Vacation rentals in Olivebridge

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Top-rated vacation rentals in Olivebridge

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Top guest favorite

A charming 1950s cottage exterior features a rustic wooden facade with a welcoming front door highlighted by a window and shutters. Lush greenery surrounds the entrance, with flowerbeds and decorative stones adding character. A gravel path leads to the main door, creating a cozy appeal.

Guesthouse in Olive

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

LocationValueTV

4.99 out of 5 average rating, 182 reviews

Top guest favorite

An open living area features hardwood floors and a ceiling fan. Multiple artworks adorn the walls, with two french doors allowing natural light to enter and providing access to an outdoor deck. A cozy seating arrangement includes a red sofa and a circular coffee table with floral decor.

Barn in Stone Ridge

Hudson Valley Botanical Garden Rental

Located in Upstate New York on the edge of our Botanical Garden in the Lower Hudson Valley the "Barnette" is for nature lovers. This newly built repurposed barn is perfect for relaxing, exploring nature, and getting away from it all. Nearby are lots of hiking, rail trails, and farms. We are within driving distance of the Mohonk Mountain House, Minnewaska, Catskill Mountains, and a 2 hour drive from Manhattan. For winter enthusiasts there’s places to snowshoe, ski, and hike 20-60 minutes away.

ValueFamilyCheck-in

4.94 out of 5 average rating, 335 reviews

Top guest favorite

Home in Kerhonkson

Top 5% - Private & Modern Farmhouse, BBQ, 2hrs NYC

Super private, pet-friendly 13 acre solar powered*, modern farmhouse 2 hours from NYC in Catskills. ✔ Large backyard w/ firepit ✔ Dogs allowed** ✔ 229Mbps wifi ✔ Screen-in porch w/ outdoor dining ✔ 65” Smart TV with Apple TV in living room ✔ 50” Smart TV with Apple TV in guest bed ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Onsite parking 10 mins → Vernooy Falls 20 mins → Minnewaska State Park, Mohonk Preserve & Ashokan Rail Trail

FamilyLocationWifi

4.98 out of 5 average rating, 190 reviews

Top guest favorite

An airy kitchen area features high wooden beams and pendant lights above a marble-topped island. Stools are placed along one side, while large windows allow natural light to illuminate the space, creating a bright and open atmosphere.

Home in Olivebridge

Catskills Hudson Valley Family Hideaway

A big house with modern amenities that’s cozy as a cabin in the woods! It's your perfect base for exploring the Catskills and Hudson Valley, minutes from Ashokan reservoir, or a short drive to Woodstock, Kingston, and scenic nearby towns. Our 4-BR, 2-bath house is set back from the road, with privacy in every direction. Huge living area with projector, well-equipped kitchen, a large yoga/WFH space, plus acres of outdoor space with hammock and newly-built patios, firepit, BBQ, and large deck.

LocationFamilyCheck-in

5.0 out of 5 average rating, 84 reviews

Guest favorite

Cabin in Stone Ridge

6 Private, Serene Acres, Firepit, Screened Porch

Unplug, unwind, and reconnect with nature at our peaceful log cabin on 6 private wooded acres in historic Stone Ridge. Less than two hours from Manhattan and minutes from Mohonk Preserve, Minnewaska, the Gunks, hiking, waterfalls, wineries, restaurants, and local farms. Perfect for romantic getaways, peaceful resets, and outdoor adventures, this thoughtfully designed retreat offers comfort, privacy, and room to breathe, slow mornings and cozy nights. IG:@Stillwood_Retreat

LocationValueCheckout

4.96 out of 5 average rating, 272 reviews

Guest favorite

A serene bedroom features a spacious bed adorned with decorative pillows and a soft throw. Nightstands with lamps are situated on either side. Natural light filters through two windows, complemented by light-colored curtains, creating a calm and inviting atmosphere.

Guesthouse in Olivebridge

The Ashokan Guest House

This newly renovated guest house is attached to a 120 year-old farmhouse which originally housed the workers building the Ashokan Reservoir. This quiet refuge sits on a lovely 3-acre lot in Catskill Park within .5 mile of Ashokan Reservoir. An outdoor adventure in our beautiful Catskill Mountains awaits any direction you go. This is the perfect location for couples or individuals looking for a retreat (it is not child-proofed). Near Kingston, Woodstock and Stone Ridge.

LocationValueParking

4.95 out of 5 average rating, 212 reviews

Guest favorite

A wooden dining table is set in the kitchen, featuring a welcome sign beside a purple water bottle and a decorative vase filled with fresh flowers. A bag of popcorn sits at the edge of the table, and kitchen appliances are visible in the background.

Home in Stone Ridge

Historic Schoolhouse | Outdoor Shower + Pets OK!

Stay in a charming 1800s schoolhouse tucked into the woods in Stone Ridge. With two bedrooms, plus a private sleeping loft, a wood-burning stove, and modern amenities, it’s a cozy home base for exploring the Hudson Valley and Catskills. *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

LocationValueSkiing

4.9 out of 5 average rating, 302 reviews

Top guest favorite

Home in Stone Ridge

Contemporary Stone Ridge Retreat | 6 Private Acres

Escape to the Hudson Valley in this bright contemporary retreat on 6 private acres along one of Stone Ridge's most scenic roads. This single-level home offers 3 bedrooms, including a primary ensuite, cathedral ceilings, a wood-burning fireplace, screened porch, fire pit, and thoughtful luxury touches throughout. Minutes from hiking, farm stands, restaurants, and charming Hudson Valley towns. Dog friendly ($125 fee per dog; no cats due to allergies). STR 2025-01

ValueFamilyCondition

4.97 out of 5 average rating, 173 reviews

Top guest favorite

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

ValueLocationIndoor spaces

4.95 out of 5 average rating, 370 reviews

Top guest favorite

The exterior of the mid-century modern cottage is displayed, featuring a light-colored facade with a prominent red door. Lush greenery surrounds the property, and a well-maintained lawn is visible, offering a serene ambiance against the backdrop of trees.

Home in Olivebridge

Olive Star Cottage & Garden (Pet Friendly)

Wake up in this private tranquil retreat. The cozy, 2 bed/1 bath mid-century modern cottage is located on over two acres of land boasting a back deck with BBQ, king-size hammock, fire-pit and dining area, lovely views, a lawn and woods for a great place to enjoy the outdoors. PLEASE NOTE: This is a prior Airbnb plus listing (122 reviews - 4.93 rating). Due to a change of host a new listing had to be created. Town of Olive rental registry #: STR-22-28

LocationFamilyCheck-in

4.98 out of 5 average rating, 56 reviews

Guest favorite

A charming blue cabin is covered with a layer of fresh snow, creating a wintery scene. The front porch features a railing and steps leading to the snowy yard. Warm light glows from the windows, hinting at a cozy interior amidst the serene, wooded landscape.

Cabin in Olivebridge

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

ValueFamilyGetting around

4.94 out of 5 average rating, 599 reviews

Top guest favorite

The exterior of a craftsman home is showcased among lush greenery and mature trees. A gravel driveway leads to a porte cochere, providing covered access. Surrounding wildlife-friendly gardens feature tall grasses and wildflower seedlings, contributing to the natural serenity of the setting.

Home in Accord

Private Retreat b/t Mohonk & Woodstock - Sleeps 8

Come enjoy our mountain retreat! This secluded 3000-square-foot craftsman home sits on 5.5 wooded acres set far off of a quiet road in Accord. There are three large bedrooms with queen beds (all brand new top-of-the-line memory foam) and a media room with a door that has a queen pull out couch. Additionally, there are two twin XL rollaway beds (also memory foam) for your use. All in all, the house comfortably sleeps 8.

LocationFamilyCondition

4.97 out of 5 average rating, 108 reviews