Pet-friendly holiday rentals in Olive

Mt. Guardian Guest House Exquisite Mountain Views

Exquisite mountain views, immaculate cleanliness, cozy wood stove, beautifully designed, great bed, all amenities, freshly roasted coffee, well-equipped kitchen, excellent Wi-Fi, cable TV, Netflix, and serenity! Close to everything, far from everyone. AirBnB PLUS, Super Hosts, registered with town and county. We follow AirBnB Covid cleaning protocols and run a large HEPA air filter between guests. Pet friendly with prior permission. Over 500 exceptional reviews–many guests return again and again. Winter mid-week discount: book 3 or more nights (Sunday - Thursday) and get one night free! Our little cabin is made and furnished with great care and attention to detail. The space is comfortable and homey, bright and flooded with fresh mountain air. Many of the pieces are hand made and those that are not were chosen for both their aesthetic and functionality. We offer high speed internet access, full service internet TV, Netflix, and a full kitchen with every utensil and pot/pan you need (we've been to a bunch of airbnb's and we hardly ever saw a decent sized spaghetti pot!) and hand crafted bathroom with shower. The views from every window are exquisite - from the front we have miles and miles of national park that change in appearance every day. Whether its covered in fog, changing leaves, bright sunshine or fresh snow Mount Guardian delivers a constantly changing and stunning landscape. Enjoy your morning cup from one of the hammock chairs, the couch, or with a newspaper at the kitchen table... At night , forego the tech and curl up in front of the fire with one of our books, or set up a board game with a glass of wine. The place is cozy warm in the coldest months, and although we have air conditioning, its rare that you'll need it. When you're ready - jump into our queen sized memory foam bed before deciding to get one for yourself (yes - its that good and we're happy to share the details). and gaze up through the skylight at the stars. If you're used to sleeping with constant light and noise you'll be amazed at how well rested you feel after just a couple nights on the mountain. Skiers- we can't guarantee the snow, but the cabin is 20 miles from Hunter, 31 miles to Windham, and 36 miles to Belleayre. Inquire about our mid-week skier specials (Sunday night through Friday morning). We are pet friendly, but only small and medium sized dogs (sorry, we can't allow cats). We charge a cash deposit on arrival, and return it to you at the end of your stay. If you would like to bring a dog, PLEASE SEND AN INQUIRY (DO NOT USE INSTANT BOOKING). We have some pet guidelines which you need to read and agree to first. Nothing huge or surprising, but due to some irresponsible pet owners, we like to be clear before you book. If you are planning to come by motorcycle, PLEASE send an inquiry (do not use instant booking). Special Events in the area: June: Taste of Country and Mountain Jam at Hunter Mountain (Both are great by the way!) June through October: Usually something just about every weekend. Check out what is going on at Levon Helm Studios, Bearsville Theatre, the Colony, Maverick Concerts. Many other music and theater venues a little farther off. Mid October: The view of the changing leaves is spectacular Mid October: Woodstock Film Festival. Book early. This brings big crowds to our little town. Late October: Woodstock Luthier Festival November: Halloween in Woodstock is an event not to be missed. Half for the kids, half for all the folks around here who haven't abandoned their 8 year old. A LOT of fun. Christmas: when Santa comes to Woodstock, most of the town turns out for the welcome party. Like no other. We use a keypad system so you can check-in any time after 3:00pm. If you're coming from the city by bus (Trailways stops in Bearsville and Woodstock), you can get an Uber, Lyft, or a cab- but service can be pretty slow up here (there are only a few drivers.) The cabin is a good 45 minute walk from town, up a pretty good hill. We are generally nearby if you need anything. We also leave very explicit instructions for reaching us if there is an urgent need. The cottage is set in the secluded woods of Mt. Guardian, four miles from the center of Woodstock. Explore artist workshops and colonies, excellent music venues, great restaurants, bars, and plenty of cool little shops. Hiking, skiing, swimming, and tubing are all nearby. Licensed massage therapist available next door or in cabin (please book in advance). It's beautiful up here every season- spring and fall are magical, summer swimming, tubing, exploring and winter skiing and times by the fire. Around here it helps to have a car. Though you can do without one if you're staying in for the most part, the cabs in Woodstock are from Kingston and charge a rather serious call out fee. Uber/Lyft are now available, but you may wait a while to be picked up. As mentioned before Trailways bus service will drop you in Bearsville or Woodstock from the Port Authority and the Amtrak drops in Rhinecliff. Cabs are available at Rhinecliff station but your best bet is to rent a car or drive your own. In winter, the roads up here are plowed frequently. Our driveway is plowed and level, and is accessible to most vehicles throughout the year. We have a dog who lives on the property (next door) - he's very gentle and doesn't bark unless a critter alerts him - though we have a fair few of those up on the mountain! He is an indoor dog and unless you are around while he's being walked or chasing sticks, his presence shouldn't impact your stay. With prior approval, we are happy to welcome quiet well-mannered pets. We require an additional security deposit and provide a receipt and simple "pet deposit agreement" on check-in. We ask pet owners to follow our "pet rules" which include keeping your dog in a suitable pen if you are gone from the cabin. No pups on furniture or bed, pick up after your dog in the yard. You may want to bring a mat or blanket. We will provide full details regarding pets when we get your inquiry. You'll have good wifi in the cabin. Mobile service is great for Verizon, and very limited for other carriers.

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.

Peaceful Cottage-in Private 5-acre field

Modern cottage with large outdoor living area in a beautifully secluded 5-acre field. A quiet and romantic getaway centrally located to Arrowood Farms, Westward Orchard, Inness Resort & Golf, Butterfields, Ollie's, as well as local hiking including Minnewaska State Park and the Mohonk Mountain House. Escape to a calm and relaxing environment with updated amenities yet pet-friendly. Enjoy lounging and dining on the deck while watching the wildlife or simply roasting s'mores in the fire pit.

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

Cozy, Serene, Modern Cabin Escape

Escape to a cozy, modern log cabin nestled on 6 private, wooded acres. Designed for rest, reconnection, and comfort, this dog-friendly cabin offers total privacy with the convenience of being just minutes from town. Whether you’re planning a romantic weekend getaway, a peaceful work-from-home escape, or a nature-filled retreat, we invite you to slow down and unwind. You’ll feel worlds away from the noise, yet close to everything that makes the Hudson Valley special. IG:@griffithhousecabin

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Equipped with a backup generator. Dogs considered, just ask.

Fenced & Salt Water Pool | Cozy Catskills Cottage

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.

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

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

Perch Cottages #7: Creek access + Sauna + Mt views

A group of modern cottages with spectacular mountain views, and magical creek frontage on the Esopus Creek (with its own beach and swimming hole!) Completely renovated. Quick 2 HR drive from the City. ✔ Fishing and Swimming ✔ 1 Dog or Cat per cabin allowed ✔ Gas BBQ Grill ✔ 40” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Onsite parking 7 mins → Ashokan Rail Trail 25 mins → Belleayre Ski Resort

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