
Family-friendly holiday rentals in Olive
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Olive

Total holiday rentals
Explore 140 holiday rentals in Olive

Nightly prices starting at
Olive holiday rentals start at $119 NZD per night before taxes and fees

Verified guest reviews
Over 10,110 verified reviews to help you choose

Pet-friendly accommodation
Find 70 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
130 of Olive holiday 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 family-friendly rentals in Olive
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

The Lily Cottage Guesthouse
Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

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.

Catskills Mountain River Dream House
*Art-filled c. 1910 Cottage w/ wrap-around porch *Self-contained natural wonderland for grownups, kids, & dogs *Riverfront w/ amazing swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, classic tree swing, & surrounding woods *Speedminton court *Mature perennial butterfly gardens *Fire pit *Weber Gas Grill *Cedar hot outdoor rain shower nestled in side garden *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll); 2 adult bikes

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 😊

Stylish and Cozy Mountain Retreat
Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

Catskills Glamp Oasis w. Breakfast by the Pond
Namahai Retreat is about communing with nature, trees, the elements, pond, fire, birds, flowers, and frogs, and most importantly, yourself. Situated on a 5-acre homestead in the heart of the Catskills Mountains, privately tucked in a Pine Grove, we hope you enjoy the serenity, nature, and magic found here. Botanically, it is a feast for the eyes. Bird watcher's paradise. Night sky full of stars. Your stay includes one complimentary breakfast, bonfire, and firewood for the tent stove.

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.

The Ashokan Guest House
This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

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

PerchCottages #13: 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

Catskills Woodstock Design Retreat w/ hot tub
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

The Cottage
Located just a short drive north of NYC, nestled between Woodstock and Phonecia, is a little cottage waiting to be discovered by you or you and a guest! This is a stand-alone cottage apart from the main house on the property with its own designated parking, so you get this entire private oasis to yourself.
Popular amenities for Olive family-friendly rentals
Family-friendly home rentals with a hot tub

Willow Treehouse - secluded, unique, romantic

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Hot tub with stunning views, 5 min to Woodstock

Historic Catskills farmhouse with sweeping views

Architectural Private Gem w/ Views + Hot Tub

Mt. Wonder: Big Cozy Cabin with Wow View
Family- and pet-friendly home rentals

Dave's Milk Barn

Unique Barn Loft on Century Old Farm

Cozy Cabin | Fire pit + Hiking + Pets Welcome

Black A-Frame: Catskills Cabin

Lovely Cabin w/Piano No Car Needed Best Hiking

ENTER HOME - Minimalistic style warm & inviting

Cozy Catskill Cabin on Acorn Hill

Byrdcliffe Artist Studio (27.1-1-70)
Family-friendly home rentals with a pool

Shula | Farmhouse | Pool, Hot tub, Fire pit

midcentury mod * POOL * walk out trail R2R/Mohonk
Woodstock Historic Artist Estate - The Pond House

Scenic River View Escape | New Paltz

Secluded Woodstock Retreat -Heated Pool and Sauna

Woodstock Mountain Cottage w/ Swimming Pool

Cozy & Spacious Country Home - All Seasons

Peace & Privacy - High Falls (hot tub & salt pool)
When is the best time to visit Olive?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $479 NZD | $471 NZD | $447 NZD | $457 NZD | $491 NZD | $523 NZD | $520 NZD | $521 NZD | $479 NZD | $508 NZD | $494 NZD | $499 NZD |
| 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 |
Destinations to explore
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Plattekill Mountain
- Taconic State Park
- Mohonk Preserve
- Storm King Art Center
- Kent Falls State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Peekamoose Blue Hole
- Mount Peter Ski Area
- Harriman State Park
- Storm King Art Center
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Benmarl Winery





