Town of Olive Rentals
From $396 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 $396 per night (USD)VRBO
From $395 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 $395 per night (USD)VRBO
From $632 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 gem away ...
From $632 per night (USD)VRBO
From $702 per night (USD)Expedia
High Point Mtn House ~ Celebrate Summer ~ Privacy ~ SERENITY NOW~ 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 $702 per night (USD)Expedia
From $364 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 $364 per night (USD)VRBO
From $870 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 $870 per night (USD)VRBO
From $299 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 $299 per night (USD)VRBO
From $479 per night (USD)VRBO
Cozy Home with Hot Tub, Lots of peace /quiet with Mountain views Near Woodstock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Olivebridge is a quiet and beautiful area! Close to the best hiiing trails in hudson valley! My home features a Jacuzzi ...
From $479 per night (USD)VRBO
From $150 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 $150 per night (USD)VRBO
From $501 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 $501 per night (USD)VRBO
From $432 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 $432 per night (USD)VRBO
From $1251 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 $1251 per night (USD)VRBO
From $436 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 $436 per night (USD)VRBO
From $233 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 $233 per night (USD)VRBO
From $276 per night (USD)VRBO
Peaceful, Secluded Olive Star 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 $276 per night (USD)VRBO
From $938 per night (USD)Expedia
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 $938 per night (USD)Expedia
From $198 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 $198 per night (USD)VRBO
From $640 per night (USD)Expedia
Stylish Mountain House with Reservoir Views, Near Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy year-round inspiration and comfort in this modern, stylish, eco-conscious home with spectacular views of the Ashok ...
From $640 per night (USD)Expedia
From $403 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 $403 per night (USD)VRBO
From $467 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 $467 per night (USD)Expedia
From $212 per night (USD)VRBO
Modern 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 $212 per night (USD)VRBO
From $483 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 $483 per night (USD)Expedia
From $600 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 $600 per night (USD)VRBO
From $593 per night (USD)Expedia
NEW: Atomic Ranch - MCM One Level in Olivebridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Krom Ranch is a beautifully restored, single-level retreat in the charming hamlet of Olivebridge—perfectly positioned fo ...
From $593 per night (USD)Expedia
From $763 per night (USD)VRBO
NEW TO VRBO - Catskills Cabin Surrounded by Mountain Views and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We newly joined the VRBO community this week but have a 4.96 rating with over 200 stays on another major platform! Ques ...
From $763 per night (USD)VRBO