Vacation rentals with a patio in Olive

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Top-rated patio rentals in Olive

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Guest favorite

Cabin in Margaretville

4.93 out of 5 average rating, 158 reviews

Catskills Cabin Winter Oasis - Ski, Hike & More!

Welcome to our Catskills Cabin Nature Oasis, where you'll enjoy an old-fashioned Catskills stay in comfort and privacy in the heart of Balsam Lake Mountain, surrounded by an abundance of natural beauty, right near the quaint village of Margaretville. SECONDS from hiking trails, and MINUTES from skiing, canoeing, kayaking, and Village shops and eateries, our cozy cabin is equipped with a dynamic kitchen, wood stove, wrap around deck, screened-in porch, grill, fire pit, heat/AC, Smart TV, & more!

Guest favorite

Cabin in Big Indian

4.99 out of 5 average rating, 172 reviews

Slide Mountain Chalet

Welcome to Slide Mountain Chalet! Slide Mountain is the highest peak in the Catskills and this chalet is at an elevation of 2,100 ft! Enjoy 2 acres of beautiful moss-covered Hemlock forest on the property, which is located on one of the most scenic drives through the Catskills. Stargaze on the front porch, listen for one of the several species of owls, hang out by the firepit in the back yard nestled amongst large boulders, or fish the Neversink River for some of the best Trout in the Country!

Guest favorite

Home in Woodbourne

4.95 out of 5 average rating, 116 reviews

Cozy Catskills Cabin with Grill & Fire Pit

My cabin in rural, woodsy Catskills is perfect for a relaxing getaway/escape from the city. Read a book or binge a show in the cozy living room, cook an elaborate (or simple) meal in the big, recently renovated kitchen, grill and/or enjoy the fire pit on the patio, & get out in nature with hikes, a lake, & slopes nearby! 25 minutes to all the cute Catskills towns like Livingston Manor, Mountain Dale, & Ellenville with great restaurants, bars, and shops! Also, only 5 minutes from Hemlock spa!

Guest favorite

Cabin in Tannersville

4.98 out of 5 average rating, 197 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Guest favorite

Home in Woodstock

4.92 out of 5 average rating, 129 reviews

Serene Retreat w/ Cedar Hot Tub & Fire Pit

Whether you’re planning a couples getaway, a trip with friends, a family vacation, or even a solo escape, The Woodstock Retreat is your home away from home in the Catskills. Located just 5 mins from Woodstock, 10 mins from Saugerties, and surrounded by endless dining, shopping, and outdoor activities. Two separate bungalows, a handmade cedar hot tub, fire pit w/ Adirondack chairs, and hammocks are just a few of the features that make The Woodstock Retreat special. IG: @thewoodstockretreat

Guest favorite

Cabin in Accord

5 out of 5 average rating, 144 reviews

Modern Cabin with Stunning Pastoral+Mountain Views

Enjoy all the peaceful nature that the Hudson Valley has to offer while being centrally located to all the trendiest spots in the area! It's all in the details at our two bedroom + two bathroom, newly renovated home with cozy wood stove fireplace, stylish furniture, and farm + mountain views. 1400 sq ft, bright, airy, filled with plants, a comprehensive kitchen, farmhouse dining table, high-speed mesh wifi, smart TV with access to all the best streaming platforms, and a luxe freestanding tub.

Guest favorite

Bungalow in Big Indian

4.94 out of 5 average rating, 148 reviews

The Den @ Oliverea - Minutes to Hiking and Skiing!

Nestled into a quiet through road that goes to some of the best hiking nearby (hello Slide Mt.!) and just 10 minutes away from skiing at powder-coated Belleayre, my charming little two bedroom cottage is ready for your family or group's adventures. There is no cell service here, but fast Internet awaits the remote worker, with a modern mesh network providing indoor/outdoor coverage. Comfy beds, a stocked kitchen, a hot shower, and mountain peace await! Shandaken STR License #2022-STR-001P

Guest favorite

Home in Livingston Manor

4.94 out of 5 average rating, 121 reviews

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

Guest favorite

Cabin in Boiceville

4.96 out of 5 average rating, 144 reviews

Catskills Cabin Surrounded by Mountain Views+Spa!

Location is Everything! Our 3BR Catskills home is surrounded by breathtaking mountain views, and close to all including Woodstock Village, Phoenicia, Rivers, Hikes, Breweries, Ski Areas and more. Home is set high on a ridge overlooking nature from all angles on 3 private acres of land. Enormous brand new deck facing mountains with fire pit, grills. Perfect location for exploration. Tastefully decorated with brand new beds and furniture, fully stocked kitchen. Town of Olive STR-22-12.

Guest favorite

Home in Hunter

4.99 out of 5 average rating, 106 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!

Guest favorite

Guesthouse in Kerhonkson

4.88 out of 5 average rating, 103 reviews

Cozy Catskills Cottage

Welcome to our cottage! We have 4.5 acres in the Catskills which includes a cozy cottage overlooking a babbling brook and next to a adorable duck pond. Come for peace, privacy, and relaxation that's only 2 hours from NYC. Cottage, 1 Bedroom, two floors, 800 sq. ft., full bath, fully furnished with a deck and patio furniture. Set back in the woods on a shared property off a beautiful farm road in Kerhonkson. 10 minutes away from the Shawangunk mountains and amazing options for hikes.

Guest favorite

Vacation home in Shandaken

4.97 out of 5 average rating, 142 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Take it easy at this tranquil getaway while you see and hear only the water flow with wrap around 4 season river right off porch. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cats.