House vacation rentals in Olive

Accord River House

Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.

Value · Location · Hiking

*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

Value · Family · Quiet

The Upstate Creek House

Built in late 1700, this modern Farmhouse on a creek is peaceful. You will see the original bones of the house through some of the lower ceilings & doorways on the 1st floor which gives this gem uniqueness. Lots of beautiful natural light. 200+ sq.ft screen enclosed porch, wood stove, outdoor fire pit, updated kitchen, 3 bdr & 2 bth, games-a-plenty, books-a plenty, & over 2,200+ sq.ft to enjoy. Positioned 90 minutes away from NYC, the house is central to everything you want to do in Upstate NY.

Family · Location · Bathroom

Woodstock Catskills Retreat~Sweet, Private & Views

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, Phoenicia, Saugerties, Hunter & Belleayre ski and many outdoor adventures & dining options nearby. 🥾 😊 PinkyHouse, where friends and family gather for a lovely time and fond memories, welcomes you to its bright, sweet, peaceful, and private setting on 3.5 acres of green & forest with a brook and view of mountains. Enjoy your relaxing getaway here! 😊 🥾🚙⛰️ * No Pets & No-smoking xoxox anne 😊

Value · Family · Checkout

Boulder Tree House

Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for an exciting, romantic, unique experience but can accommodate a 3rd person.

Location · Family · Indoor spaces

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

Value · Location · Nearby

Mt. Wonder: Big Cozy Cabin with Wow View

Welcome to Mt Wonder. With a wood burning hot tub, this quiet cabin perches on 18 acres with creek access, a vast forest & the greatest view in the county. 10 min to Woodstock. Seeking a vacation w friends or a romantic sojourn? Enjoy this rustic 2br 1ba cabin, cozy & spacious - a unique magical feel. Mega amenities incl the tub, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin's cabin called "Wonders Never Cease"

Location · Value · Access

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.

Family · Location · Comfort

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

Value · Family · Accuracy

Hudson Valley Hygge House~ comfort in the country!

Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

Family · Value · Decor

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

Value · Family · Biking

Private Retreat b/t Mohonk & Woodstock - Sleeps 8

Come enjoy our mountain retreat! This secluded 3000-square-foot craftsman home sits on 5.5 wooded acres set far off of a quiet road in Accord. There are three large bedrooms with queen beds (all brand new top-of-the-line memory foam) and a media room with a door that has a queen pull out couch. Additionally, there are two twin XL rollaway beds (also memory foam) for your use. All in all, the house comfortably sleeps 8.

Family · Location · Hospitality