Vacation rentals with a pool in Putnam County

Arkadia House Mid-century retreat with pool & view

Located only 75 minutes from NYC, this architectural mid-century retreat is immersed in the scenic beauty of the Hudson Valley. The towns of Cold Spring & Beacon are just a few minutes drive away. As are numerous hikes, such as Breakneck Ridge & Bear Mountain State Park. The area is full of activities from farmers markets, golf, kayaking and galleries (Dia: Beacon, Magizzino). The sparkling pool and garden is perched above the Hudson River with sweeping views. (Pool closed Nov-end of April)

Winter by the Fire in Cold Spring

Gilbo's Landing- the perfect getaway for families and friends! Spend the summer by the pool and the winter by the fire. The house is located about a mile outside of Cold Spring's Main Street/train station (it’s a long walk though so probably best to drive). It’s near Boscobel, close to Beacon (15 min drive) and West Point (25 min drive). With indoor and outdoor fireplaces, wood burning stove, well stocked kitchen and pool, this 4 bedroom home truly is the perfect gateway to the Hudson Valley!

Cold Spring Mountain Retreat: Sun-filled Oasis

Your next mountain retreat is a short drive away from the bustling village of Cold Spring and approximately 90 minutes from NYC! Come let us host you at Cold Spring Mountain Retreat, where your group will be enclosed in the verdant embrace of nature. Experience modern amenities, luxurious accommodations, a beautiful pool with plenty of space to lounge, and unforgettable scenery. Whether you’re looking for adventure or a calm escape, make sure Cold Spring is on your list of places to get away!

The Barger Wixon House

The Barger Wixon House is a family home in the foot hills of the Hudson Valley, built in 1790. A 3 bedroom house with 2 living rooms, a proper dining room, a large eat in kitchen with all the provisions you could need for a big family dinner. Enjoy the attic hang out spot that is a great play area and or movie night! With a big finished patio, heated pool (5/15-9/15) hot tub, and multiple grilling spots you won't need to leave the homestead! Unless you want to go to Cold Spring for coffee.

Beautiful one bedroom apartment pet/pool fees

Light bright and quite in private home, park like property. Please return in same condition, There’s a green pump up water system no food down sink,no feminine or excessive paper products flushed down the toilet. No frying no food or grease down the kitchen sink you will hear the pump. Separate charge through Airbnb pool fee, pool is seasonal, no shoes policy in apartment and please be considerate with the lights, if you’re not using them turn them off no smoking there is a pet fee

North Salem Home with Pool & Great Yard

Relax by pool, curl up by the fireplace or bbq on the covered patio at our pet friendly home in bucolic North Salem. Hike the nature preserve on the street or many others in town. Horse shows at nearby Old Salem Farm, apple picking, farmers markets, great restaurants and close NYC bound train. 3 bedrooms sleeps 6 and has all the comforts of home like a kitchen stocked with culinary tools and staple ingredients. Central A/C, great wifi and 2 desks makes it easy to work remotely!

Billy Joel/JP Morgan Hudson Valley Home 1h to NYC

Come stay in J.P. Morgan's summer home with breathtaking views of the Hudson River! Private saltwater pool & sauna. Billy Joel famously also lived here in the 1970s when he wrote "New York State of Mind" and "Summer, Highland Falls" in the primary bedroom. This is J.P. Morgan's original "Cragston" mansion (he used to take his Yacht up here from Wall Street!). Under 5 minutes to West Point & Bear Mountain 1 hour to NYC Cold Springs & Peekskill are under 20 minutes away

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Hudson Valley Retreat | Hot Tub, Pool & Gym

Enjoy a cozy weekend getaway with friends and family at our spacious Hudson Valley retreat. Just one hour from NYC, nestled between Cold Spring and Beacon, and only 5 minutes from the Appalachian Trail, our home offers the perfect blend of comfort and convenience. With four bedrooms, four bathrooms, a loft gym with Peloton and treadmill, a chef’s kitchen, and a seasonal pool and hot tub overlooking stunning views, this is your ideal escape. We look forward to hosting you!

Winter Retreat, Hot Tub, Close to NYC, Enchanted

Experience the ✨ENCHANTED ESCAPE✨ – stunning winter retreat just 75 mins from NYC! Enjoy the home's COZY VIBES, soak in the HOT TUB, take in breathtaking winter forest views 🌲. Perfect home for hosting your winter family and friend gatherings, ski trips, winery tours and more. Unwind outdoors, stargaze at night, or explore 6 private acres – perfect for families & friends seeking the ultimate getaway! Now offering CONCIERGE services to make your stay unforgettable! 💫

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway — a stylish, family-friendly 4BR/2BA home tucked in the corner of Beacon just 1.5 miles from downtown & the Hudson River. Enjoy a chic living room w/ 85” TV, stocked kitchen, dining room, 1Gb WiFi, workspace & A/C. Sleep soundly in 1 King, 2 Queens & 1 Twin XL. Outside, unwind in the fenced oasis w/ pool, slide, hot tub, grill & fire pit. Modern comfort meets cozy Hudson Valley charm. SPECIAL: 20% OFF all winter stays!

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.