Holiday rentals with a pool in Putnam County

Gilbo's Landing - Escape to Cold Spring

A perfect getaway for families and friends! Spend the summer by the pool and the winter by the fire. The house is located 0.5 mile from Cold Spring's Main Street and a mile or so from the Metro North train station, close to Beacon and West Point. With indoor and outdoor fireplaces, a wood burning stove, well stocked kitchen and pool, this 4 bedroom home truly is the perfect gateway to the Hudson Valley! There is so much to do in the area- art museums, epic hikes and vistas, and historical sites.

The Lodge-Your own hillside estate-45 miles to NYC

Enjoy the elegance of your own Lodge set on 20 acres. You'll feel like you're at your a private resort w/ a pool, manicured grounds, hot tub, multiple patios to gather & dine at, private trail, gardens, massage chair & table, 2 offices & fireplace. Relax in an Adirondack inspired Great Room w/ a massive fireplace, 3 bedrooms & 3 baths + 3 single day beds. Hiking, biking, kayaking & Hudson Valley activities abound. 25 mins away from Cold Spring. 5 mins from Taconic Pkwy & 20 mins from the train.

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)

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.

NYC Escape- Designer Pool, Hot Tub & 6-Acre Forest

Experience the ✨ENCHANTED ESCAPE✨ – stunning luxury forest retreat just 75 mins from NYC 🌲! Enjoy the home's luxury design, lounge poolside with a chilled rosé, hike our private 6 acres of lush Hudson Valley, soak in our spa quality hot tub, or stargaze at night, this is where your ultimate "Out of Office" spring & summer sanctuary! Perfect home for a getaway to explore the Hudson Valley, winery tours and more! Now offering CONCIERGE services to make your stay unforgettable! 💫

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!

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 Luxe Retreat w/ 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!

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

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.

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

Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.