Holiday rentals with a pool in Putnam County

Getaway to 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!

Cold Spring Mountain Retreat

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!

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.

City Escape | Heated Pool | Hot Tub| Fire Pit

Welcome to your peaceful Mahopac retreat designed for families and friends seeking a quiet escape. Our home is a sanctuary for leisure. We do not allow parties, large groups, or disruptive behavior, and we appreciate guests who respect our neighbors. The home features 3 spacious bedrooms, 3 modern bathrooms, and soaring vaulted ceilings that create a bright, airy feel. With serene pond views, cozy spaces, and family-friendly amenities, it's ideal for swimming, lounging, and making memories.

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.

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 Mountain Lakes Park. Horse shows at Old Salem Farm, apple picking, farmers markets, great restaurants and NYC bound train nearby. 3 bedrooms + finished basement sleeps 7 and has all the comforts of home, including a kitchen stocked with culinary tools and staple ingredients. Great wifi and 2 desks makes it easy to work remotely!

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.

Gorgeous Garrison Gem: Pool, Sauna, Hot Tub & More

Escape the hustle and bustle of city life and unwind in the peaceful surroundings of this luxurious retreat. With a sauna, steam room, and pool, our home offers something for everyone. Whether you are enjoying the spa like amenities or cozying up by the wood-burning stove you will have an incredible time staying with us. Don't wait, book your perfect getaway now and recharge your mind, body, and soul at our idyllic oasis!