
House holiday rentals in Olive
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Top-rated house rentals in Olive
Guests agree: these houses are highly rated for location, cleanliness and more.

Dutch Touch Woodstock Cottage
The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

*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

Forest Retreat in the Gunks | Cozy Mountain Escape
Set on the side of the Gunks and surrounded by quiet forest, this warm, cozy home is designed for guests who love nature and simple comfort. Just minutes from Minnewaska and Stony Kill Falls. Enjoy wood-burning stove, a handmade L-couch, premium queen mattresses, a forest-view kitchen stocked with high quality coffee, tea, and essentials. Thoughtful touches include incense, essential oils, Puracy toiletries, and a meaningful library. Two porches facing the woods create a warm, peaceful escape.

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.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE 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 a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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.

Little Minka - Japanese House in the Woods
Little Minka. A serene Japanese folk house nestled on 10 acres of private woodland and streams. Embracing the Wabi-Sabi, Little Minka is unique, handcrafted using Japanese traditional carpentry joinery methods. Soaring ceilings, shoji, and tatami complete the interior. Outside there's a fire pit, open cooking area. We have a wood fired hot tub available on request from March - November. We have Japanese bathroom products in partnership with sowakanyc that guests can experience.

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.

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!

Cook House | Modern Cottage w/ Hot Tub & Fireplace
Featured in Vogue, Curbed, and Remodelista, Cook House by Reset Club is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature.
Fenced & Salt Water Pool | Cozy Catskills Cottage
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.

Overlook Creek Cottage 1 Near Phoenicia
Located on the Esopus, Overlook Creek Cottage is a newly renovated space including modern kitchen and bathroom amenities, mid century modern design with a Bohemian flair and proximity to destinations such as the town of Phoenicia, The Pines restaurant, Phoenicia Diner, Foxfire Mountain House, The Emerson Resort and Mt. Tremper Arts. Nearby to hiking trails and other towns such as Woodstock and Kingston as well as the Ashokan Reservoir.
Popular amenities for house rentals in Olive
House rentals with a pool

midcentury mod * HOT TUB * walk out trail 2 mohonk

Scenic River View Escape | New Paltz

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

4Br Mountain Brook House on 130 acres w/ trails

Highwoods Haven | saltwater pool and hot tub

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Upstate Modern Scandinavian Barn in the Catskills
Weekly house rentals

Stunning Modern Barn minutes from Woodstock 21N195

Mahali Petu - A Big Little House

Retro-Chic Cabin in Woodstock - Sauna

Architect's Farmhouse in Woodstock

Cozy cottage with firepit and walking trails

Stylish Country Escape near Kingston and New Paltz

Beautiful farmhouse with Mountain View- HITS- AC

DeMew House in Historic Kingston
Private house rentals

A Cozy’s Woodstock Getaway Home

Upstate Waterfront Saugerties Retreat-Near HITS

Olive Outpost: Catskills 1BR Meadow House For 2

Creekside Cottage

10 Min from Bellayre! Gingerbread House!

Eclectic one-bedroom house

The Stone House

Modern Mountain Retreat with Views on 18 Acres
When is the best time to visit Olive?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $351 SGD | $346 SGD | $287 SGD | $340 SGD | $356 SGD | $383 SGD | $433 SGD | $425 SGD | $374 SGD | $421 SGD | $400 SGD | $423 SGD |
| 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 |
Quick stats about house rentals in Olive

Total holiday rentals
Explore 100 holiday rentals in Olive

Nightly prices starting at
Olive holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 6,250 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
100 of Olive holiday rentals include wifi 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!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Resorts World Catskills
- Windham Mountain
- Mount Peter Ski Area
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
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- Opus 40
- Warwick Valley Winery & Distillery
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- Poets' Walk Park
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- Millbrook Vineyards & Winery




