Family-friendly holiday rentals in Olive

Catskills Getaway w/AC on 3 Acres near Woodstock

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

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

Studio in Private Forest; Peace and Solitude

Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

Beautiful stream side cottage in the woods

Stunning fully renovated 1970 partial A frame cottage in the woods! Set privately on four acres with a stream and meandering stone walls, the cottage is modern yet rustic, with a mid century decor. Main floor has living room with beautiful floor to ceiling stone fireplace (gas operated), kitchen, bathroom, and an office with a desk and twin bed. Second floor has master bedroom with queen size bed and a separate loft area with desk. Great place to relax in nature - a perfect couple's getaway!

Cabin 192

No cleaning fee and no 2-night minimum! Cabin 192 is a tiny home glamping experience located in lovely Kingston, NY. Cabin 192 takes you back to 1992 with: a vhs collection of classics, a Super Nintendo, Sega, and other fun activities. Warm and toasty in fall and winter and cool in summer you’re always comfortable at Cabin 192. Enjoy smores by the fire surrounded by trees in nature while also being able to enjoy a vibrant uptown district a 9-minute drive away! Minnewaska and Woodstock nearby!

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

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.

West Wing - a unique private space w/deck

This unique studio space with private entrance is a recent addition to our charming home, located on a quiet private road in the village of Shokan. Situated within minutes of the Ashokan Rail Trail, this bike and walking trail offers dramatic vistas of the Ashokan Reservoir. Woodstock & Phoencia with their stores, galleries and restaurants are only 15 minute drives . Local recreation includes hiking trails, kayaking and for those looking for relaxation there are renowned spas.

Canyon Edge off - grid Bungalow

The ideal perch to reflect, connect, and participate in nature's beauty. This unique structure blends pure nature with simple comfort. Sitting canyon side, you sleep beneath the canopy and wake to the mountains of the Hudson Valley. Welcome the spring buds of our forest oaks; Make summertime memories into the night by the fireside; Enjoy natures fall masterpiece of changing of the leave; Reflect on the year as the snowflakes fall Read listing fully, we’re available for any Q’s!

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.

Woodland Neighborhood Retreat

Relax in a cozy studio in the peaceful woods. Tasteful high-quality touches will have you feeling comfortable right away! This is an ideal space for up to 2 adults and up to 2 children. We live upstairs & offer self-check-in. A rare find in the Hudson Valley, our neighborhood is mostly flat, with walkable, quiet roads, and excellent bird-watching. It's an easy bike ride to connect to the vast state-wide rail trail system & all that the Mohonk Preserve has to offer.