Vacation 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!

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 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.

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

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

Private Retreat b/t Mohonk & Woodstock - Sleeps 8

Come enjoy our mountain retreat! This secluded 3000-square-foot craftsman home sits on 5.5 wooded acres set far off of a quiet road in Accord. There are three large bedrooms with queen beds (all brand new top-of-the-line memory foam) and a media room with a door that has a queen pull out couch. Additionally, there are two twin XL rollaway beds (also memory foam) for your use. All in all, the house comfortably sleeps 8.

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.