Waterfront holiday rentals in Olive

4.95 out of 5 average rating, 279 reviews

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

RiverViewSleep quality

4.93 out of 5 average rating, 269 reviews

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 secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Ten min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2br 1ba cabin, cozy and spacious, with a unique magical feel. Mega amenities incl the tub, BBQ, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin cabin: "Wonders Never Cease"

ViewRiverAccess

4.9 out of 5 average rating, 299 reviews

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

*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

ViewNearbyLocation

4.93 out of 5 average rating, 183 reviews

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.

ViewRiverIndoor spaces

Superhost

An exterior view of a tiny cabin nestled among tall trees, featuring a wooden deck and a distinct rustic façade. The pitched metal roof reflects light, while the welcoming entrance is framed by the surrounding nature.

Cabin in Kingston

4.92 out of 5 average rating, 311 reviews

Cabin 192

No cleaning fee and no 2-night minimum! Cabin 192 is a tiny home glamping experience located in lovely Kingston, NY. Cabin 192 takes you back to 1992 with: a vhs collection of classics, a Super Nintendo, Sega, and other fun activities. Warm and toasty in fall and winter and cool in summer you’re always comfortable at Cabin 192. Enjoy smores by the fire surrounded by trees in nature while also being able to enjoy a vibrant uptown district a 9-minute drive away! Minnewaska and Woodstock nearby!

ViewBathroomKitchen

4.99 out of 5 average rating, 303 reviews

Cabin in Chichester

Catskill Mtn Streamside Getaway - With EV Charger

Escape to this intimate one-bedroom Catskill cabin, nestled in a private yard with a trout stream at your doorstep. Just minutes from the charming town of Phoenicia, this retreat offers incredible hiking trails, three nearby ski resorts, and direct trout fishing access. Relax on the back porch with breathtaking views of snow-capped mountains or cozy up by the fireplace after a day of exploring. Perfect for couples or solo adventurers seeking peace and serenity.” EV Charger on site upon request.

BeachRiverKitchen

5.0 out of 5 average rating, 269 reviews

The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.

Cabin in Margaretville

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

ViewRiverAmenities

4.98 out of 5 average rating, 173 reviews

A serene view of the cabin set amidst lush greenery, with a calm stream flowing nearby. The deck is visible, and seating areas are arranged on the manicured lawn. Surrounding trees offer a sense of seclusion, enhancing the natural ambiance of the location.

Cabin in Hardenburgh

Catskills Cabin Oasis: Hot Tub, Hike, Creek, Relax

Escape to a secluded Catskills cabin with hot tub, forest views, fireplace, and walkable access to Balsam Lake Trailhead. Relax in the hot tub under the stars, enjoy coffee on the deck beside a babbling creek, and unwind by the historic fireplace built in 1920. Just 10 minutes to Belleayre Mountain for skiing, tubing, hiking, and lake days. Perfect for couples getaways, family weekend escapes, hiking trips, ski weekends, and year-round Catskills adventures. Welcome to Catskill Cabin Oasis!

ViewRiverAir conditioning

4.99 out of 5 average rating, 101 reviews

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.

Wi-FiIndoor spacesComfort

4.96 out of 5 average rating, 261 reviews

A cozy cottage is set within a wooded landscape, featuring a combination of black exterior and a warm wooden porch. Four Adirondack chairs surround a fire pit, with colorful plant arrangements enhancing the natural setting among fallen leaves.

Cottage in Bearsville

Mirror Moon Cottage (waterfront)

Mirror Moon cottage is a newly renovated, original 1960's cottage in the heart of a historic arts and music community. The property is waterfront, overlooking the Saw Kill, with tranquil views & sounds. Imagine falling asleep to the sounds of the river on our hammock. Only an 8 min bike ride, or 4 min drive to the center of Woodstock town. It's subtly tucked into the woods, just outside of town. Perfect for a friends or couples getaway! Make yourself at home!

ViewRiverWalkability

4.95 out of 5 average rating, 366 reviews

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!

RiverBeachAir conditioning

4.96 out of 5 average rating, 869 reviews

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

ViewOutdoor spacesWi-Fi

Popular amenities for Olive waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.99 out of 5 average rating, 458 reviews

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

ViewRiverParking

4.95 out of 5 average rating, 310 reviews

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

ViewRiverParking

4.96 out of 5 average rating, 229 reviews

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

ViewRiverOutdoor spaces

Apartment in Margaretville

A serene view is presented from a window, showcasing the calm water of a river bordered by grassy banks. In the background, gentle hills are visible under a clear blue sky. Nearby buildings feature charming architectural details, enhancing the quaint village setting.

4.96 out of 5 average rating, 201 reviews

Binnekill Views Apt.1 in the Catskill Mountains

RiverViewBathroom

4.98 out of 5 average rating, 227 reviews

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

ConditionLong stayGetting around

4.86 out of 5 average rating, 117 reviews

Apartment in Millbrook

The Bennett Cabin

ViewRiverAir conditioning

4.89 out of 5 average rating, 270 reviews

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

ViewRiverLayout

4.87 out of 5 average rating, 161 reviews

A marina scene is depicted with several boats docked along the water. The reflections of the boats and surrounding greenery are visible on the calm surface of the water. Trees provide shade, and buildings in the background include a blue-roofed structure.

Apartment in Saugerties

Saugerties Marina Peaceful Setting On the Water

ViewRiverHospitality

Waterfront house rentals

4.99 out of 5 average rating, 143 reviews

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

ViewRiverBathroom

4.94 out of 5 average rating, 393 reviews

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

BeachRiverParking

5.0 out of 5 average rating, 112 reviews

A spacious stone house is set against a clear blue sky, surrounded by lush greenery. A covered porch with large windows offers a seating area with decorative chairs. The well-maintained lawn enhances the inviting appearance of the property.

Home in New Paltz

The River House

RiverViewTV

4.88 out of 5 average rating, 233 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

ViewRiverComfort

4.94 out of 5 average rating, 246 reviews

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 of land

ViewRiverTV

4.96 out of 5 average rating, 428 reviews

A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.

Home in Livingston Manor

Peaceful creekside retreat near Livingston Manor

ViewRiverBreakfast

4.92 out of 5 average rating, 390 reviews

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

RiverViewPets

4.91 out of 5 average rating, 777 reviews

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

RiverViewTV

Waterfront condo accommodation

4.94 out of 5 average rating, 155 reviews

A spacious living area features large windows offering mountain views. A beige couch with textured cushions sits on a plush carpet. A wooden coffee table is positioned in front of the couch, complemented by a decorative wall hanging. A guitar rests on the floor beside a low bench.

Condo in East Jewett

Stunning Views • Bright 2BR • Pool • Near Farm • Lakes • Farm

ViewBackyardQuiet

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.

4.94 out of 5 average rating, 561 reviews

Hunter Mtn. Clean Cozy Close Condo *Great Reviews*

RiverBeachTV

5.0 out of 5 average rating, 26 reviews

Hunter creekside condo with mtn. view

ViewHeatingHiking

A 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.

4.77 out of 5 average rating, 327 reviews

Snowboarding skiing Mountain View condo

ViewRiverComfort

A modern kitchen is showcased with wooden cabinetry, granite countertops, and stainless steel appliances. An open design includes a breakfast bar with two stools and a glimpse of the red front door. Natural light is introduced through the windows, enhancing the space.

Condo in Windham

4.76 out of 5 average rating, 37 reviews

1/2 Mi to Windham Mtn: Main Street Condo

HospitalityNearbyTV

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.