Family-friendly vacation rentals in Olive

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Top-rated family-friendly rentals in Olive

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

An open living area is highlighted by a wood-burning stove, providing warmth to the space. A dining table with chairs is positioned adjacent to large windows, allowing natural light to fill the room. A globe and a cozy blanket add decorative touches.

Cottage in West Shokan

4.96 out of 5 average rating, 184 reviews

Catskills Getaway w/AC on 3 Acres near Woodstock

You have the whole house and three acres to enjoy. The two bedrooms are upstairs, with skylights and a bright, airy feel to them. The wood burning stove is an awesome way to make things cozy. There's also a firepit and grill you're welcome to use. Guests have complete access to the home and three-acre property. The garage on the property is inaccessible by guests. We're available to contact anytime. Hike, ski, swim, bike, do yoga, or whatever comes to mind— all is possible in the Catskills. The Ashokan reservoir bike/walk path is a few miles down the road. Not far the other way is Marty's Mercantile for coffee, lunch, and basic supplies. There's plenty of parking in the driveway. Don't expect to Uber while up here. Walk, bike, or ride a horse instead. :) There's plenty of parking in the driveway.

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

4.99 out of 5 average rating, 136 reviews

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

Guest favorite

A cozy seating area features a light-colored sofa and a red sofa, both positioned around a wooden coffee table. A modern area rug is laid beneath them, while strategically placed lights illuminate the space from above.

Guesthouse in Accord

4.93 out of 5 average rating, 164 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.

Guest favorite

An exterior view of a tiny cabin nestled among tall trees, featuring a wooden deck and a distinct rustic façade. The pitched metal roof reflects light, while the welcoming entrance is framed by the surrounding nature.

Cabin in Kingston

4.93 out of 5 average rating, 249 reviews

Cabin 192

No cleaning fee and no 2-night minimum! Cabin 192 is a tiny home glamping experience located in lovely Kingston, NY. Cabin 192 takes you back to 1992 with: a vhs collection of classics, a Super Nintendo, Sega, and other fun activities. Warm and toasty in fall and winter and cool in summer you’re always comfortable at Cabin 192. Enjoy smores by the fire surrounded by trees in nature while also being able to enjoy a vibrant uptown district a 9-minute drive away! Minnewaska and Woodstock nearby!

Top guest favorite

A small dining area is seen with a round wooden table and a patterned chair. A large window offers a view of the outdoors with trees and a rustic shed visible beyond. A piece of artwork is displayed on the wall, enhancing the cozy atmosphere.

Guest suite in West Shokan

4.95 out of 5 average rating, 169 reviews

Stylish and Cozy Mountain Retreat

Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

Top guest favorite

A spacious studio area features wooden beams above, with a large artwork displayed on the back wall. The floor is adorned with various rugs, and a kitchenette is visible, equipped with essential appliances. A chair is situated near a curtain-draped area, enhancing the room's functionality.

Home in Shokan

4.97 out of 5 average rating, 138 reviews

West Wing - a unique private space w/deck

This unique studio space with private entrance is a recent addition to our charming home, located on a quiet private road in the village of Shokan. Situated within minutes of the Ashokan Rail Trail, this bike and walking trail offers dramatic vistas of the Ashokan Reservoir. Woodstock & Phoencia with their stores, galleries and restaurants are only 15 minute drives . Local recreation includes hiking trails, kayaking and for those looking for relaxation there are renowned spas.

Top guest favorite

A rustic Finnish cabin is seen nestled among trees, featuring a slanted wooden roof and a spacious deck. Adironack chairs are placed on the deck, complemented by a green umbrella. A stone garden borders the deck, enhancing the natural surroundings.

Cabin in Rochester

4.99 out of 5 average rating, 381 reviews

The Metsämökki - A Finnish Cabin in the Woods

The Metsämökki is a small Finnish cabin in the foothills of the Catskill Mountains. Originally a sauna that was shipped here from Finland. We renovated it to a tiny house that offers complete privacy. Enjoy the babbling brook while sitting on the deck and taking in the surrounding nature. We're not offering high-tech or glamour but this cabin is a beautiful retreat from the busy city. **Check out our new midweek discounted rates and enjoy a little extra time for a great price!!

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

4.94 out of 5 average rating, 171 reviews

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.

Guest favorite

The cabin exterior is set against a backdrop of tall trees, with a wooden deck providing access to a well-maintained backyard. Outdoor furniture is arranged on a stone patio, surrounded by a lush green landscape, creating a serene and secluded atmosphere.

Cabin in Stone Ridge

4.96 out of 5 average rating, 245 reviews

Modern Cabin Getaway: Idyllic, Secluded, Serene

Escape to our charming log cabin, nestled on a serene 6-acre property surrounded by the soothing sounds of nature and scenic beauty. Though perfectly private, the cabin is conveniently located near markets, shops, restaurants, and just a short distance to the heart of town. An ideal escape Less than 2hrs from NYC. Hiking, nature trails, swimming holes, skiing, local farms, wineries, reservoirs, waterfalls, historic sites, all await you. IG:@griffithhousecabin

Top 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

4.94 out of 5 average rating, 537 reviews

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

Top guest favorite

An aerial view of the villa showcases its spacious layout surrounded by greenery. The large deck is visible, along with a fire pit area that features circular seating. The property is bordered by trees, emphasizing its connection to nature.

Villa in Kerhonkson

4.97 out of 5 average rating, 283 reviews

Peaceful Forest Villa Escape w Private Yoga Studio

Boutique forest retreat with private yoga studio, 110″ home theater, Casper and Nectar beds, EV charger, Moroccan tea room, fast Wi-Fi, and smart TVs. Enjoy the premium kitchen, deck with grill and string lights, fire pit with Adirondack chairs, orchard, trails, and private creek. Designed for wellness, creativity, family retreats, or remote work in nature—near Minnewaska State Park in the scenic Hudson Valley.

Superhost

A view from the cabin reveals a queen mattress framed by sheer curtains. Outside, red chairs encircle a stone firepit, with expansive mountain views visible in the distance. Natural light floods the space, enhancing the connection to the outdoor environment.

Campsite in Accord

4.95 out of 5 average rating, 495 reviews

Canyon Edge off - grid Bungalow

The ideal perch to reflect, connect, and participate in nature's beauty. originally placed and built by H. Dutton, and recently revived, this unique structure blends pure nature with simple comfort. Sitting canyon side, you sleep beneath the canopy and wake to the mountains of the Hudson Valley.