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

Guesthouse in Woodstock

4.86 out of 5 average rating, 831 reviews

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

Jan 20 – 27

R2,362 ZAR per night

Guest favorite

Home in West Shokan

4.87 out of 5 average rating, 116 reviews

Watson House 1850

1850 Watson House near the Catskill high peaks, with the beautiful sound of the nearby Bushkill Creek. Spacious, clean, peaceful. Fast reliable WIFI. Big stone fireplace. Two roomy bedrooms, screened porch, and a picket-fence. AC, fire pit with adirondack chairs. A comfortable mix of art and wooden mid-century minimalism. The house is in a beautiful natural area while a short drive to town, restaurants, farm stands. Favorite summer spot – the sunroom with french doors open to the garden!

May 17 – 24

R4,057 ZAR per night

Guest favorite

Cottage in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

Aug 17 – 24

R2,324 ZAR per night

Guest favorite

Cabin in Napanoch

4.94 out of 5 average rating, 248 reviews

Serene Catskill Mountain Top Retreat - Denning

2 bedroom Catskill Mountain top cabin located on 30 private and pristine acres. Ideal for the nature lover in search of privacy, relaxation and access to Catskill hiking trails, waterfalls and area ski attractions (Hunter Mountain) and nature parks (Minnewaska/Mohonk). Cabin has two full beds and a sleeper loft with another full bed(ideal for children or an extra guest). About two hours from New York City and 40 minutes from the restaurants & attractions of Woodstock and New Paltz.

Mar 13 – 20

R2,762 ZAR per night

Guest favorite

Home in Kingston

4.96 out of 5 average rating, 260 reviews

Country Elegance with Beautiful Catskill Mt. Views

Great location, 20 minutes from Woodstock, Kingston, Stone Ridge, High Falls. 2 hours north of New York City. Located on a cul-de-sac with an incredible view of High Point Mt. with breathtaking sunsets minutes from the Ashokan Reservoir! We supply wood for the wood-burning stove + baseboard heat. We have Apple TV, Espresso coffee machine, French Press, Pour-Over, Blender, Magic Bullet, Food Processor and Toaster Oven. People from all backgrounds are welcome! Eco-friendly!

Feb 19 – 26

R3,583 ZAR per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 744 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 7 – 14

R2,074 ZAR per night

Superhost

Guesthouse in Hurley

4.86 out of 5 average rating, 421 reviews

Art, Books, and Mountains

Spacious, clean, classy, private studio between Woodstock and Kingston- rural environment on 9 acres, decorated with my art. Location central to everything! As an artist, I value beautiful environments. Being a traveler, I know the value of returning home to a space that is beautiful and homey. I've stocked it with reading material, Roku TV, comfortable queen bed, microwave, fridge, coffee-maker. Extra single mattress available - $50 fee payable upon arrival .

Oct 13 – 20

R1,960 ZAR per night

Guest favorite

Cabin in Boiceville

4.94 out of 5 average rating, 214 reviews

Catskills Mountain River Dream House

*Art-filled c. 1910 Cottage w/ wrap-around porch *A self-contained natural wonderland for grownups, kids, and dogs *Riverfront w/ private swimming hole: trout fishing, swimming, tubing on site *Huge back yard w/ meandering brook, seasonal cascade, surrounding woods *Badminton court *Mature perennial gardens *Fire pit *Hybrid Charcoal/Gas Grill *Hot outdoor shower overlooking Gardens *Minutes walk to Ashokan Reservoir Rail Trail (run/bike/stroll)

Nov 22 – 29

R5,291 ZAR per night

Guest favorite

Apartment in Rosendale

4.96 out of 5 average rating, 201 reviews

Rosendale Trestle View

Enjoy views from your upstairs oasis: 1 bedroom, office, kitchen, & bath. Stay coooool all summer long with our very quiet mini splits. Slip out your private entrance to hike Joppenbergh. Bring or Rent a bike, ride or walk or even X-country ski the #EmpireTrail, the Rosendale trestle and Wallkill Rail-trail. View the trestle and walk 5 minutes to the trail from the house. Walk to local eateries, and cinema, or just relax by the river.

Apr 7 – 14

R2,383 ZAR per night

Guest favorite

Guesthouse in Mount Tremper

4.91 out of 5 average rating, 326 reviews

Cozy Catskill Cottage Perfect Getaway for Two

NEWLY RENOVATED, COZY, CLEAN, PRIVATE AND SECURE Cottage in scenic and peaceful locale. Convenient and easy to find near the town of Phonecia, NY. 100 PACES to the ESOPUS RIVER and its trout fishing, trail heads and scenic hikes less than a mile away. Close to numerous sophisticated dining and shopping options. Less than 30 minutes to BelleAyre and Hunter Summer Happenings. Perfect for couples who need a weekend country getaway.

Feb 6 – 13

R2,717 ZAR per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 680 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Mar 5 – 12

R2,481 ZAR per night

Guest favorite

Home in Accord

4.97 out of 5 average rating, 117 reviews

The Woods House, 40 secluded acres & speedy wifi!

Private, Secluded, Peaceful! If you’re looking for a rare experience, a week, month or weekend respite —The Woods House is for you! Enjoy the peace! Conveniently located outside the historic village of Stone Ridge, NY, in the Lyonsville, Accord area—close to High Falls, Rosendale, Woodstock, Kingston and New Paltz — yet set in 40 acres of forest, our House in the Woods is blissfully quiet and secluded.

Apr 29 – May 6

R3,523 ZAR per night