Family-friendly holiday rentals in Olive

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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

The Black Dymond A Private Streamside Cabin

A 2.5 hour drive from NYC to a serene, private, woodland, streamside home. This cabin sits on the very edge of the Catskill Mountains. It's cozy, modern, and minimalistic with a touch of rustic elegance. All new appliances with all the cooking necessities, a comfortable bed with large screen smart tv, excellent wifi service, a romantic gas-powered fireplace and the most private back deck away from the world to get lost for a weekend in the beauty of the woods.*Now offering mid-week price deals!

Woodstock Catskills Retreat~Sweet, Private & Views

❤️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 😊

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 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.

Coldbrook Cottage

Welcome to Coldbrook Cottage. Less than 2 miles from The Onteora Mountain House wedding venue. A great romantic get-a-way. All 5-STAR reviews. We offer the amenities of a great hotel suite, but totally private. It's on one of Woodstock's nicest roads for walking, jogging, and bicycling. Wilson State Park is across the street and we're surrounded by protected land. 8 minutes to Woodstock. 20 minutes to Kingston. 20 minutes to skiing . Check our reviews!

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

Designer Log Cabin Retreat on 6 Private Acres

Escape to a designer log cabin set on 6 private wooded acres in the heart of the Hudson Valley—located in Stone Ridge, just minutes from Mohonk , and some of the region’s best hiking, wineries, and waterfalls. Perfect for a romantic getaway, quiet reset, or work-from-home retreat, this space was intentionally designed for slowing down—without sacrificing comfort or convenience. IG:@griffithhousecabin

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

Hot Tub & Chic Catskills Woodstock Design Retreat

Little Willow is a newly-updated, three-bedroom cottage overlooking the mountains, designed as a cozy, handsomely-decorated launchpad for exploring the Catskills and Hudson River Valley. We now have a hot tub with mountain and sunset views! Check out our design feature in Domino Magazine. Town of Olive Permit: STR-22-13 Ulster Country Certificate of Authority: 10655

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.