House vacation rentals in Olive

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.

Beautiful farmhouse with Mountain View- HITS- AC

Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Perched on the water’s edge, you’ll look down from this bright, modern post at an expanse of winding river and broad tree-lined meadows. Let the mellow current and enveloping natural setting satisfy and soothe your senses. This special place is close to everything, making it an ideal launchpad to all the Hudson Valley has to offer. Kingston, New Paltz and Rosendale are all ten minutes away, surrounding you with a plethora of hiking trails, climbing, dining, drinking, entertainment and shopping.

*superhost:)* School house in the woods!

This charming 1800s former one-room schoolhouse is now a cozy and comfortable 2 bedroom + Loft, 1 bathroom home available for short term rentals. Situated in a rural forested setting, but close to town and the best restaurants, farms, hikes, and swimming spots! *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

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Mt. Wonder: Cozy Cabin w/ Hot Tub and Wow View

Welcome to the Wonder of the Catskills. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Just 10 min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub & an overall magical feel. Amenities galore incl the tub, BBQ, firepit, wood stove & stocked kitchen. Peruse our books, vibe in nature or enjoy hikes & cute towns nearby.

Stony Clove Cottage - sleeps 6, *maximum 4 adults*

Welcome! Stony Clove Cottage sleeps a maximum 4 adults and 2 children. There are 2 queen beds and a bunkbed for children only. Located in the beautiful Catskill Mountains just 2 hours 15 mins. from NYC. Two great ski mountains, Hunter and Belleayre, are each 15 minutes away. Close to amazing hiking trails. Listen to the sound of the Stony Clove Creek and enjoy being in nature, while just 1 mile from Phoenicia's Main Street. Beautiful in all seasons! Shandaken STR License # 2023-STR-AO-059

West Wing - a unique private space w/deck

This unique studio space with private entrance is a recent addition to our charming home, located on a quiet private road in the village of Shokan. Situated within minutes of the Ashokan Rail Trail, this bike and walking trail offers dramatic vistas of the Ashokan Reservoir. Woodstock & Phoencia with their stores, galleries and restaurants are only 15 minute drives . Local recreation includes hiking trails, kayaking and for those looking for relaxation there are renowned spas.

HEAVEN ON EARTH - Hudson Riverfront Home

Voted #3 Most Romantic AirBnB Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Our Place - A Big Little House

Mahali Petu is a five year old guest house situated well off the road with meadow views. It is built of high quality materials and finishes. The kitchen is fully equipped and offers custom cabinetry & granite countertops. The full bath offers a walk-in European shower with dual shower heads. There is extensive outdoor decking with seating, a gas grill, fire pit, hot tub and an outdoor shower. Peaceful and quiet, yet walking distance to High Falls restaurants and shops.

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

Art Studio in the Gunks | Sauna + Forest Views

A peaceful forest retreat handcrafted by local artists. This spacious studio features a custom stone fireplace, original art, a handmade dining table, and a huge window overlooking the trees. Enjoy the private outdoor barrel sauna, bamboo floors, and a Casper mattress for deep rest. Perfect for hikers, creatives, and anyone needing to slow down and reconnect.