
Family-friendly vacation rentals in Round Top
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Round Top
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

1930's Cottage charm cozy air cond. near hiking
1 bedroom 1930's guest cottage with a living room. Near many hiking trails. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.

Catskills Mountain Cottage - Near Hunter & Windham
The Mountain Cottage is a cozy, thoughtfully-designed home in the heart of the Great Northern Catskills, perched on a scenic hill surrounded by an acre of tall, whimsical trees. Only 2.5 hours from NYC, 20 minutes to Windham Mountain, and 25 minutes to Hunter Mountain. It is centrally located to renowned hiking trails, mountain biking, skiing, the Kaaterskill Falls, antique shopping, local apple picking, and excellent coffee, breweries, and vineyards to be enjoyed throughout the four seasons!

La villa Catskills: 1 Bedroom Apt
Welcome to our home nestled in Catskill Park! We are 20 min to Windham Mnt, 10 min to Hunter Mnt, 5 min to Kaaterskill Falls, 3 min to North South Lake & plenty Catskill gems. Take in nature at our 2 acre property & enjoy the views of Upstate NY, all year round! Relax at a family-friendly stay or romantic getaway after a hike or day at the slopes. Grill with scenic mountain views from a private balcony or enjoy a toasty fire pit by the fountain lake, under the stars. #LaVillaCatskills on IG

Unique Tiny House Glamping in the Catskills
Looking for the perfectly romantic glamping getaway? This stunning handcrafted hut was designed by my Buddhist mother for a meditation retreat, and to commune with nature. With unique timbered walls and ceilings, a wood-burning stove (the only heat source), rustic stone detailing on the walls and large glass windows, you'll feel like you're living in the woods, but with the comfort of the indoors. Please note that this is an off-grid camping cabin without water, but there is electricity.

Hideaway Windham/Hunter Fireplace, Snow & Skiing
Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Tomte Cottage in the Catskills!
Stay in the heart of the Catskills! 2 Bedroom Cottage with private entrance. One bedroom has a queen bed the other a twin/full bunk bed, suited for up to 5 guests! Cottage has full kitchen and bath w/shower. Wi-Fi and a 50 inch smart tv. Located 18 minutes to Windham and 30 to Hunter for skiing or snowboarding. Whether you are looking for a quiet weekend retreat or family weekend skiing trip, hiking or just exploring, this is the place for you! Self check in for your convenience.

🏔O'Clarke Mountain House - The Catskills
Enjoy a slice of hosts (Bridgitte and Kevin's) ideal Catskill Mountain vacation rental. This 2bd 2ba apartment has an outstanding kitchen, bathrooms, cozy living room, and a perfect dining table to enjoy all your meals. This is our first home, and we will be your neighbors living on the other side of the duplex, we will respect your privacy and let you enjoy your well-earned time away from home. We hope to introduce you to our favorite shops, hikes, and restaurants nearby.

b/w Hudson&Hunter, a Catskill Unit Made for Snugs
Welcome to the Catskills and rest up in this calm, small, and stylish space! We recently rebuilt the entire interior of an old brick building and imagined the first floor (*** the entrance is at the back of our house***) as a guest unit for our friends & family during visits. When we do not have friends & family visiting, we are offering this space to you! We are architects by training and have placed our aesthetic energy in making this unit modern but also cozy.

Catskill Village House - Studio w/ Private Terrace
Featuring it’s own courtyard entrance, shared garden, and private balcony, the Terrace Studio combines natural and airy accents with custom vintage flairs and original artwork to create an ideal and intimate space perfect for a couple or solo traveler. The room includes a private bath with claw foot tub and shower, custom built kitchenette and dining area. Custom queen mattress (featured at Four Seasons NYC), organic cotton sheets, free WiFi (150mb/12mb) +AC.

Cosy Catskill Casita in the Middle of Village
The Casita is a studio apartment comfortable for solo travellers, couples or just two folks who don't mind sharing a bed! We’ve endeavored to make it a comfortable stay for a weekend or even longer, with all basic amenities, a queen size bed, standing shower bathroom, and kitchenette. Although it is an apartment on the ground floor of my house, you will have your privacy with a separate entrance off of the driveway which is for guest use during the stay.

Gorgeous Tiny House with Mountain View
Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! Ac cools beautifully in summer! The Haven at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill
A really really tiny house ,( smaller than most tiny houses) with a dome patio for viewing the sky. Two hours from NYC, close to skiing (hunter mountain/ Windham, Kaaterskill falls, Woodstock, Hudson, Saugerties. We have - Heat/AC, Queen bed, Hot shower, Flushing Toilet, Kitchenette, Fridge, Towels, linens etc. *Hudson Getaways is a small woman owned business. We offer discounts to our social media followers and to returning guests .
Popular amenities for Round Top family-friendly rentals
Family-friendly home rentals with a hot tub

40-Foot Container Cabin in the Catskills

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Willow Treehouse - secluded, unique, romantic

Woodstock retreat with hot tub and deck with view

Mountain View Chalet: AC, Hot Tub, Firepit, Games

The Mushroom Palace (Hot Tub, Sauna & Cold Plunge)

Modern House with Mountain View @Getawind

Tiny Home A-Frame with Hot Tub & Creek
Family- and pet-friendly home rentals

Cozy Cabin w/ 10 Min Walk to Downtown Catskill

Dog Friendly Uptown Apt Near Stockade + Backyard

Tiny House in Central Catskills

Dutch Touch Woodstock Cottage

Sunset Bungalow-Mt views on 130acre forest & falls

"Far from the Madding Crowd" Cozy Cabin Retreat

Barn House: isolated sheep farm Hudson area

Diamond Notch Trails Tiny Cabin
Family-friendly home rentals with a pool

Windham Condo

Ski & Sauna! Modern Mountain Escape

Sweet Farm Stay

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Eco Cottage in the Woods

Le Soleil Suite - Fire pit, Views 10 Min To Hudson

The Harvest Guest House~ Hidden Gem with Pool

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse
When is the best time to visit Round Top?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $456 CAD | $464 CAD | $431 CAD | $383 CAD | $400 CAD | $464 CAD | $464 CAD | $460 CAD | $468 CAD | $428 CAD | $428 CAD | $456 CAD |
| Avg. temp | -4 °C | -3 °C | 2 °C | 9 °C | 15 °C | 20 °C | 23 °C | 22 °C | 18 °C | 11 °C | 5 °C | -1 °C |
Quick stats about vacation rentals that are family-friendly in Round Top

Total vacation rentals
Explore 30 vacation rentals in Round Top

Nightly prices starting at
Round Top vacation rentals start at $210 CAD per night before taxes and fees

Verified guest reviews
Over 2,060 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Round Top vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Round Top rentals

4.9 Average rating
Round Top stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Minnewaska State Park Preserve
- Windham Mountain
- John Boyd Thacher State Park
- Howe Caverns
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- Taconic State Park
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- Opus 40
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