Family-friendly holiday rentals in Deerpark

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Scandinavian-Style Chalet with Scenic Views

Wake up to hilly views from this Scandinavian-inspired chalet boasting wood-paneled cathedral ceilings, sharp furnishings, and concrete floors. Share a glass of wine with a friend beside a sleek fireplace and live-edge coffee table in a chic living area. Please inform the host if you plan to bring a dog as there is a 15 pound weight limit. Maximum number of guests/visitors/people permitted on the property is 2. The owner lives on the property and is available for anything guests may require.

Delaware Riverfront

This isn’t a cold, clinical, ultra-modern, cooperate-owned product masquerading as a home. Come here for a taste of humanity, surprise, old-fashioned American décor, and an intriguing setting of items not seen over and over again in clone rental units around the area. Rather than trying to transplant an urban style/faux glamour to the Upstate experience, we endeavor to give the comforts and intriguing whatnots, knickknacks, curiosities and lost charms perhaps seen in your grandparents’ home.

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Cozy Cottage w/ Infrared Sauna

Escape to a serene, nature-inspired cottage nestled on the Shawangunk Ridge. Relax by the warm gas fireplace, gather around the handmade dining table crafted from 100-year-old reclaimed wood, or unwind in the private infrared sauna, accessible from the master bedroom. Explore nearby hiking trails, discover hidden messages throughout the space, and enjoy a curated "meaningful library." Perfect for relaxation, adventure, and meaningful moments with loved ones.

Catskills cabin over waterfall w/ views & hot tub

Experience total privacy and relaxation in our magical log cabin on 10 acres of woods, 90-minutes from NYC! Our home sits atop a bedrock cliff, with gorgeous, untouched Shawangunk mountain views and the peaceful sounds of the river and 30-ft. waterfall running below. The cabin is wonderfully cozy yet spacious, rustic while having most modern amenities provided to you. Enjoy total seclusion close to so many things to see and do....best of both worlds!

Good Vibes Studio in the Woods

Relax in our peaceful studio featuring a memory foam queen bed and a futon—perfect for a quiet getaway or a fun weekend near top attractions. Just minutes from Bethel Woods, Resorts World Casino, Kartrite Waterpark, and White Lake dining. Surrounded by nature, with hosts next door if you need anything!

Appalachian Lodge Top Floor w/views

Welcome to our condo at The Appalachian! Fully furnished mountain side unit that has all the amenities and luxuries that you need for your stay and getaway. Enjoy in/out skiing, water park, and great local attractions.

Country Cabin on 115 acres Cabin #2, with WiFi

Charming Country Cabin 115 Acres with nature trails and private seclusion, short walk to the Private lakefront access, walking distance to local Pubs and Restaurants, a beautiful country setting