Pet-friendly holiday rentals in Olive

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.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Beautiful stream side cottage in the woods

Stunning fully renovated 1970 partial A frame cottage in the woods! Set privately on four acres with a stream and meandering stone walls, the cottage is modern yet rustic, with a mid century decor. Main floor has living room with beautiful floor to ceiling stone fireplace (gas operated), kitchen, bathroom, and an office with a desk and twin bed. Second floor has master bedroom with queen size bed and a separate loft area with desk. Great place to relax in nature - a perfect couple's getaway!

Stunning Passive Solar Cabin on 135 acres & pond

Just the perfect cabin. This newly built, passive solar house has a wood-burning stove, incredible views and is drenched with light. The house is intimate yet connected to the outside, with total seclusion and every imaginable modern convenience! It’s an architect-designed marvel of concrete, glass and reclaimed wood that sits on 135 acres of field and forest with a lovely swimming pond and miles of hiking trails. The cabin sleeps up to 6 people in two bedrooms and a spacious sleeping loft.

Rondout Rendezvous

Enjoy the historic Rondout district of Kingston while relaxing in this beautiful, one-bedroom, one bath unit on the first floor of a brick building from 1900. Historic charm meets modern amenities, with 12' ceilings, in-floor heating, and an open concept kitchen, living and dining area across the street from the Hideaway Marina on the Rondout Creek. Take a relaxing walk along the water to the historic waterfront area on Broadway for dining, shopping or a boat ride on the Hudson River.

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!

Shack in the Heart of Rosendale

This unique, centrally located 500 sq ft ground-floor, 1.5 story apartment is in an ideal location to explore Rosendale and the surrounding areas. Located in a 1890s Brownstone, the Shack is a comfortable refurbished studio with hand hewn beams, brick walls and a wood burning stove. Sleep in a queen Murphy bed (pulls down) and prepare food in the kitchenette. Keep in mind nobody above you and the town shuts down at 10 PM so you have a decent amount of peace and quiet.

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!

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.

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

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 on 40 acres of forest, our Woods House is blissfully quiet and secluded.