Kid-friendly holiday rentals in Olive

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Olive

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

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Guest favourite

Guest house in Accord

4.93 out of 5 average rating, 114 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.

24–31 May

₹7,537 per night

Guest favourite

Guest house in Mount Tremper

4.97 out of 5 average rating, 300 reviews

Artful and Serene Woodstock Getaway

Please read description thoroughly before booking. Relax with a comfortable mix of rustic and elegant in this colorful studio with loft bedroom in the Catskill Mountains of NY. Midway between lovely towns, Woodstock and Phoenicia. Full kitchen and bath, cathedral ceiling, sleeps two adults comfortably. Due to allergies, we do not allow pets. This includes service animals. We use fragrance free laundry detergent. No smoking or vaping. This listing is not suitable for children or infants.

25 Jun – 2 Jul

₹10,176 per night

Guest favourite

Barn in Stone Ridge

4.93 out of 5 average rating, 249 reviews

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.

12–19 Jul

₹11,905 per night

Guest favourite

Cabin in Kerhonkson

4.98 out of 5 average rating, 122 reviews

Lovely Catskill Cabin w/Piano and free firewood

When you truly want to get away from it all, come experience the wilderness of the Catskills. We're nestled next to 30k acres of the Sundown Wild Forest inside the 300k acres Catskill Park, 2 hrs from NYC. Enjoy any of the 3 fireplaces located in and around the cabin after your choice of 8 hiking trails you can take from our doorstep including the cascading pools of the secluded Vernooy Kill Falls. We are the closest Airbnb to the historic Vernooy Kills Falls and its 300-year-old ruins.

3–10 Dec

₹12,070 per night

Guest favourite

Cabin in Kerhonkson

5.0 out of 5 average rating, 308 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!!

29 Nov – 6 Dec

₹11,237 per night

Guest favourite

Cottage in Olivebridge

4.91 out of 5 average rating, 116 reviews

Highpoint House: historic farmhouse on four acres

Built in 1790 and fully renovated in 2015, this historic farmhouse is set on four private acres at the foothills of the Catskills. Enjoy the serenity of the extensive lawns, explore the woods that lead up to High Point mountain, or venture out to experience all that the region has to offer. Highpoint House is within a half-hour drive of Kingston, Woodstock, Phoenicia, and just two hours from NYC, making this the perfect, secluded, four season retreat. Registration No: STR-23-16

29 Sep – 6 Oct

₹23,282 per night

Guest favourite

Guest house in Olivebridge

4.96 out of 5 average rating, 226 reviews

Black Olive Cabin in the Woods - Secluded, Tiny

The cabin is nestled into a mossy rock ledge covered with ferns in a secluded part of the Catskills just south of the Ashokan Reservoir. Constructed of large reclaimed hemlock beams and charred cedar siding on the outside, the cabin mixes the old with the new. The open concept design includes high ceilings, hardwood floors, a wood stove, lofted sleeping quarters, a full bathroom, and a kitchen with an induction cooktop and convection oven. It's the perfect weekend getaway.

29 Sep – 6 Oct

₹11,990 per night

Guest favourite

Cottage in Kerhonkson

4.91 out of 5 average rating, 379 reviews

Home Alone Woods

Small and charming cottage in quiet and secluded place surrounded by woods and nature with the hiking trails half a mile away. There is easy access to Hunter Mountain, Minnewaska State Park, Shawangunks, and many hiking trails. This is a perfect getaway for nature and outdoor enthusiasts, bikers, hikers, climbers, and skiers or people who look for peace and tranquility in the woods.The kitchen is equipped with cooking essentials such as pots, pans, and utensils.

31 Jul – 7 Aug

₹13,332 per night

Guest favourite

Cottage in West Shokan

4.91 out of 5 average rating, 160 reviews

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. Dogs considered, just ask.

24 Apr – 1 May

₹25,420 per night

Guest favourite

Guest house 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.

6–13 Feb

₹12,013 per night

Guest favourite

Cabin in Olivebridge

4.93 out of 5 average rating, 429 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

29 Nov – 6 Dec

₹15,221 per night

Guest favourite

Cottage in Shokan

4.9 out of 5 average rating, 241 reviews

Catskills 2 br Cottage

This sunny, 2br 1.5 bath cottage is perched on a mountainside, so you can enjoy the seasonal view of the Catskill Mountains and the Ashokan Reservoir as you bask in the warmth of the woodstove and cook great meals in the fully equipped kitchen. Located on a quiet, dead-end road, it is close to Woodstock and Phoenicia and less than 30 minutes from skiing at Belleayre. Just a 2-hour drive from NYC!

26 Jul – 2 Aug

₹11,121 per night