Holiday 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, 111 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!

4.98 out of 5 average rating, 55 reviews

Home in Catskill

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!

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, 105 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.

Bungalow in Great Barrington

4.92 out of 5 average rating, 118 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!

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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Columbia County rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.75 out of 5 average rating, 60 reviews

Modern Glass House

AlisonRating, 5 stars8 months ago

This was our second time staying in this special house. Waking up in the cozy bed and feeling like you are sleeping in the beautiful woods with deer just outside the giant expansive windows is really something. The property and surroundings are gorgeous, private and serene. The house itself is perfect for our family. The bedding and linens are quality. The space is charming and magical.

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 stars3 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!

4.92 out of 5 average rating, 59 reviews

16 Acre Hudson Hideaway and Pool

JamieRating, 5 stars4 months ago

We loved our upstate getaway to the Hudson area. The house is soooo cute, beds are comfortable, and stunning views of nature/wildlife (we saw deer every day). We were so pleased with how well equipped the kitchen was for cooking. It was a short 10-15 minute drive to bustling Warren Street. The hosts were incredibly helpful & responsive throughout the weekend. It snowed pretty hard and a team was there first thing in the morning to plow the driveway and throw down salt. Thanks for a wonderful stay!! ♥️

4.98 out of 5 average rating, 60 reviews

Home in New Lebanon

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars3 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!

4.96 out of 5 average rating, 53 reviews

Home in Athens

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

DanielleRating, 5 stars2 weeks ago

We loved Kathryn’s place! It was so peaceful and pretty, we loved having lake access, and it was convenient to drive to several local towns with great restaurants. The whole family enjoyed the kayaks and the community pool and the lovely outdoor space. My favorite part of the stay was the friendly fox who would visit the property in the mornings. Kathryn was also a wonderful host and responsive to our questions/messages. I would definitely stay here again!

4.99 out of 5 average rating, 74 reviews

Home in Catskill

Catskill Ski Hike Lake Pet Main St Pool

VikRating, 5 stars1 month ago

This place was a rare find for a group of six of us. Upon walking and we were immediately amazed at how nice the place seems. The amenities were great, the space luxurious, and the location was phenomenal. The driving distance to grocery stores and restaurants was easy and there were quite a few stores and restaurants that were walkable as well. In terms of things to do in the area, the location was great. It was very drivable to several walking trails and all the drives were very pretty. Overall, my friends and I would absolutely love to stay here again next time we come back to the area.