Waterfront vacation rentals in Olive

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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

4.94 out of 5 average rating, 347 reviews

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.

Guest favorite

Guesthouse in Accord

4.94 out of 5 average rating, 156 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.

Top guest favorite

Cabin in Boiceville

4.95 out of 5 average rating, 253 reviews

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

Guest favorite

Home in Stone Ridge

4.9 out of 5 average rating, 257 reviews

*summer and fall dates* 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

Top guest favorite

Cabin in Margaretville

4.99 out of 5 average rating, 186 reviews

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.

Guest favorite

Cabin in Kingston

4.93 out of 5 average rating, 235 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!

Guest favorite

Cabin in Wurtsboro

4.97 out of 5 average rating, 346 reviews

Summer Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Guest favorite

Home in West Shokan

4.87 out of 5 average rating, 127 reviews

Stream-side Home, Quiet, Peaceful & Secluded

Stream side, Historic 3 Bedroom Home 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, 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 home is quiet & Peaceful next to Dry Brook surrounded by The Catskill Mountains. Cert. STR-23-24

Guest favorite

Home in Mount Tremper

4.93 out of 5 average rating, 232 reviews

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View

Welcome to the most splendid view in the Catskills. With a private outdoor spa. And just 10 min to Woodstock. This secluded cabin sits on 18 acres w/ private creek access & forest. Seeking a vacation w friends or a romantic escape? This is the place. Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub, sauna & cold plunge Amenities galore incl the spa, BBQ, firepit, games, wood stove & stocked kitchen. Peruse our books, be in nature or enjoy hikes & towns. This is the one.

Guest favorite

Cabin in Phoenicia

4.97 out of 5 average rating, 635 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

Top guest favorite

Cabin in Chichester

4.99 out of 5 average rating, 260 reviews

Catskill Mtn Streamside Getaway

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.”

Superhost

Cabin in Kerhonkson

4.87 out of 5 average rating, 208 reviews

Cute Cottage w/ Hot Tub, Pond, and Rain Deck

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.