House holiday rentals in Olive

Stream-side Home, Quiet, Peaceful & Secluded

Stream side, Historic 3 Bedroom Home near Woodstock, Phoenicia, Hunter and Belleayre Ski Centers. Available for seasonal, week & weekend rental with 2 Baths, Living Room, Dining Room, Eat in Kitchen, Woods, Fire Place, Burn Pit, 51" TV, 15' x 30' Deck, High Speed Internet, Great Cell Service, large yard, large hill, nicely secluded. We have Adirondack Reclining Chairs on 3 acres of property. The home is quiet & Peaceful next to Dry Brook surrounded by The Catskill Mountains. Cert. STR-23-24

Woodstock Catskill Escape: Bright Views & Private

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, and Phoenicia, Saugerties, ski resorts and many outdoor adventures & various 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 😊

BBQ & Starlight, 13 acres, 100% Solar + Powerwall.

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

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View

Welcome to the most splendid view in the Catskills. With a private outdoor spa. And just 10 min to Woodstock. This secluded cabin sits on 18 acres w/ private creek access & forest. Seeking a vacation w friends or a romantic escape? This is the place. Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub, sauna & cold plunge Amenities galore incl the spa, BBQ, firepit, games, wood stove & stocked kitchen. Peruse our books, be in nature or enjoy hikes & towns. This is the one.

Charming and Secluded 1840 Farmhouse

Charming, historic home on 5 wooded acres. Peace, tranquility, mtn. views, American antiques, wood-burning F/P. 3 BRs, 2 full baths, fully-equip. kitchen, wash/dryer, living rm, dining rm, library. IGA & Bread Alone mns away. WiFi/noTV. A/C in Master BR only. New patio with new outdoor grill and string lights. Toddlers not recom. All guests aged 2+ must be included in initial reservation #; more than two guests, add $35 per person per day. Use of piano+$75. Recyl vital. No smoking/no pets.

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.

Olive Outpost: Catskills 3BR House on Private Road

Welcome to the Olive Outpost! (@oliveoutpost) Our light-filled, 1,600 SF, 3-bed, 2-bath house is on 32 acres off a private road. We're close to the towns of High Falls, Stone Ridge & Accord (15 mins), Woodstock, Phoenicia (25 mins) & Kingston (30 mins). Note: This house is ~200 ft from the meadow cabin where the owners or guests may be; each has separate driveways and outdoor spaces. Photos courtesy of @nicoschinco. Town of Olive STR Reg #: STR-22-6

Little Minka - Japanese House in the Woods

Little Minka. A serene Japanese folk house nestled on 10 acres of private woodland and streams. Embracing the Wabi-Sabi, Little Minka is unique, handcrafted using Japanese traditional carpentry joinery methods. Soaring ceilings, shoji, and tatami complete the interior. Outside there's a fire pit, open cooking area. We have a wood fired hot tub on request. We have Japanese bathroom products in partnership with sowakanyc that guests can experience.

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.