Vacation rentals in Olivebridge

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Olivebridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1

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

ValueLocationAccess

4.99 out of 5 average rating, 185 reviews

Top guest favorite

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

FamilyValueCheckout

4.99 out of 5 average rating, 159 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.

FamilyValueLayout

4.94 out of 5 average rating, 339 reviews

Top guest favorite

Home in Kerhonkson

Fall Farmhouse: Private, Firepit & Fireplace

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

FamilyLocationWalkability

4.97 out of 5 average rating, 193 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

ValueFamilyHiking

4.96 out of 5 average rating, 272 reviews

Top 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.

FamilyLocationSkiing

4.95 out of 5 average rating, 217 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

FamilyLocationSolo travel

4.9 out of 5 average rating, 302 reviews

Guest favorite

An open living area is highlighted by vaulted wooden ceilings, large windows, and sliding glass doors leading to the deck. A cozy wood-burning stove offers warmth, while comfortable seating arrangements and a television are also present, creating a functional and inviting space.

Cottage in West Shokan

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Equipped with a backup generator. Dogs considered, just ask.

FamilyLocationHeating

4.92 out of 5 average rating, 189 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

ValueLocationPets

4.97 out of 5 average rating, 173 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

FamilyLocationHeating

4.98 out of 5 average rating, 57 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

FamilyValueHiking

4.94 out of 5 average rating, 600 reviews

Guest favorite

An outdoor fire pit is surrounded by wooden chairs, creating a cozy atmosphere for gatherings. The setting sun casts a warm glow over the home, visible in the background, with trees framing the scene and outdoor lighting enhancing the tranquil ambiance.

Home in Olivebridge

Olive Woods House - Catskills Mountain Views

The Olive Woods House is located in the heart of the Catskills - a two bed, two bath, light and airy cottage cradled in a hill of ferns with a valley to mountain vista. The home features thoughtfully appointed rooms to ensure a comfortable stay and plenty of outdoor spaces to slow down, enjoy the fresh air and truly take a break from busy lives. Town of Olive registration number: STR-22-25 Follow us @OliveWoodsNY

FamilyLocationQuiet

5.0 out of 5 average rating, 94 reviews