Cottage holiday rentals in Olive

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 Country Cottage

Dogs welcome with no pet fee! Come relax at this adorable cottage in upstate NY, at the foot of the Catskills! Sweet 2 bdrm, 1 bath home centrally located in Kerhonkson, close to Mohonk and Minnewaska. Enjoy our private deck with spacious views towards the Rondout Valley and the Catskills, and a large fenced in yard, great for pets. If you are looking for a peaceful escape still convenient to all the great activities in the Hudson Valley has to offer, this is it. We are 2 hrs by car from NYC.

Contemporary Guesthouse with Heated Pool

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

Cozy Cottage with Stunning Mountain Views

Welcome to Halcott Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

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.

Coldbrook Cottage

Welcome to Coldbrook Cottage. Less than 2 miles from The Onteora Mountain House wedding venue. A great romantic get-a-way. All 5-STAR reviews. We offer the amenities of a great hotel suite, but totally private. It's on one of Woodstock's nicest roads for walking, jogging, and bicycling. Wilson State Park is across the street and we're surrounded by protected land. 8 minutes to Woodstock. 20 minutes to Kingston. 20 minutes to skiing . Check our reviews!

Perch Cottages #9: 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

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Stay at our comfortable and private 2-bed/2-bath home with covered porch, hot tub, fire pit, outdoor shower, and additional office cabin (perfect for work, exercise, or meditation) all surrounded by beautifully wooded forest. Centrally located in Kerhonkson just 15 minutes from local farm markets, popular farm-to-table restaurants and breweries, and hiking and other outdoor activities.

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

Hidden Gem Cottage — cozy escape to play or WFH

Brand new open concept cottage with sleeping loft and kitchenette*......enjoy the privacy and quiet of your own indoor and outdoor space. Surrounded by nature and adorable towns within 20 minutes. Come to relax and recharge . We want you to feel how we feel wrapped in comfort, quiet and nature *enough small appliances to cook in the space.

The Hickory Cottage - perfect!

Sweet new 2 bedroom cottage in Accord NY. Located in a quiet country setting, this home is light and bright with lots of sunny windows. The cottage has a huge deck with charcoal BBQ grill, and a fire pit. Minutes to Stone Ridge or High Falls. Close to Inness, Westwind Orchard, and Arrowood Brewery. Very Special.