Family-friendly holiday rentals in Olive

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

Catskills Mountain River Dream House

*Art-filled c. 1910 Cottage w/ wrap-around porch *Self-contained natural wonderland for grownups, kids, & dogs *Riverfront w/ amazing swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, classic tree swing, & surrounding woods *Speedminton court *Mature perennial butterfly gardens *Fire pit *Weber Gas Grill *Cedar hot outdoor rain shower nestled in side garden *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll); 2 adult bikes

Catskills Woodstock Nature Retreat Views & Privacy

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, Phoenicia, Saugerties, Hunter & Belleayre ski and many outdoor adventures & dining options nearby. 🥾 😊 PinkyHouse, where friends and family gather for a lovely time and fond memories, welcomes you to its bright, sweet, peaceful, and private setting on 3.5 acres of green & forest with a brook and view of mountains. Enjoy your relaxing getaway here! 😊 🥾🚙⛰️ * No Pets & No-smoking xoxox anne 😊

Spring Special: Private Modern Farmhouse, 2hrs NYC

Super private, pet-friendly 13 acre solar powered*, modern farmhouse 2 hours from NYC in Catskills. ✔ Large backyard w/ firepit ✔ Dogs allowed** ✔ 229Mbps wifi ✔ Screen-in porch w/ outdoor dining ✔ 65” Smart TV with Apple TV in living room ✔ 50” Smart TV with Apple TV in guest bed ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Onsite parking 10 mins → Vernooy Falls 20 mins → Minnewaska State Park, Mohonk Preserve & Ashokan Rail Trail

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

The Metsämökki - A Finnish Cabin in the Woods

The Metsämökki is a small Finnish cabin in the foothills of the Catskill Mountains. Originally a sauna that was shipped here from Finland. We renovated it to a tiny house that offers complete privacy. Enjoy the babbling brook while sitting on the deck and taking in the surrounding nature. We're not offering high-tech or glamour but this cabin is a beautiful retreat from the busy city. **Check out our new midweek discounted rates and enjoy a little extra time for a great price!!

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Equipped with a backup generator. Dogs considered, just ask.

Cozy, Serene & Modern Cabin Escape

Escape to a cozy, modern log cabin nestled on 6 wooded acres. Designed for rest, relaxation, and comfort, the cabin offers privacy with the convenience of being just minutes from town. Whether you’re planning a romantic weekend getaway, a peaceful work-from-home escape, or a nature-filled retreat, we invite you to slow down and unwind. You’ll feel worlds away from the noise, yet close to everything that makes the Hudson Valley special. IG:@griffithhousecabin

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

ENTER HOME - Minimalistic style warm & inviting

ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only

The Cottage

Located just a short drive north of NYC, nestled between Woodstock and Phonecia, is a little cottage waiting to be discovered by you or you and a guest! This is a stand-alone cottage apart from the main house on the property with its own designated parking, so you get this entire private oasis to yourself.