
Waterfront holiday rentals in Olive
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Top-rated waterfront accommodation in Olive
Guests agree: These waterfront accommodation options 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.

Phoenicia Wild Garden Guesthouse--near everything!
Charming light-filled guesthouse at edge of a wild forest--but close to town! Walk to prime hiking and fishing. 2 min. to town restaurants, shops, other fun activities. NYC bus is walking distance. 20 minutes to major ski areas and Woodstock! All new custom full bath. Cozy king size loft bed sleeps 2 adults. Full size bed on main level, with memory foam comfort! Wi-Fi, Wi-Fi calling, Verizon cell service; landline phone. Fire pit, propane grill, well water. Gorgeous garden, brook, must see!

Studio in Private Forest; Peace and Solitude
Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

Brookie • Creekside • Fires • BBQ • Fishing
**Self-check in and fully sanitized by CDC guidelines** This stream side cabin is located in the heart of the Catskill Mountains. It is the perfect get-a-way for people looking to be outside by nature while having a beautiful living and working space. Located steps away from the Esopus Creek, peaceful sounds of rushing water can be heard in and out of the cabin. The cabin has a deck that overlooks the river, outdoor fire-pit w/ Adirondack chairs, a grill, picnic table & an indoor gas fireplace.

*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

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.

DeMew House in Historic Kingston
PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Cozy Catskills Cottage on the Esopus Creek
Our beautiful cottage has cozy charm and modern amenities. Located on the Esopus Creek, near the town of Phoenicia. Enjoy the restaurants and shops nearby, or cuddle up near a warm fire after hitting the slopes. Relax to the sound of the river after a day of hiking or tubing. One queen bed and one lush futon make this a couples or family get away. Surround yourself with the peace and quiet of nature any time of year. The Catskills are calling.. License # 2022-STR-015

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

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!

Willow Treehouse - secluded, unique, romantic
The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Cozy Catskill Cottage Perfect Getaway for Two
NEWLY RENOVATED, COZY, CLEAN, PRIVATE AND SECURE Cottage in scenic and peaceful locale. Convenient and easy to find near the town of Phonecia, NY. 100 PACES to the ESOPUS RIVER and its trout fishing, trail heads and scenic hikes less than a mile away. Close to numerous sophisticated dining and shopping options. Less than 30 minutes to BelleAyre and Hunter Summer Happenings. Perfect for couples who need a weekend country getaway.
Popular amenities for Olive waterfront rentals
Waterfront apartment accommodation

Lovely 1 bedroom apt. with free parking in Rondout

Hudson River Beach House

Waterfront Escape 1BR w/Private Balcony & Bikes

STREAMSIDE CATSKILL MOUNTAIN HOUSE

Escape to a Sleek, Serene Studio on the Riverbank

Scenic Hudson River Getaway!

Special Nest w Private Entrance River View Porches

Esopus Bend Getaway - 4 min to HITS
Waterfront house rentals

Waterfront Three bedroom in Saugerties w/ Hot Tub

Upstate Waterfront Saugerties Retreat-Near HITS

Modern Catskills Tiny House Near Hiking Trails

Creekside Cottage
Woodstock Historic Artist Estate - The Pond House

Scenic River View Escape | New Paltz

Victorian Haven

Welcome to The Boathouse! Waterfront/Boats/Hot tub
Waterfront condo accommodation

Snowboarding skiing Mountain View condo

Perfect Catskills hiking getaway with fireplace

Hunter Mtn. Cozy Close Clean Condo *Great Reviews*

1/2 Mi to Windham Mtn: Main Street Condo

Hunter creekside condo with mtn. view

SereneCatskillsMoutainsGetawayMinutesToSkiResorts
When is the best time to visit Olive?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $264 NZD | $266 NZD | $240 NZD | $243 NZD | $273 NZD | $287 NZD | $335 NZD | $363 NZD | $297 NZD | $307 NZD | $271 NZD | $263 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 |
Quick stats about waterfront rentals in Olive

Total holiday rentals
Explore 20 holiday rentals in Olive

Nightly prices starting at
Olive holiday rentals start at $198 NZD per night before taxes and fees

Verified guest reviews
Over 2,760 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Olive holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Waterfront rentals Ulster County
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- Waterfront rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Windham Mountain
- Mount Peter Ski Area
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Plattekill Mountain
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Mohawk Mountain Ski Area
- Bear Mountain State Park
- Taconic State Park
- Opus 40
- Benmarl Winery
- Warwick Valley Winery & Distillery
- Millbrook Vineyards & Winery
- Mohonk Preserve
- Upper Delaware Scenic and Recreational River




