
House vacation rentals in Olive
Find and book unique houses on Airbnb
Quick stats about house rentals in Olive

Total vacation rentals
Explore 100 vacation rentals in Olive

Nightly prices starting at
Olive vacation rentals start at G$14,624 GYD per night before taxes and fees

Verified guest reviews
Over 6,670 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
100 of Olive vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Olive rentals

4.9 Average rating
Olive stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Olive
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.
LocationFamilyAmenities

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.
ValueFamilyAmenities

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 😊
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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
ValueLocationSleep quality

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"
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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.
ValueFamilyCheck-in

Historic Schoolhouse | Outdoor Shower + Pets OK!
Stay in a charming 1800s schoolhouse tucked into the woods in Stone Ridge. With two bedrooms, plus a private sleeping loft, a wood-burning stove, and modern amenities, it’s a cozy home base for exploring the Hudson Valley and Catskills. *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
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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
LocationFamilyHospitality

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!
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A Very Cozy House With a Very Big Yard
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.
FamilyValueCheckout

ENTER HOME - Minimalistic style warm & inviting
ENTER our HOME, an inviting, comfortable space filled with natural light and clean lines inspired by Nordic design. Enjoy a fully equipped new kitchen with Bosch appliances, including a washer and dryer. Our home is designed to embrace the beautiful nature around you and bring a sense of peace and comfort to your stay. ENTER HOME is ideal for individuals, couples, or families with children. AC is provided in both bedrooms only.
LocationValueKitchen

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.
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Popular amenities for Olive house rentals
House rentals with a pool

Luxe modern A Frame, Hot tub and new heated pool
LocationFamilyPets

Spacious Catskills Farmhouse on over 5 acres!
ValueFamilyCondition

Woodstock Historic Artist Estate- The Museum House
FamilyLocationIndoor spaces

Private Countryside Retreat with Pool & Hot Tub
ValueLocationView

Summer Paradise - Pool, Fire-pit, Nursery!
LocationValueLong stay

Comfortable & Spacious Country Home - All Seasons
LocationFamilyWalkability

Scenic River View Escape | New Paltz
ValueFamilyCheck-in

4Br Mountain Brook House on 130 acres w/ trails
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Weekly house rentals

Charming and Secluded 1840 Farmhouse
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The Woods House, 40 secluded acres & speedy wifi!
FamilyLocationSleep quality

Chef's kitchen, seclusion, and breathtaking views
FamilyValueOutdoor spaces

Woodstock Hideaway
LocationFamilyWalkability

Architectural Private Gem w/ Views + Hot Tub
ValueLocationHeating

Little Minka - Japanese House in the Woods
ValueFamilyCondition

Fox Lodge: Hudson Valley / Catskills Getaway
FamilyLocationCleanliness

Modern House with Mountain View @Getawind
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Private house rentals

Catskills Hudson Valley Family Hideaway
FamilyLocationHeating

Olive Star Cottage & Garden (Pet Friendly)
FamilyLocationIndoor spaces

Olive Woods House - Catskills Mountain Views
LocationFamilyAccuracy

Modern Nature Escape w/Barrel Sauna & Yurt
LocationGetting aroundAmenities

Olive Outpost: Catskills 1BR Cabin on Private Road
ValueLocationWalkability

Epic Sunrise + Sunset, Treehouse Vibe, Wildlife
LocationFamilyDecor

High Point Meadows
FamilyLocationWalkability

Chef’s kitchen, firepit, 30 min to ski slopes
FamilyLocationComfort
When is the best time to visit Olive?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$61,002 GYD | G$61,002 GYD | G$59,958 GYD | G$62,673 GYD | G$66,852 GYD | G$68,105 GYD | G$70,821 GYD | G$69,567 GYD | G$61,211 GYD | G$68,941 GYD | G$65,389 GYD | G$69,150 GYD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Storm King Art Center
- Taconic State Park
- Plattekill Mountain
- Mohonk Preserve
- Bash Bish Falls State Park
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mohawk Mountain Ski Area
- Mount Peter Ski Area
- Storm King Art Center
- Millbrook Vineyards & Winery
- Hudson Chatham Winery





