Vacation rentals with a pool in Putnam County

Summer Adventures in Cold Spring at Gilbo's

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!

Charming contemporary cottage with lap pool

Formerly an old schoolhouse, this cottage brings a unique charm and style to the area that even Barbara Streisand enjoyed a stay while filming the acclaimed film, "Hello, Dolly!". With 3 bedrooms, all with Casper mattresses and luxurious linens, up to 5 beds, and 2 full baths, a fully enclosed lush garden w/lap pool, the cottage makes for an easy accessible escape from the city being just one hour north by car or train. Conveniently located between Garrison station and Cold Spring village.

Enchanted Escape | POOL, LAKE, Concierge Services

Experience the ✨ENCHANTED ESCAPE✨ – a stunning retreat just 75 mins from NYC! Dive into the POOL, soak in the HOT TUB, relax in the STEAM SHOWER or JACUZZI, and take in breathtaking views 🌲🌅. With LAKE ACCESS, hiking trails, skiing, water parks, wineries, and charming towns nearby, adventure awaits. 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! 💫

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.

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!

Cold Spring Gem

Quiet, modern, and comfortable retreat surrounded by nature. The perfect combination of relaxation and outdoor activities, secluded and quiet. Located on seven rustic acres with creek running through the back of the property. 2 bed, 3 bath, movie/playroom, gourmet custom kitchen, screened in porch and beautiful outdoor sundeck. Huge 40ft in ground (heated) swimming pool, fire pit, 2xBBQ grills. 10 min from the beautiful town of Cold Spring, 60 miles from Manhattan.

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.

City Escape | Heated Pool | Hot Tub| Fire Pit

Welcome to our charming house located in the picturesque town of Mahopac, NY. This stunning property is perfect for families or small groups of friends looking for a peaceful and relaxing getaway. Our house boasts three spacious bedrooms with comfortable beds, three modern bathrooms, and gorgeous vaulted ceilings throughout. You'll love the bright and airy feel of the house as well as the tasteful decor and comfortable furnishings.