House vacation rentals in Olive

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Top-rated house rentals in Olive

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Guest favorite

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

4.94 out of 5 average rating, 338 reviews

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.

Guest favorite

The historic house is surrounded by lush greenery, with a deck featuring Adirondack chairs. A grassy yard leads up to the entrance, while trees provide natural shade. The white wooden exterior complements the tranquil setting, inviting relaxation in a peaceful environment.

Home in West Shokan

4.87 out of 5 average rating, 127 reviews

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

Top guest favorite

A peaceful landscape is captured, featuring rolling hills under a clear blue sky. Lush green fields transition into vibrant fall foliage, showcasing various trees. Subtle sunlight casts gentle shadows across the scene, enhancing the serene ambiance of the natural surroundings.

Home in Woodstock

4.99 out of 5 average rating, 104 reviews

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 😊

Guest favorite

A spacious backyard features a firepit surrounded by rock seating, with string lights softly illuminating the area. The modern farmhouse stands in the background, showcasing multiple windows and a welcoming porch, creating an inviting outdoor setting.

Home in Kerhonkson

4.99 out of 5 average rating, 144 reviews

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

Guest favorite

The entrance of the cottage is framed by lush greenery and vibrant foliage. A stone pathway leads to a welcoming front door, accentuated by an overhanging roof and outdoor lighting. The architectural details are complemented by the surrounding natural landscape.

Home in Kerhonkson

5 out of 5 average rating, 274 reviews

Cook House | Modern Cottage w/ Hot Tub & Fireplace

Featured in Vogue, Curbed, and Remodelista, Cook House is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature. Hosted by The Reset Club, a member of 1% for the Planet.

Guest favorite

A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.

Home in Mount Tremper

4.93 out of 5 average rating, 225 reviews

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.

Guest favorite

A charming historic farmhouse is nestled among tall trees, surrounded by colorful autumn foliage. The two-story structure features a sloped roof and a welcoming porch adorned with plants. Sunlight filters through the leaves, casting a warm glow on the home’s exterior.

Home in Boiceville

4.91 out of 5 average rating, 156 reviews

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.

Top guest favorite

A spacious wooden deck extends from the contemporary home, flanked by greenery. Two red Adirondack chairs invite relaxation, while large glass doors showcase the interior. The deck area is surrounded by lush plants and trees, emphasizing the natural setting.

Home in Stone Ridge

4.96 out of 5 average rating, 148 reviews

Secluded Oasis w/ Fire Place In Stone Ridge

Beautiful contemporary on one of the most prestigious & scenic roads in Stone Ridge.On 6 acres for privacy, our country escape has 3 bedrooms; including 1 primary ensuite bed/bath. The living room is filled with sunlight encompassing its cathedral ceilings with a fireplace for those chilly nights. Separate dining room can host up to 6 people. Screened In Porch is key for those bbq nights. We are dog friendly only as we are highly allergic to cats. There is a $75 pet fee per stay.

Top guest favorite

A spacious studio area features wooden beams above, with a large artwork displayed on the back wall. The floor is adorned with various rugs, and a kitchenette is visible, equipped with essential appliances. A chair is situated near a curtain-draped area, enhancing the room's functionality.

Home in Shokan

4.97 out of 5 average rating, 124 reviews

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.

Guest favorite

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

4.95 out of 5 average rating, 364 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Top guest favorite

A spacious living area is defined by warm wooden beams and a bright, airy ambiance. Comfortable seating arrangements include gray sofas and an ottoman, complemented by a patterned area rug. Natural light is filtered through multiple windows, creating an inviting space.

Home in Olivebridge

5 out of 5 average rating, 116 reviews

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

Guest favorite

A spacious dining area features a large wooden table surrounded by modern chairs. Natural light filters through expansive windows, illuminating the inviting space. Accents include a plant in a terracotta pot and a decorative light fixture above the table, enhancing the earthy aesthetic.

Home in Accord

4.96 out of 5 average rating, 141 reviews

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.