Town of Olive, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Olive, New York on RentalSaver.com!

Town of Olive Rentals

From $320 per night (USD)
VRBO
Relaxing Catskill Mountain Cottage.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
1,000 sq ft. cottage, located on a seven acre, partially wooded property in the Catskills. Two bedrooms, one bathroom ...
From $320 per night (USD)
VRBO
From $551 per night (USD)
VRBO
Farm House
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a peaceful retreat in this historic farm house, outfitted with antique furniture and situated on 50 acres of beaut ...
From $551 per night (USD)
VRBO
From $739 per night (USD)
VRBO
Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing
Bedrooms:
3
Bathrooms:
4
Sleeps:
15
The cabin is cozy and rustic looking but with modern comforts. Featuring a large stone fireplace and expansive deck, gre ...
From $739 per night (USD)
VRBO
From $929 per night (USD)
VRBO
Modern Farmhouse Retreat with Heated Saltwater Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Modern 4 bedroom, 2.5 bath on 3.5 acres complete with swimming pool and fire pit. Enchanting colonial farmhouse has b ...
From $929 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Rustic Catskills Cabin, on 3 acres, between Woodstock & Phoenicia
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This Quintessential Catskills Cabin, built in the 1930s as a gentleman's hunting lodge, on 3 acres, is the perfect blen ...
From $317 per night (USD)
VRBO
From $902 per night (USD)
Expedia
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
We are pleased to announce this beautiful, rustic, four-bedroom, luxury mountain getaway home is NOW being offered at un ...
From $902 per night (USD)
Expedia
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VRBO
cottage over looking a lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In warm, fine weather, much time is wiled away on the porch, where a view over the lake provides a refreshing change of ...
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VRBO
From $253 per night (USD)
VRBO
Secluded Catskill Mountains Getaway Peaceful Nature Near Woodstook
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
WE ARE BACK!! Had to go through the Town of Olive for inspections and approval due to approval needed for any short-term ...
From $253 per night (USD)
VRBO
From $783 per night (USD)
VRBO
Secluded, Ski, Firepit, Pool, Getaway On 10 Acres
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
3 night minimum for main holidays. 1 week minimum for the Summer A spacious 3,100 sq ft ranch-style sanctuary sitting o ...
From $783 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Luxury Cottage for 2. Very close to Woodstock, NY.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a luxurious newly-renovated 1 BR, 1 bath, modern guest cottage privately sited away from the main house. It has ...
From $256 per night (USD)
VRBO
$Classic Cottage w/Beautiful Catskill View, on\n5 peaceful acres. Weekly discount!$
From $289 per night (USD)
VRBO
Classic Cottage w/Beautiful Catskill View, on\n5 peaceful acres. Weekly discount!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Cottage on the Hill is set on 5 acres of meadow and woodland, surrounded by a mountain view. The site is spectacular ...
From $289 per night (USD)
VRBO
From $474 per night (USD)
VRBO
Your Fun Catskills Getaway near Woodstock, Hunter and Belleayre.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Looking for a special place to relax? Bring your family and friends and make The Little Silver Guesthouse your special ...
From $474 per night (USD)
VRBO
From $604 per night (USD)
VRBO
High Point Mtn House ~ Celebrate Spring on the Mtn! Privacy! Gorgeous VIEWS!
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
High Point Mountain House is a special retreat with breathtaking views spanning from the Catskills to the Berkshires to ...
From $604 per night (USD)
VRBO
From $279 per night (USD)
VRBO
Woodland Cozy Cabin Catskills
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Winston's Place is a cozy cabin nestled into a wooded backdrop, in the Catskill Mountains. Quiet dead end road, large wr ...
From $279 per night (USD)
VRBO
From $478 per night (USD)
VRBO
Private 6 Acre Catskills Retreat Between Mohonk and Woodstock - Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Come enjoy our mountain retreat! This secluded 3000-square-foot craftsman home sits on 5.5 wooded acres set far off of ...
From $478 per night (USD)
VRBO
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Expedia
Perfect Catskills Getaway, 12 Minutes to Town of Woodstock.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming weekend getaway is 12 minutes from the center of Woodstock. On 8+ acres, furnished with comfortable elegan ...
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Expedia
From $650 per night (USD)
VRBO
Ravenscliff - Ulster County beauty in Catskill National Park STR Permit # =22-10
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
*First 2 children age 2 and under are free* "The human spirit needs places where nature has not been rearranged by the ...
From $650 per night (USD)
VRBO
From $266 per night (USD)
Expedia
Unplug. Reconnect. Take a midday nap in total silence. Retreat. Create. Say YES.
Bedrooms:
1
Bathrooms:
7
Sleeps:
12
The Short & Sweet description: Newly renovated book-filled home in the Town of Olive sleeps 12-15 across three floors (6 ...
From $266 per night (USD)
Expedia
From $1608 per night (USD)
VRBO
A Retreat @ Hudson Woods With Pool & Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
A Retreat @ Hudson Woods is a luxury oasis nestled in the private woods of Kerhonkson. Nearby breweries, farms, and fin ...
From $1608 per night (USD)
VRBO
From $456 per night (USD)
Expedia
A Retreat @ Hudson Woods: Pond House
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Retreat @ Hudson Woods is a luxury oasis nestled in the private woods of Kerhonkson. Nearby breweries, farms, and fin ...
From $456 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Upstate Kerhonkson Cottage on 2 acres w/ firepit and covered patio to guesthouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A little piece of heaven. Bright and airy little one-story cottage, 3 bedroom, 2 bath (in the warm months, 1 bath in the ...
From $590 per night (USD)
VRBO
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Expedia
Ultra modern getaway with pool and poolhouse in upstate New York
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
A beautiful modern home in the Catskills, exactly 2 hours away from New York City, with a heated saltwater swimming pool ...
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Expedia
From $283 per night (USD)
VRBO
Pet, Family, and Party Friendly house perfect for 3 or more couples
Bedrooms:
1
Bathrooms:
3
Sleeps:
11
My home is 10 minutes to Woodstock & Phoenicia. There are 2 ski resorts and dozens of hiking trails within 30 mins away ...
From $283 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Cozy Home with Hot Tub, Lots of peace /quiet with Mountain views Near Woodstock!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Olivebridge is a quiet and beautiful area! Close to the best hiiing trails in hudson valley! My home features a Jacuzzi ...
From $315 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or couple’s Catskill getaway! Situate ...
From $141 per night (USD)
VRBO
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Expedia
Catskills Cabin Near Ashokan Reservoir
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
- Remote-Work Friendly - Picturesque Forest Views - Hike, Bike, Ski + Fish Nearby Cozy up in the Catskills at this 2-be ...
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Expedia
From $474 per night (USD)
VRBO
Chic Country Home with Catskills Mountain Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Olive Woods House is located in the heart of the Catskills - a two bed, two bath, light and airy cottage cradled in ...
From $474 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Peaceful Retreat, Private Yoga Studio, Jacuzzi & Mountain Views | By Dream House
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Welcome to our luxurious and secluded Villa Retreat, a tranquil haven designed for both relaxation and adventure. Nestle ...
From $502 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Catskills Family Hideaway
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our beautiful home in Olivebridge combines the coziness of a cabin in the woods with the roominess and modern amenities ...
From $395 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Modern Farmhouse with Catskill Mountain Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This modern farmhouse located in the heart of the Catskills is a rare find and just 2 hours from NYC. Upon entering this ...
From $597 per night (USD)
VRBO
From $914 per night (USD)
VRBO
Historic Catskills farmhouse with sweeping views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Your getaway in the mountains awaits! Welcome to Juniper Grove - your country home in the Catskills. This 4 bedroom 2 fu ...
From $914 per night (USD)
VRBO
From $825 per night (USD)
Expedia
Modern Farmhouse • Sauna • Private Pond • Hiking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This newly constructed home is in the perfect location and setting to enjoy everything the Catskills Mountains has to of ...
From $825 per night (USD)
Expedia
From $290 per night (USD)
VRBO
A Romantic Escape, Woodstock Barn by A Stream with Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Large and cozy private barn, on five acres of wooded land, with a stream outside your window. Comfortable, with modern a ...
From $290 per night (USD)
VRBO
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Expedia
1789 Cabin on 27 Acres
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Minimum stay is 30 days. This cozy cabin is cool in the summer and toasty in the winter. Its both remote and close to ...
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Expedia
From $308 per night (USD)
VRBO
Ashokan ArtHaus, Private Hot Tub, Wags Welcome!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Ashokan ArtHaus, our stylish, architect-designed home designed for 4 guests. Nestled across from the Ashokan ...
From $308 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Cozy Catskills Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Be it high summer or snowy winter, this is the place to chill! A long shady driveway brings you to the Cottage, a two be ...
From $199 per night (USD)
VRBO
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VRBO
Renting full month of August -quiet, private fenced house w/ pool near NYC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your exclusive paradise in Stone Ridge, nestled in the picturesque Catskills, just a short 2hr drive from NYC ...
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VRBO
From $255 per night (USD)
VRBO
Peaceful, Secluded Olivebridge Cottage. Huge Garden with Fire Pit. Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Wake up in this private tranquil retreat. The cozy, 2 bed 1 bath mid-century modern cottage is located on over two acres ...
From $255 per night (USD)
VRBO
From $608 per night (USD)
VRBO
NEW LISTING! Modern Luxury Catskills Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape the hustle and bustle of the city and immerse yourself in the breathtaking beauty of the Catskill Mountain Region ...
From $608 per night (USD)
VRBO
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Expedia
Catskills Farmhouse and Summertime Fun!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This picturesque 1850's farmhouse w modern amenities (fr. WiFi to full Kitchen) is all Mountain behind the house! Locate ...
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Expedia
From $196 per night (USD)
VRBO
West Wing - a unique private space w/patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
About this space This unique studio space with private entrance is a recent addition to our charming home, located on a ...
From $196 per night (USD)
VRBO
From $700 per night (USD)
VRBO
NEW LISTING Woodstock secluded mountain retreat with beautiful pool and sauna.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and ...
From $700 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Close to Hiking Trails-Skiing! Located In a quiet Home with Mountain View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Home Is such a peaceful Escape! It brings such a calm feeling watching the sun come up and listening to the birds! ...
From $252 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Stunning Modern House/Cottage minutes from Woodstock NY.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape year-round to this stunning, renovated property in the picturesque Catskills, perfect for groups or large family ...
From $519 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Catskills Mountain Ski Retreat with amazing views
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Views, Privacy and Style! Travel a paved drive to this 2400+ sf contemporary retreat with stunning views of the majestic ...
From $427 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Catskills Retreat on 10 Acres w/ Private Creek
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Our quiet little slice of the Catskills is the perfect retreat! Located on 10+ wooded acres with private creek access. 3 ...
From $412 per night (USD)
Expedia
$\nModern Farmhouse in the Catskills on 5 acres of land. Ski resorts close by!$
From $192 per night (USD)
VRBO
\nModern Farmhouse in the Catskills on 5 acres of land. Ski resorts close by!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 bedroom, 2 bathroom newly renovated house sitting on 5 acres of land is available for your getaway. This special house ...
From $192 per night (USD)
VRBO
From $474 per night (USD)
VRBO
Abbey Rd Farmhouse: Pool, Firepit + Stunning Views
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Summary: Nestled in the heart of tranquil upstate New York, Abbey Road Farmhouse offers an idyllic escape just 2.5 hours ...
From $474 per night (USD)
VRBO
From $673 per night (USD)
VRBO
Atomic Ranch - MCM One Level in Olivebridge. Great Outdoor Space!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Highlights: Updated ranch in the perfectly placed hamlet of Olivebridge. Great open living and dining room, fireplace, ...
From $673 per night (USD)
VRBO
From $559 per night (USD)
Expedia
Rose Meadow: Quiet 1800s Farm House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
A quiet and beautiful 19th century farm house nestled in the foothills of the Catskills, Rose Meadow includes stunning m ...
From $559 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Bluestone Cove - Modern Escape in the Woods
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Discover the magic of Bluestone Cove, a secluded 3-bed, 2-bath modern retreat in NY's serene Olivebridge - jus ...
From $581 per night (USD)
VRBO
From $265 per night (USD)
VRBO
Visit a farm-stay container house on a 30-acre organic forest in Stone Ridge, NY
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Reconnect with nature at this unforgettable escape. A tiny house container building designed and built by your host set ...
From $265 per night (USD)
VRBO
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VRBO
Quiet Luxury Retreat in the Catskills -- 2 bedrooms, Designer Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tucked into one of the coziest corners of the Catskills, this is the perfect place to unwind from the demands of urban l ...
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VRBO
From $977 per night (USD)
Expedia
Hudson Valley Black Barn: Views-Fireplace-Pit-Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Escape to Black Barn Ranch, a sleek & warm Scandinavian retreat in the Catskills, just 2.5 hours from NYC. This ...
From $977 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Charming Catskills Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the charm of our unique and intimate studio home, ideal for a delightful and snug retreat. Situated on a tran ...
From $167 per night (USD)
VRBO
From $258 per night (USD)
Expedia
3BR Quiet Retreat in Catskills | Fire pit | Pets
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Gather your loved ones and embark on an unforgettable getaway to our recently listed modern retreat in the captivating C ...
From $258 per night (USD)
Expedia
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VRBO
Pool, Hot Tub, Fire Pit, Gym - Upstate Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to your Upstate Escape, a luxurious retreat in the peaceful Hudson Valley. With a pool, hot tub, fire pit, and h ...
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VRBO
From $413 per night (USD)
Expedia
Charming 2-bedroom cottage on private 4 acres with modern amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your home away from home in Olivebridge, this charming cottage provides historic features, stunning views and serene pri ...
From $413 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Catskills Mountain Riverfront Dream House
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
*Art-filled c. 1910 Cottage w/ enchanting wrap-around porch *2-bedrooms, full bath, well-stocked cook's kitchen with f ...
From $376 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Catskills Creekside Sanctuary
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy our peaceful, updated Shokan home in the Catskills. This delightful house features 1 king bed and 2 queen beds, 3 ...
From $447 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Cozy Log Cabin with Hot Tub, Firepit & Prime Catskills Location
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Tucked away in the woods but close to everything, this classic log cabin retreat is your perfect upstate escape—just min ...
From $491 per night (USD)
VRBO
From $680 per night (USD)
VRBO
Catskills Mountain House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Brand new designer home, with stunning architectural features , nestled in the Catskill mountains, close to Woodstock, ...
From $680 per night (USD)
VRBO
From $2578 per night (USD)
VRBO
A Retreat @ Hudson Woods With Main & Guest House
Bedrooms:
5
Bathrooms:
6
Sleeps:
18
A Retreat @ Hudson Woods is a luxury oasis nestled in the private woods of Kerhonkson. Nearby breweries, farms, and fine ...
From $2578 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Wooded Way: Forest Views | Starry Skies | Scenic Days
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Wooded Way is a charming 3 bed, 1.5 bath contemporary getaway just under 2 hours from NYC close to the Ashokan ...
From $384 per night (USD)
VRBO

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Town of Olive Rentals

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Results: 64 Rentals