Waterfront vacation rentals in Olive

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Olive

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

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Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 641 reviews

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.

Mar 31 – Apr 7

R2,470 ZAR per night

Guest favorite

Guesthouse in Accord

4.93 out of 5 average rating, 114 reviews

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.

Jul 25 – Aug 1

R1,894 ZAR per night

Guest favorite

Home in Stone Ridge

4.93 out of 5 average rating, 215 reviews

School house in the woods! Spring dates added.

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

Aug 21 – 28

R3,722 ZAR per night

Guest favorite

Home in West Shokan

4.86 out of 5 average rating, 119 reviews

Quiet, Peaceful & Secluded Streamside House,

Historic 3 Bedroom House near Woodstock, Phoenicia, Hunter and Belleayre Ski Centers. Available for seasonal, week & weekend rental with 2 Baths, Living Room, Dining Room, Eat in Kitchen, Woods, Stream, Fire Place, Burn Pit, 51" TV, 15' x 30' Deck, High Speed Internet, Great Cell Service, large yard, large hill, nicely secluded. We have Adirondack Reclining Chairs on 3 acres of property. The house is quiet & Peaceful next to Dry Brook surrounded by The Catskill Mountains.Certificate STR-23-24

Apr 17 – 24

R4,759 ZAR per night

Guest favorite

Cabin in Kingston

4.94 out of 5 average rating, 109 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!

Oct 8 – 15

R2,382 ZAR per night

Guest favorite

Cabin in Phoenicia

4.99 out of 5 average rating, 126 reviews

"A Stones Throw" Cabin on the Esopus Creek

The cabin is on a 1.2acre parcel nestled in an orchard between route 28 and the Esopus Creek, just West of Phoenicia. Activities for every season include biking, hiking, tubing, leaf peeping, skiing, snowshoeing, and antiquing. An outdoor fire pit and Adirondack chairs are provided creek side. When you finish enjoying the outdoors, you will find a charming cabin perfect for a relaxing get away. Check our other Airbnb cabin listing "Rocky Bottom" for additional family or friends accommodations.

Sep 30 – Oct 7

R3,050 ZAR per night

Guest favorite

Chalet in Napanoch

4.95 out of 5 average rating, 206 reviews

Catskills Aframe, Water View, Goat Sanctuary

This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house has a cozy feel with rustic charm and is the perfect getaway for those wishing to escape to nature. Outdoor enthusiasts will enjoy numerous local hiking trails and we're just 25 minutes from popular areas such as Mohonk Preserve, Sams Point, Minnewaska. A goat sanctuary, animal lovers can visit with our 29 recsue goats, chickens, dogs and of course, local wildlife!

Dec 9 – 16

R3,232 ZAR per night

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 428 reviews

*Great Reviews* Hunter Mtn. Close/Cozy/Clean Condo

*Clean, cozy studio condo in the Village of Hunter featuring vintage decor. Short walk to the Ski Slopes, Snowtubing Park, Scenic Skyride, Dolan's Lake/Beach, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. A Murphy bed w/ full size comfy Casper Mattress, a sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, strong WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

May 29 – Jun 5

R1,415 ZAR per night

Guest favorite

Home in West Shokan

4.87 out of 5 average rating, 116 reviews

Watson House 1850

1850 Watson House near the Catskill high peaks, with the beautiful sound of the nearby Bushkill Creek. Spacious, clean, peaceful. Fast reliable WIFI. Big stone fireplace. Two roomy bedrooms, screened porch, and a picket-fence. AC, fire pit with adirondack chairs. A comfortable mix of art and wooden mid-century minimalism. The house is in a beautiful natural area while a short drive to town, restaurants, farm stands. Favorite summer spot – the sunroom with french doors open to the garden!

May 17 – 24

R4,057 ZAR per night

Guest favorite

Cabin in Phoenicia

4.98 out of 5 average rating, 557 reviews

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

Jan 14 – 21

R3,818 ZAR per night

Guest favorite

Cabin in Kerhonkson

4.9 out of 5 average rating, 146 reviews

Adorable Cottage w/ Hot Tub, Pond, and Fireplace

Highlights: Cute-as-a-button secluded cottage with hot tub, pond, wood stove, and soaking tub. Very private, close to great hiking.. Welcome to Fern Pond, a modern but enchanting cottage in quiet Kerhonkson. In the shadow of the Sundown Wild Forest, this sweet house offers a cozy base to explore Accord, Stone Ridge and the Ashokan Reservoir. Enjoy its privacy, remoteness, and romanticism, while soaking in the hot tub and/or cozying up by the fire.

Dec 8 – 15

R5,121 ZAR per night

Guest favorite

Cabin in Boiceville

4.94 out of 5 average rating, 214 reviews

Catskills Mountain River Dream House

*Art-filled c. 1910 Cottage w/ wrap-around porch *A self-contained natural wonderland for grownups, kids, and dogs *Riverfront w/ private swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, surrounding woods *Badminton court *Mature perennial gardens *Fire pit *Hybrid Charcoal/Gas Grill *Hot outdoor shower overlooking Gardens *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll)

Nov 22 – 29

R5,291 ZAR per night