Pet-friendly vacation rentals in Olive

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.

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.

Newly built apartment steps from Mohonk preserve.

Nestled amongst the trees below Bonticou Crag this is a great base camp for climbing, hiking and biking. Five minutes from New Paltz; I do recommend having a car to access the area. Shared yard and fire pit right outside. My family and I live in the main part of the house. The outside area and house are still under construction, I’m working on it but its not put together yet. The apartment and inside area are clean and newly built with their own mini split and air circulation.

Dog Friendly Uptown Apt Near Stockade + Backyard

2 hours from NYC, escape to this pet-friendly outdoor oasis in Uptown Kingston only a short walk from the Historic Stockade District. Renovated in 2020, this 1-bedroom apartment is accented with vintage decor, indoor plants and has a huge backyard for your pup. Use the full kitchen or walk to the many restaurants in the Stockade. The expansive backyard includes a stone patio, outdoor table for dining, Adirondack chairs & hammock. Free driveway parking, WIFI, and Netflix!

Modern Cabin Getaway: Idyllic, Secluded, Serene

Escape to our charming log cabin, nestled on a serene 6-acre property surrounded by the soothing sounds of nature and scenic beauty. Though perfectly private, the cabin is conveniently located near markets, shops, restaurants, and just a short distance to the heart of town. An ideal escape Less than 2hrs from NYC. Hiking, nature trails, swimming holes, skiing, local farms, wineries, reservoirs, waterfalls, historic sites, all await you. IG:@griffithhousecabin

Hudson Valley Hygge House~ comfort in the country!

Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

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

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

Cozy 1-bedroom log cabin in the mountains

Take it easy at this comfortable and tranquil getaway. This sweet little log cabin for two is nestled in some of the most dramatic peaks in New York State. We are quick hop to Slide Mountain, Giant Ledge, and many other trailheads. We are within 20 minutes of Frost Valley YMCA, Peekamoose Restaurant, Belleayre ski hills, and Phoenicia. This cabin is a perfect home base for outdoor adventure, and also a peaceful respite.

ENTER HOME - Minimalistic style warm & inviting

ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only

Hot Tub & Chic Catskills Woodstock Design Retreat

Little Willow is a newly-updated, three-bedroom cottage overlooking the mountains, designed as a cozy, handsomely-decorated launchpad for exploring the Catskills and Hudson River Valley. We now have a hot tub with mountain and sunset views! Check out our design feature in Domino Magazine. Town of Olive Permit: STR-22-13 Ulster Country Certificate of Authority: 10655

Whimsical Woodland Cottage in Stone Ridge NY

This adorable cottage features an indoor fireplace, loft, screened in porch, outdoor fire pit and outdoor deck. It is tucked away from the road yet only minutes to town. Centrally located you can get to all the towns in the Catskills quickly. Plenty to do like hiking, apple picking, antiquing and shopping. This cottage is the perfect retreat from the city.