
Holiday rentals with a pool in Hudson Valley
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hudson Valley
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

midcentury mod * HOT TUB * walk out trail 2 mohonk
A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. fireplace, 5 person hot tub short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village THE WHOLE PLACE IS YOURS- HOUSE, PROPERTY, POOL (open 5/1-9/30) and HOT TUB (open 9/30-5/1)

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!

4Br Mountain Brook House on 130 acres w/ trails
Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open May - October 26, 2025. 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.

Palazzo Hudson: Luxury Home w/Pool, Hot tub, Sauna
Welcome to Palazzo Hudson! The only private vacation home in Hudson proper with a deluxe sauna, cedar hot tub, seasonal in-ground pool, chef's kitchen, & a pool-side lounge with a fireplace & art library! 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 & the Upper Depot District.

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.

Upstate Modern Scandinavian Barn in the Catskills
Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Mtn View Lux Dome w/ Heated Plunge Pool
This luxury dome is a modern home perched on a mountain top. Our aim is to combine the comforts of a large hotel suite with all the healing qualities of nature. Venture out or hike our own trails leading to a pond and a stream in the woods. Suited for long term WFH stays! We have Fiberoptic internet (ethernet avail) and plenty of space for your setup. Stroll the property at lunch or jump in the heated plunge pool between calls. Ask me about a special offer for long term stays. (14 days +)

Experience The Zen House
Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!

Woodstock Historic Artist Estate- The Museum House
The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

The Copake Cabin - A rustic-modern retreat.
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.

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome
BoHo Farm House is a luxe, stylish 3BR/3BA retreat on 8 scenic acres in Accord, Hudson Valley—with a fully fenced area for dogs to roam safely. Featured in PureWow, this Scandi-style escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. Dog-friendly luxury meets fall and winter serenity!
Popular amenities for Hudson Valley rentals with a pool
House rentals with a pool

Hudson Valley & Catskill Mountain Views • Hot Tub

Canopy Hill House - Luxury w/ Mt View+Hot Tub+Pool

Modern Barn on 12 acres w Sauna, FirePit+swimming

Happy Hemlock | Modern Luxury Retreat

Birch & Buck - Stunning Views near Hudson & Hunter

Sauna | Movie Theater | Hot Tub | Dogs OK |Firepit

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Condo rentals with a pool

Hideaway Windham/Hunter Fireplace, Snow & Skiing

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Winter Dream! The Handle Lodge at Snowtree Condos

Comfy Studio at Mountain Creek Resort

Appalachian Lodge Top Floor w/views

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

Updated 1BR Retreat at Mountain Creek Pool #342

All New Chic Ski in/out King bed
Home rentals with a private pool
Magnificent Hudson River Estate with Infinity Pool and Spa

Rhinebeck Country Living with a Modern Twist
Fully Fenced 10 Acres | Cozy Cottage w/ Kid Gear
Catskills Winter Ski Retreat – Near Belleayre!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Hudson Highlands State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Mount Peter Ski Area
- Norman Rockwell Museum
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Plattekill Mountain
- Taconic State Park
- Mohawk Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Beartown State Forest
- Opus 40
- Berkshire Botanical Garden
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