Vacation rentals with a pool in Columbia County

4.96 out of 5 average rating, 156 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!

4.99 out of 5 average rating, 96 reviews

Guest suite in Hudson

Le Soleil Suite - Pool, Views 10 min From Hudson

A charming one-bedroom suite in a rural neighborhood 10 minutes by car from downtown Hudson. Your rental is a private, independent unit next to the main house. It has a full kitchen, bathroom, electric fireplace and a private backyard with a grill, firepit and pool (June to Sept.). If we are around, we give you privacy. Watch sunset over the Catskills from the living room. 1 Br with queen bed, 1 pullout sofa, 1 fold-out twin upon request. Close to Hudson, hiking, skiing, Olana and Art Omi.

4.81 out of 5 average rating, 106 reviews

Cottage in Hudson

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

1 minute off Warren St - salt water pool and hot sauna respite! No expense spared reviving this Historic 18th century 80 acre estate - heated pool, cedar barrel sauna, heated bathroom floors, original wood finishes, french door patio under stain glass windows from NYC’s iconic Chelsea Hotel. You’ve found the perfect combination of transcendentalist oasis with modernity providing a most comfortable stay. Enjoy a dip, steam, rolling meadows, goat petting, cocktail by fire on your patio!

4.95 out of 5 average rating, 128 reviews

Home in Germantown

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.

4.91 out of 5 average rating, 112 reviews

Home in Catskill

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!

5 out of 5 average rating, 16 reviews

Home in East Chatham

Stylish Rural Sanctuary with POOL!

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!

4.93 out of 5 average rating, 244 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

4.96 out of 5 average rating, 353 reviews

Cabin in Red Hook

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.

4.9 out of 5 average rating, 106 reviews

Chalet in Athens

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.

4.99 out of 5 average rating, 74 reviews

Home in Tivoli

Hudson Valley Getaway near Bard, Hudson, Rhinebeck

Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. POOL WILL BE CLOSED AFTER 9/24/2024 FOR THE SEASON. NOTE: For bookings during pool season, guests will be asked to sign an agreement with rules relating to the pool. Please contact us for more information.

4.88 out of 5 average rating, 318 reviews

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 Hudson. 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.

4.97 out of 5 average rating, 156 reviews

Tiny home in Ghent

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Columbia County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 29 reviews

Home in Old Chatham

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

IdaRating, 5 stars4 weeks ago

We had a good stay at Victoria’s farmhouse. The location is really peaceful and relaxing, surrounded by nature—perfect if you’re looking to unplug a bit. The house itself is beautiful and very comfortable, with unique interiors that feel like something out of a design magazine. Victoria was easy to communicate with and helpful when we had questions. It’s a bit off the beaten path, which we liked, but still just a 15-minute drive to shops and about 30 minutes to the train and some great restaurants in Hudson. Overall, a lovely spot for a quiet getaway.

4.75 out of 5 average rating, 61 reviews

Modern Glass House

CelesteRating, 5 stars1 day ago

Stunning property! Had a great stay

5 out of 5 average rating, 41 reviews

Home in Pine Plains

Stunningly Designed Luxury Home w/ Pool & Hot Tub

NaomiRating, 5 stars4 weeks ago

We had an amazing relaxing weekend. The beds are comfy, pool heated, quiet serene area. All around perfect weekend getaway. The house was clean and had everything we could have possibly needed.

4.93 out of 5 average rating, 43 reviews

Home in Athens

Catskills Lake Community Escape near Hudson

TinaRating, 5 stars4 weeks ago

House is very comfortable and clean in a convenient location to Hudson and other local attractions. The host is very responsive, helpful and accommodating. There is the additional bonus of having access to the lake and the amenities in Sleepy Hollow community, but we were so busy with hiking, visiting a winery and dining at some great restaurants we didn’t use it! We had a really great long holiday weekend and would definitely recommend staying at this air bnb!

5 out of 5 average rating, 31 reviews

Home in Egremont

The Catamount Ski Haus w. Pool/Hot Tub

JulieRating, 5 stars4 weeks ago

This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!

4.98 out of 5 average rating, 60 reviews

Home in New Lebanon

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars4 months ago

The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

4.94 out of 5 average rating, 77 reviews

Hudson River Sunset Getaway

AmandaRating, 5 stars2 months ago

The view from this house is amazing and my family loved putting up the blinds every morning to gaze out. The sitting room and bedrooms were so lovely, homey, and comfortable to lounge in. Maura was welcoming and proactive in communication and had beautiful flowers waiting in the living room for us.