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, 640 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.

Nov 19 – 26

€ 134 per night

Guest favorite

Home in West Shokan

4.99 out of 5 average rating, 104 reviews

Panoramic Mountain views w/ hot tub, mins to hike

Picturesque ranch house nestled in a valley w/ panoramic mountain views, our 3 bdrm, 2 bath is available for your next escape from the big city. Enjoy hiking, walking trails galore within 5 - 15 min of the house or skiing 30 min away. Work from "home" with mountain views and super fast wifi and end the night gazing at the stars from the hot tub then fall asleep in the luxurious king size bed. We are only 20 min from Woodstock and 30 min to the slopes. Not suitable for children under 8 nor pets.

May 20 – 27

€ 340 per night

Guest favorite

Home in Stone Ridge

4.93 out of 5 average rating, 215 reviews

School house in the woods! Spring 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

Oct 12 – 19

€ 234 per night

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 277 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.

Mar 23 – 30

€ 153 per night

Guest favorite

Home in Olivebridge

5.0 out of 5 average rating, 101 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

Jun 5 – 12

€ 433 per night

Guest favorite

Home in Kerhonkson

4.99 out of 5 average rating, 120 reviews

✔13acres ✔Dogs OK ✔100% Solar + Powerwall ✔229Mbps

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

Jul 22 – 29

€ 556 per night

Guest favorite

Home in West Shokan

4.92 out of 5 average rating, 333 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.

Jun 6 – 13

€ 298 per night

Guest favorite

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

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.

Sep 8 – 15

€ 622 per night

Guest favorite

Home in Kingston

4.96 out of 5 average rating, 258 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!

Jul 8 – 15

€ 169 per night

Guest favorite

Home in Mount Tremper

4.96 out of 5 average rating, 214 reviews

Overlook Creek Cottage 1 Near Phoenicia

Located on the Esopus, Overlook Creek Cottage is a newly renovated space including modern kitchen and bathroom amenities, mid century modern design with a Bohemian flair and proximity to destinations such as the town of Phoenicia, The Pines restaurant, Phoenicia Diner, Foxfire Mountain House, The Emerson Resort and Mt. Tremper Arts. Nearby to hiking trails and other towns such as Woodstock and Kingston as well as the Ashokan Reservoir.

Dec 28 – Jan 4

€ 167 per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 678 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Feb 28 – Mar 7

€ 129 per night

Guest favorite

Home in Accord

4.97 out of 5 average rating, 117 reviews

The Woods House, 40 secluded acres & speedy wifi!

Private, Secluded, Peaceful! If you’re looking for a rare experience, a week, month or weekend respite —The Woods House is for you! Enjoy the peace! Conveniently located outside the historic village of Stone Ridge, NY, in the Lyonsville, Accord area—close to High Falls, Rosendale, Woodstock, Kingston and New Paltz — yet set in 40 acres of forest, our House in the Woods is blissfully quiet and secluded.

Sep 30 – Oct 7

€ 206 per night