Pet-friendly holiday rentals in Olive

Catskills Mountain River Dream House

*Art-filled c. 1910 Cottage w/ wrap-around porch *Self-contained natural wonderland for grownups, kids, & dogs *Riverfront w/ amazing swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, classic tree swing, & surrounding woods *Speedminton court *Mature perennial butterfly gardens *Fire pit *Weber Gas Grill *Cedar hot outdoor rain shower nestled in side garden *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll); 2 adult bikes

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!

Top 5% - Private & Modern Farmhouse, BBQ, 2hrs NYC

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

6 Private, Serene Acres, Firepit, Screened Porch

Unplug, unwind, and reconnect with nature at our peaceful log cabin on 6 private wooded acres in historic Stone Ridge. Less than two hours from Manhattan and minutes from Mohonk Preserve, Minnewaska, the Gunks, hiking, waterfalls, wineries, restaurants, and local farms. Perfect for romantic getaways, peaceful resets, and outdoor adventures, this thoughtfully designed retreat offers comfort, privacy, and room to breathe, slow mornings and cozy nights. IG:@Stillwood_Retreat

Historic Schoolhouse | Outdoor Shower + Pets OK!

Stay in a charming 1800s schoolhouse tucked into the woods in Stone Ridge. With two bedrooms, plus a private sleeping loft, a wood-burning stove, and modern amenities, it’s a cozy home base for exploring the Hudson Valley and Catskills. *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

Contemporary Stone Ridge Retreat | 6 Private Acres

Escape to the Hudson Valley in this bright contemporary retreat on 6 private acres along one of Stone Ridge's most scenic roads. This single-level home offers 3 bedrooms, including a primary ensuite, cathedral ceilings, a wood-burning fireplace, screened porch, fire pit, and thoughtful luxury touches throughout. Minutes from hiking, farm stands, restaurants, and charming Hudson Valley towns. Dog friendly ($125 fee per dog; no cats due to allergies). STR 2025-01

A Very Cozy House With a Very Big Yard

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

ENTER HOME - Minimalistic style warm & inviting

ENTER our HOME, an inviting, comfortable space filled with natural light and clean lines inspired by Nordic design. Enjoy a fully equipped new kitchen with Bosch appliances, including a washer and dryer. Our home is designed to embrace the beautiful nature around you and bring a sense of peace and comfort to your stay. ENTER HOME is ideal for individuals, couples, or families with children. AC is provided in both bedrooms only.

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

Historic Catskills farmhouse with sweeping views

Welcome to Juniper Grove - your country home in the Catskills. This 4 bed 2 full/2 half bath farmhouse has stunning views of the Ashokan Reservoir to enjoy from the classic farmhouse front porch. Relax under the stars in the new hot tub on the back stone patio. Sitting on 40 private acres, you are held by Mother Nature at every turn. Inside find all the modern conveniences & comforts to support your stay.

Catskills Woodstock Design Retreat w/ hot tub

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

The Cottage

Located just a short drive north of NYC, nestled between Woodstock and Phonecia, is a little cottage waiting to be discovered by you or you and a guest! This is a stand-alone cottage apart from the main house on the property with its own designated parking, so you get this entire private oasis to yourself.