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Waterfront vacation rentals in Olive

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Quick stats about waterfront rentals in Olive

  • Total vacation rentals

    Explore 20 vacation rentals in Olive

  • Nightly prices starting at

    Olive vacation rentals start at €104 per night before taxes and fees

  • Verified guest reviews

    Over 2,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 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 waterfront rentals in Olive

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Boiceville

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

4.95 out of 5 average rating, 281 reviews
Top guest favorite
A cozy seating area features a light-colored sofa and a red sofa, both positioned around a wooden coffee table. A modern area rug is laid beneath them, while strategically placed lights illuminate the space from above.
Guesthouse in Accord

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.

4.94 out of 5 average rating, 187 reviews
Guest favorite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

4.94 out of 5 average rating, 398 reviews
Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

4.88 out of 5 average rating, 220 reviews
Top guest favorite
Home in High Falls

Comfortable & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods, pond and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

4.98 out of 5 average rating, 121 reviews
Guest favorite
Cabin in Phoenicia

Mountains and Rivers, Secluded Cabin

"Of all the retreats I have found among the Catskills there is no other that possesses quite so many charms for me as this valley. It is so wild, so quiet and has such superb views." - John Burroughs. Our beautiful cabin, tucked into a secluded hollow at the base of Romer Mountain, sits by Woodland Valley Creek. A couple of miles up the road are trailheads to Giant Ledge, Panther, Wittenberg and Slide. Phoenicia hamlet is 4 miles away. Woodstock, Belleayre and Hunter are within 1/2 hour.

4.93 out of 5 average rating, 120 reviews
Guest favorite
A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.
Home in Mount Tremper

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"

4.93 out of 5 average rating, 276 reviews
Top guest favorite
An inviting tent interior features a large, cozy bed adorned with textured bedding. A central wooden table holds decorative items and a lantern, while plush floor cushions are positioned nearby. The space is enhanced by light filtering through the tent fabric, casting playful shadows.
Tent in Kerhonkson

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.

4.99 out of 5 average rating, 105 reviews
Guest favorite
A wooden dining table is set in the kitchen, featuring a welcome sign beside a purple water bottle and a decorative vase filled with fresh flowers. A bag of popcorn sits at the edge of the table, and kitchen appliances are visible in the background.
Home in Stone Ridge

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

4.9 out of 5 average rating, 302 reviews
Top guest favorite
A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.
Home in Kingston

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!

4.95 out of 5 average rating, 370 reviews
Top guest favorite
The Treehouse is nestled among trees, elevated above a tranquil pond. Its wooden structure features large windows that provide views into the surrounding greenery, while the natural landscape is reflected in the pond's surface. The setting offers a secluded feel contrasting with the nearby wooded area.
Treehouse in Willow

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

4.96 out of 5 average rating, 873 reviews
Guest favorite
A quaint cottage is surrounded by lush greenery, featuring a striking red front door. Sunflowers rise in the foreground, adding a touch of color. The wooden deck extends towards the peaceful landscape, showcasing the cottage's inviting exterior.
Guesthouse in Mount Tremper

Cozy Catskill Cottage Perfect Getaway for Two

COZY, QUIET, CLEAN, AND SECURE Cottage in a 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. 20 minutes to Woodstock and its numerous sophisticated dining and shopping options. 20 minutes to Belleayre and Hunter for 4-season happenings. Perfect for couples who need a weekend country getaway.

4.92 out of 5 average rating, 391 reviews

Popular amenities for Olive waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favorite
A modern studio features a spacious bed draped in white bedding with blue accents, alongside a cozy seating area with a dark sofa. Floor-to-ceiling glass windows provide stunning views of the river and open onto a private terrace, enhancing the serene ambiance.
Apartment in Ulster Park

Escape to a Sleek, Serene Studio on the Riverbank

4.99 out of 5 average rating, 461 reviews
Top guest favorite
A spacious living area features a futon decorated with patterned cushions and a striking red pool table. A light fixture with multiple bulbs hangs overhead, while a wall-mounted TV is visible in the background. Large pocket doors separate the living space from the bedroom.
Apartment in Kingston

Lovely 1 bedroom apt. with free parking in Rondout

4.98 out of 5 average rating, 233 reviews
Guest favorite
The entrance features a striking red door adorned with a brass plaque labeled 'DeMew Townhouse.' Lush green vines and colorful flower pots with blooming flowers are positioned at the foot of the stairs, enhancing the welcoming atmosphere of the entryway.
Apartment in Kingston

DeMew Townhouse in Historic Kingston

4.95 out of 5 average rating, 317 reviews
Top guest favorite
A tall, rusted trestle bridge spans the landscape, surrounded by lush green trees that showcase varying shades of yellow and green. The structure rises above the foreground, with a glimpse of a house nestled among the trees below.
Apartment in Rosendale

Rosendale Trestle View

4.96 out of 5 average rating, 232 reviews
Guest favorite
Apartment in Newburgh

Special Nest w Private Entrance River View Porches

4.89 out of 5 average rating, 274 reviews
Guest favorite
The living area features a spacious sofa, accented with patterned throw pillows, placed in front of a wooden coffee table. Sunlight enters through multiple windows, illuminating the room's warm wood floors and green walls. A dining area with natural wood chairs is visible in the background.
Apartment in Round Top

🏔O'Clarke Mountain House - The Catskills

4.96 out of 5 average rating, 130 reviews
Top guest favorite
A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.
Apartment in Coxsackie

Hudson River Beach House

4.99 out of 5 average rating, 166 reviews
Guest favorite
A spacious kitchen and dining area feature light wood cabinetry and modern stainless steel appliances. A wooden dining table is complemented by white chairs, and a window seat provides natural light. Decorative elements include a bowl of fruit at the center of the table.
Apartment in Beacon

Top Floor 2BR

4.85 out of 5 average rating, 781 reviews

Waterfront house rentals

Top guest favorite
A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.
Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

4.98 out of 5 average rating, 130 reviews
Top guest favorite
A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.
Home in Saugerties

The Stone House

4.98 out of 5 average rating, 195 reviews
Guest favorite
An outdoor area is visible through a large window, featuring a vintage clawfoot bathtub and a wooden stool. A hammock is suspended nearby. Lush greenery surrounds the space, creating a serene atmosphere.
Home in Spring Glen

Creekside cottage on 65 acres

4.94 out of 5 average rating, 247 reviews
Guest favorite
The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.
Home in New Paltz

Welcome to The Boathouse! Waterfront/Boats/Hot tub

4.92 out of 5 average rating, 395 reviews
Top guest favorite
A peaceful outdoor space is presented, featuring a fire pit surrounded by seating chairs on a grassy area. A hammock is seen in the background, providing a cozy spot for relaxation amid lush greenery. The natural setting invites calmness and outdoor enjoyment.
Home in Woodstock

Brookside, Walk to Town Center, Dog Friendly

4.91 out of 5 average rating, 534 reviews
Guest favorite
A fire pit is surrounded by four wooden Adirondack chairs on a gravel circle, positioned near a serene waterfront. Lush green trees frame the scene, providing a natural backdrop to this inviting outdoor gathering space.
Home in Lake Katrine

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

4.95 out of 5 average rating, 106 reviews
Top guest favorite
The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.
Home in Woodstock

Dutch Touch Woodstock Cottage

4.91 out of 5 average rating, 783 reviews
Top guest favorite
Two Adirondack chairs are positioned near a tranquil lake, offering views of the surrounding green trees and hills. A fire pit is located in front of the chairs, with large rocks scattered around the area, enhancing the natural setting.
Home in Chichester

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit

4.97 out of 5 average rating, 187 reviews

Waterfront condo rentals

Guest favorite
A studio condo features a cozy sleeping area with a patchwork quilt covering a spacious bed. A TV is positioned on a wooden dresser, while a red sectional couch is adorned with various patterned pillows. Ambient light enters through a window, creating a welcoming atmosphere.
Condo in Hunter

Hunter Mtn. Clean Cozy Close Condo *Great Reviews*

4.95 out of 5 average rating, 564 reviews
Guest favorite
A clear swimming pool is enclosed by a fence, featuring a ladder for easy access. Lush greenery and the mountains are visible in the background, with lounge chairs positioned nearby. The scene is set under a bright blue sky with wispy clouds.
Condo in East Jewett

StunningViews•Bright2BR•Pool•NearFarm•Lakes•Farm

4.94 out of 5 average rating, 157 reviewsA bright dining area features a large wooden table surrounded by six chairs. Light-colored cabinets and countertops create an inviting kitchen space. Various kitchen appliances and decorative items are displayed on shelves, contributing to the functional and spacious environment.
Condo in Hunter

Snowboarding skiing Mountain View condo

4.77 out of 5 average rating, 327 reviews
Top guest favorite
A spacious living area showcases a large sectional sofa adorned with decorative pillows. A wooden coffee table is centrally positioned on a patterned area rug. The open kitchen features a breakfast bar with seating, and appliances are visible along the wooden cabinetry.
Condo in Hunter

Trailside Tranquility at Hunter Mountain

5.0 out of 5 average rating, 36 reviews

When is the best time to visit Olive?

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Avg. price€162€196€156€171€179€172€175€190€155€160€141€137
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