Cottage holiday rentals in Olive

Catskills Getaway w/AC on 3 Acres near Woodstock

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

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.

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.

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

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.

Stone House 1807. Comfort, Peace and Nature.

Historic 200 yr old stone cottage, on three floors, renovated to a high standard, creating a very comfortable and peaceful retreat, whilst retaining soul and character. Extreme cleanliness is a priority. Quality bedding assures a good nights sleep. The bathroom offers a rain shower and soaking tub. The kitchen is fully equipped and fresh produce is available from the neighboring organic farm in season. Good hiking trails are accessible from the house.

Leggett Cottage

Located in historic High Falls on Leggett Road, one of the loveliest roads in the area, is your private cottage. Just renovated, it has all new amenities. The location is steps away from the rail trail where you can bike or walk. Stone Ridge and High Falls are a half-mile away for all your shopping. Situated between the majestic Shawangunks and the Catskills; outdoor activities, farm to table restaurants, breweries and farmers markets abound.

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

Grapevine Cottage

DESCRIPTION Enter our private backyard on 2 1/2 acres by crossing your own bridge far above the forest floor overlooking a stream and waterfall, then meander along a stone path, entering your grape arbor and vegetable garden into your cottage. The gardens where featured in THE Wall Street JOURNAL Sept 11-12 2021

Lakefront House w/Private Dock, Fire Pit & Hot Tub

Cozy and recently renovated 1940s lakefront house right on the water. Enjoy views of the lake all around the house. Private dock, fire pit, and cedar hot tub. Under 2 hours from NYC, and 20 minutes to nearby shopping and restaurants as well as great hiking trails. High speed Internet and TV provided.