Kid-friendly vacation rentals in Olive

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Top-rated kid-friendly rentals in Olive

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

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Guest favorite

Guesthouse 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.

May 17 – 24

€ 95 per night

Guest favorite

Guesthouse 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.

Jan 1 – 8

€ 127 per night

Guest favorite

Guest suite in Kerhonkson

4.95 out of 5 average rating, 128 reviews

Private Apt. in Vintage House steps to Kerhonkson.

Private sunlit upstairs apt. features magical views of The Catskills. Pets are welcome ($25 fee). One room is a master bedroom with a workspace, TV and huge closets. Second room has a full kitchen (gas stove, fridge/ freezer, sink) large table, sofa that folds out to a full size bed. Use of fire pit, back yard, cafe size tables, outside chairs for your convenience. Unlimited free access to Minnewaska State Park, (save $10 fee). The house is walking distance to town and the Rail Trail. Welcome!

Oct 17 – 24

€ 75 per night

Guest favorite

Cottage in Accord

4.88 out of 5 average rating, 216 reviews

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

May 11 – 18

€ 88 per night

Guest favorite

Barn in Stone Ridge

4.93 out of 5 average rating, 247 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.

Dec 5 – 12

€ 164 per night

Guest favorite

Cabin in Kerhonkson

5.0 out of 5 average rating, 307 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!!

Jun 18 – 25

€ 141 per night

Guest favorite

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

Feb 2 – 9

€ 299 per night

Guest favorite

Guesthouse in Olivebridge

4.96 out of 5 average rating, 225 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.

Sep 27 – Oct 4

€ 148 per night

Guest favorite

Home in Kingston

4.96 out of 5 average rating, 258 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!

Jul 8 – 15

€ 169 per night

Guest favorite

Chalet in Olivebridge

4.98 out of 5 average rating, 124 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Jun 5 – 12

€ 537 per night

Guest favorite

Guesthouse in Mount Tremper

4.91 out of 5 average rating, 325 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.

Aug 27 – Sep 3

€ 151 per night

Guest favorite

Cabin in Olivebridge

4.93 out of 5 average rating, 428 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

Oct 28 – Nov 4

€ 182 per night