Waterfront holiday 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 favourite

Home in Woodstock

4.94 out of 5 average rating, 338 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 favourite

Guest house in Accord

4.93 out of 5 average rating, 147 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 favourite

Cabin in Boiceville

4.95 out of 5 average rating, 244 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

Superhost

Home in Stone Ridge

4.9 out of 5 average rating, 253 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

Guest favourite

Yurt in Shandaken

4.96 out of 5 average rating, 261 reviews

Phoenicia Cozy Yurt - Spring! Sweet Spring!

5 minutes from Phoenicia. A comfy Yurt for 2 amid wild elderberries, peach trees, a goldfish pond and forested hills. A private back meadow for sun worshiping and meditation. Cold, UV purified mountain spring water. Skiers welcome: Cozy heat in the Yurt down to 10 below! The gas fired hot shower is glass enclosed and solar warmed on sunny mornings. 12v & 110v electric & fast WiFi. Odor-free, cedar, maple, and mahogany composting toilet. Mini-kitchen with tasty treats. Fire circle and gas grill.

Guest favourite

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 favourite

Home in Mount Tremper

4.93 out of 5 average rating, 225 reviews

Mt. Wonder - Hot tub, sauna, wonderful 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.

Superhost

Flat in Newburgh

4.86 out of 5 average rating, 190 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guest favourite

Cabin in Phoenicia

4.97 out of 5 average rating, 623 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

Superhost

Cabin in Kerhonkson

4.87 out of 5 average rating, 203 reviews

Cozy 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.

Guest favourite

Treehouse in Willow

4.96 out of 5 average rating, 797 reviews

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

Guest favourite

Guest house in Mount Tremper

4.92 out of 5 average rating, 355 reviews

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.