Holiday rentals with a pool in Ramapo

Entire Home (private pool), Event Friendly

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Midcentury Modern ZenHouse Sculptor Studio

Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen

Cozy & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods & pond + the canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with patio furniture, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Luxe 10 guest Ski Cabin Pools/Golf/Tennis/Gym/Hike

Gather your crew of 10 and escape to this stunning two-floor cabin, where adventure meets relaxation. Nestled in breathtaking scenery, this stylish retreat offers the perfect balance of comfort and outdoors. Whether you're hiking scenic trails, or simply unwinding, there's something for everyone. Enjoy year-round activities like skiing, snowboarding, mountain biking, wildlife spotting, or exploring the Appalachian Trail. This is more than a getaway it’s an experience you'll never forget!

The Little Shelter at Gunks EcoLodge

Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

The Magic Red Barn with Heated Salt Pool

Experience countryside magic just one hour from NYC! Enjoy nature’s wonderland, nearby farmers’ markets, and scenic trails. Indulge in our heated saltwater pool for a perfect retreat. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn featuring: 1 king, 2 queen, 1 toddler bed, full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests seeking escape. Enjoy complete privacy—no other guests. Fiber optic Wi-Fi.

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 15 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

Hillside villa with 9-mile lake views

Views, views and more views, this luxury getaway embraces the outdoors from every angle. Dine alfresco on the expansive deck, kick back and relax in the outdoor hot tub and spend nights with friends and family shooting pool, sitting by the fire or cooking in the gourmet kitchen. STR Permit#: 21-7747