House vacation rentals in Olive

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Top-rated house rentals in Olive

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Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 673 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Guest favorite

Home in West Shokan

4.86 out of 5 average rating, 125 reviews

Quiet, Peaceful & Secluded Streamside House,

Historic 3 Bedroom House 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, Stream, 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 house is quiet & Peaceful next to Dry Brook surrounded by The Catskill Mountains.Certificate STR-23-24

Guest favorite

Home in Stone Ridge

4.89 out of 5 average rating, 232 reviews

School house in the woods! Holiday dates added

This charming 1800s former one-room schoolhouse is now a cozy and comfortable 2 bedroom + Loft, 1 bathroom home available for short term rentals. Situated in a rural forested setting, but close to town and the best restaurants, farms, hikes, and swimming spots! *Pet friendly (no fee!) *WFH (Strong/reliable wifi!) *Family-friendly (high-chair and Pack n Play for babies, games/toys for kids!) ***Ask about adding a chef-prepared family-style dinner at the neighbor's farm @StoneRidgeSchoolhouse

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 317 reviews

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Guest favorite

Home in Olivebridge

5 out of 5 average rating, 113 reviews

Olive Outpost: Catskills 3BR House on Private Road

Welcome to the Olive Outpost in The Catskills! (@oliveoutpost) Our light-filled, 1,600 SF, 3-bed, 2-bath house is on 32 acres off a private road and ideal for a small group (6 or under). We're close to the towns of High Falls, Stone Ridge & Accord (15 mins), Woodstock, Phoenicia (25 mins) & Kingston (30 mins). NOTE: There is a guest cabin on the property where the owners may be staying (or available for additional capacity) Photos courtesy of @nicoschinco Town of Olive STR Reg #: STR-22-6

Guest favorite

Home in Kerhonkson

4.99 out of 5 average rating, 135 reviews

13 acres - Dogs OK - 100% Solar + Powerwall - BBQ!

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

Home in Kerhonkson

5 out of 5 average rating, 243 reviews

Cook House | Modern Cottage w/ 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 chopping veggies while records spin across the Sonos speakers. Eat al fresco on the porch and retire with a luxurious bath and your favorite streaming show on the drop-down projection screen at the foot of the bed. Great for couples or individuals looking to relax, cook, work, and enjoy nature.

Guest favorite

Home in Stone Ridge

4.96 out of 5 average rating, 134 reviews

Secluded Oasis w/ Screened Porch 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.

Guest favorite

Home in West Shokan

4.92 out of 5 average rating, 345 reviews

1850 Carriage House, Creek

Sunny Carriage House near the Ashokan Rail Trail and Catskill high peaks, with the beautiful sound of the nearby Bushkill Creek. Spacious, clean, peaceful. Fast reliable WIFI, woodstove. Two bedrooms, marble bathroom, AC, fire pit. A comfortable mix of handmade wooden mid-century minimalism. The house is in a beautiful natural setting while a short drive to town, restaurants. If The Carriage House is booked for your dates, check out Watson House, a 150-year-old house next door.

Guest favorite

Home in Kerhonkson

4.95 out of 5 average rating, 345 reviews

Cozy Country Cabin for Dogs, Families & Friends

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.

Guest favorite

Home in Woodstock

4.99 out of 5 average rating, 100 reviews

Sweet bright Woodstock getaway w. 3 acre privacy

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, and Phoenicia, Saugerties, Hunter ski resort and many outdoor adventures & restaurants nearby. 🥾 PinkyHouse, where friends and family gather for a fun 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. You’ll enjoy your relaxing getaway here! 😊 * Sorry, No Pets & No-smoking

Guest favorite

Home in Kingston

4.96 out of 5 average rating, 286 reviews

Country Elegance with Beautiful Catskill Mt. Views

Great location, 20 minutes from Woodstock, Kingston, Stone Ridge, High Falls. 2 hours north of New York City. Located on a cul-de-sac with an incredible view of High Point Mt. with breathtaking sunsets minutes from the Ashokan Reservoir! We supply wood for the wood-burning stove + baseboard heat. We have Apple TV, Espresso coffee machine, French Press, Pour-Over, Blender, Magic Bullet, Food Processor and Toaster Oven. People from all backgrounds are welcome! Eco-friendly!