Family-friendly vacation rentals in Ulster County

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Top-rated family-friendly rentals in Ulster County

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

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Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 346 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Feb 25 – Mar 4

R2,151 ZAR per night

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

Feb 20 – 27

R2,353 ZAR per night

Guest favorite

Cabin 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 21 – 28

R2,315 ZAR per night

Guest favorite

Apartment in Arkville

4.94 out of 5 average rating, 164 reviews

Catskills Hideaway - East

Enjoy the serenity of the scenic Catskill Mountains - relax in a lovely tranquil setting nestled in nature yet minutes from restaurants, galleries & shops. This spacious studio with private exterior stair access in a unique Brick House built in 1965 - the original "Guest House" on a spectacular estate - welcomes guests with breathtaking beauty & magnificent views. Luxurious amenities await in your perfect Hideaway: king size bed, en suite bathroom, kitchen, fireplace, & more!

Jul 30 – Aug 6

R1,657 ZAR 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

R3,098 ZAR per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 742 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 11 – 18

R2,067 ZAR per night

Guest favorite

Townhouse in Saugerties

4.92 out of 5 average rating, 288 reviews

15 min to Woodstock/Saugerties/Hunter (2 bedroom)

Private 2 bedroom home on a wooded lot. Owner lives on site. I live on one side, the other is your unit. Fully stocked kitchen, bathroom and on site parking. All linens and towels provided. 10 minutes from Woodstock & Saugerties. 100 miles from NYC. Located in the Catskills Private yard with fire-pit and BBQ. If you are looking for a weekend away to enjoy the quiet of the outdoors and close to great restaurants, hiking and swimming holes, this is the place.

Aug 6 – 13

R2,412 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.

Sep 8 – 15

R2,287 ZAR per night

Guest favorite

Guesthouse in Mount Tremper

4.91 out of 5 average rating, 324 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.

Sep 5 – 12

R2,710 ZAR per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 678 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.

Apr 22 – 29

R2,469 ZAR per night

Guest favorite

Cottage in Shokan

4.9 out of 5 average rating, 240 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!

Jun 25 – Jul 2

R2,561 ZAR per night

Guest favorite

Cottage in Parksville

4.97 out of 5 average rating, 240 reviews

Rolling River Guest House ~ Cozy & Fun

This charming, private guest house used to be the Rolling River Café, converted into a cozy space with a pellet stove, a queen bed upstairs and futons upstairs and down. Perfect for 1 to 4 guests, such as 2 couples, 3 friends, or a family of 3 or 4. It is private - no sharing with any other guests. It has an open floor plan on both floors.

Sep 16 – 23

R2,153 ZAR per night