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House vacation rentals in Olive

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Top-rated house rentals in Olive

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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, 356 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.

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, 112 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 😊

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

4.98 out of 5 average rating, 152 reviews

Fall Special: Relax, BBQ, Save, 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

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, 289 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.

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, 236 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.

A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.

4.96 out of 5 average rating, 170 reviews

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

4.97 out of 5 average rating, 112 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

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, 149 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.

4.97 out of 5 average rating, 134 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.

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, 376 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

Home in Woodstock

4.99 out of 5 average rating, 122 reviews

Fall Fantasy Getaway

This Fall enjoy the changing foliage in your own private forest at the Maverick. As featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCentury deck home furnished with Eames and other iconic era furnishings. The Maverick is secluded yet just 5 minutes from downtown Woodstock as well as beautiful hiking, running, and biking trails. The home is perfectly set up for indoor | outdoor entertainment & dining.

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, 120 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

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Olive house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 505 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

An aerial view captures the sprawling property, surrounded by lush trees. The heated salt-water pool is visible, framed by a wooden deck and lounge chairs. A spacious outdoor deck with seating and a fire pit enhances the inviting outdoor space.

Home in Woodstock

4.86 out of 5 average rating, 216 reviews

Spacious Woodstock Haven Pool, Fire Pit, Nature

A modern farmhouse exterior is visible beside a crystal-clear swimming pool surrounded by grassy areas. Colorful pool floats are placed in the water, while a wooden fence and tall trees frame the peaceful setting.

Home in Saugerties

4.95 out of 5 average rating, 109 reviews

MODERN FARMHOUSE in the WOODS

Top guest favorite

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

Home in Saugerties

4.99 out of 5 average rating, 103 reviews

Woodstock Retreat- Heated Pool/Hot Tub/FirePit

Top guest favorite

An open living space features a grand piano positioned near large windows that offer views of the surrounding mountains. A light-colored sectional sofa and a round coffee table create a comfortable seating area, accented by a dining table beside it. Natural wood beams add architectural interest.

Home in Saugerties

5 out of 5 average rating, 153 reviews

Upstate Modern Scandinavian Barn in the Catskills

Top guest favorite

A tranquil in-ground pool is framed by lush greenery and vibrant flowers. Sun loungers and umbrellas line the poolside, offering shaded seating areas. Clear water reflects the surrounding trees and sunlight, creating a serene atmosphere for relaxation and recreation.

Home in High Falls

4.98 out of 5 average rating, 109 reviews

Cozy & Spacious Country Home - All Seasons

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

4.91 out of 5 average rating, 105 reviews

Curl Up & Relax - Cozy Stylish Stay nr Woodstock

An in-ground pool is situated amidst a lush green landscape, surrounded by tall grass and shrubs. The house, a charming two-story structure, is visible in the background, framed by gentle hills under a pastel sky. Outdoor seating and umbrellas are arranged nearby.

Home in Grahamsville

4.9 out of 5 average rating, 105 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

Weekly house rentals

Top guest favorite

The guest house features a contemporary exterior with green paneling and wooden accents. An extensive patio surrounds the structure, furnished with lounge chairs and a dining set. Large glass doors and windows invite natural light, while views of the surrounding landscape are visible.

Home in High Falls

5 out of 5 average rating, 239 reviews

Our Place - A Big Little House

Top guest favorite

The exterior of the retro-chic house is illuminated at night, highlighting its warm wooden facade and angular architectural lines. The outdoor patio features a stone pathway, dining area, and two blue chairs, creating a welcoming space surrounded by trees.

Home in Saugerties

4.97 out of 5 average rating, 233 reviews

Retro-Chic Cabin in Woodstock - Sauna

A small office nook features a gray sofa adorned with a textured throw pillow. A wooden desk with two chairs is positioned near a window, allowing natural light to brighten the space. A woven mirror and a framed art piece complete the design, enhancing the cozy atmosphere.

Home in Mount Tremper

4.93 out of 5 average rating, 289 reviews

Overlook Creek Cottage 1 Near Phoenicia

A two-story red cottage is nestled among tall trees, showcasing a classic design with multiple windows and balconies. A gravel driveway leads to the entrance, providing access to outdoor spaces. The surrounding wooded landscape adds to the cottage's natural setting.

Home in Bearsville

4.92 out of 5 average rating, 238 reviews

A Cozy’s Woodstock Getaway Home

An outdoor area is visible through a large window, featuring a vintage clawfoot bathtub and a wooden stool. A hammock is suspended nearby. Lush greenery surrounds the space, creating a serene atmosphere.

Home in Spring Glen

4.98 out of 5 average rating, 200 reviews

Creekside cottage on 65 acres of land

A serene view of a flowing river bordered by smooth rocks and a grassy shoreline. Lush trees line the riverbank, with distant mountains visible under a soft, golden sunset. The tranquil scene invites leisurely walks along the water's edge.

Home in Mount Tremper

4.91 out of 5 average rating, 202 reviews

Rippleside Retreat - Stay and Relax

Top guest favorite

A bright interior corner features a piece of original wall art depicting a figure standing before a window. A stained glass door with intricate designs allows light to filter through, enhancing the soft green walls. A small potted plant on a modern stand adds a touch of greenery.

4.97 out of 5 average rating, 102 reviews

Private Retreat b/t Mohonk & Woodstock - Sleeps 8

Top guest favorite

The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.

Home in Woodstock

4.91 out of 5 average rating, 721 reviews

Dutch Touch Woodstock Cottage

Private house rentals

Top guest favorite

An outdoor fire pit is surrounded by wooden chairs, creating a cozy atmosphere for gatherings. The setting sun casts a warm glow over the home, visible in the background, with trees framing the scene and outdoor lighting enhancing the tranquil ambiance.

Home in Olivebridge

5 out of 5 average rating, 83 reviews

Olive Woods House - Catskills Mountain Views

Top guest favorite

Home in Kerhonkson

5 out of 5 average rating, 22 reviews

Hudson Valley Black Barn w/ Firepit + Fireplace

Top guest favorite

A two-story home is surrounded by lush greenery and trees, featuring a spacious front porch with a railing. The home’s light-colored exterior contrasts with the vibrant outdoor setting, providing a serene atmosphere. A well-maintained lawn leads to a natural area in the background.

Home in Olivebridge

4.99 out of 5 average rating, 67 reviews

Country Getaway with Mountain View

Top guest favorite

A vintage earthmoving machine is positioned on a gravel lot, showcasing rusted metal and worn paint. A hydraulic crane and digging bucket are visible, surrounded by lush green trees in the background. The sky features a mix of clouds with patches of blue.

Home in Olivebridge

4.92 out of 5 average rating, 12 reviews

The Earthmover Inn

Top guest favorite

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

Home in Saugerties

4.98 out of 5 average rating, 157 reviews

The Stone House

A spacious dining area with a round marble table is surrounded by modern black and white chairs. Large windows provide a clear view of a snowy landscape outside, with decorative light fixtures hanging from the ceiling, creating a bright and airy feel.

5 out of 5 average rating, 89 reviews

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

The living room features warm wooden floors and exposed beams, creating a cozy atmosphere. A spacious sofa is paired with a modern armchair and side table. A fireplace is flanked by shelves displaying books and decor, while a guitar rests against a wall.

Home in Kingston

4.97 out of 5 average rating, 39 reviews

NEW: Luxe Historical Style in Stone Ridge.

A spacious living area features floor-to-ceiling windows that frame a serene forest view. Minimalist wooden furniture, including two chairs and a large sofa, invite relaxation. A sleek fireplace adds warmth, while soft natural light brightens the room's contemporary design.

Home in Krumville

4.88 out of 5 average rating, 8 reviews

Bluestone Cove - Modern Escape in the Woods

Quick stats about house rentals in Olive

Total rentals
110 properties
Nightly prices starting at
R522 ZAR before taxes and fees
Total number of reviews
6.4K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore