed Mid-October - Mid-May, Confirm before booking.

8 – 15 July

$2,595 AUD total

Guest favourite

Home in Catskill

4.93 out of 5 average rating, 164 reviews

The Grandview | Catskill, NY

Guest will be greeted with crisp, clean linens, extra comfy bedding, and a spacious atmosphere pleasantly appointed to ensure a cozy stay. The Grandview is a 5 Bedroom 2 Bathroom property that has been appointed specifically for Airbnb guests. This 1890’s Victorian has been offers both old world charm and modern amenities throughout. We're happy to have you enjoy the space as much as we do.

7 – 14 Aug

$8,541 AUD total