
Family-friendly holiday rentals in Callicoon
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Callicoon
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Callicoon family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain-Top Catskills Getaway Cabin w/hot tub
We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!

Stunning Mountain Cabin w/ Pool & Hot Tub
This A-frame escape was exactly what I needed — the perfect break from the city. The place is beautifully designed, cozy, and filled with thoughtful touches. The jacuzzi was absolutely incredible, especially under the stars at night, and the A-frame structure made the whole stay feel like a peaceful retreat.

Guesthouse On 1879 Farm. Hot tub and hiking
Hidden gem. Really appreciated the countryside accommodation. The hot tub was nice and hot and we enjoyed a fire right after. The stores were in a close enough proximity if needed. My fiancé was skeptical as it’s right next to another property but we had are own space and we were not disturbed. Also we enjoyed the fresh eggs and being able to bring our fur babies.

Experience The Zen House
We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!

Roscoe Retreat
beautiful place, friendly owners, everything you need to disconnect from a crazy world

Modern Riverside Retreat with Firepit, Hot tub
Great home right on the neversink river! Really enjoyed our stay Father’s Day weekend and appreciated the clear instructions and how clean the hot tub was! Appreciate it!

Little Minka - Japanese House in the Woods
The Little Minka was everything that Daniel said it would be. A beautiful, peaceful, quiet, cozy home with an amazing minimalist aesthetic. Definitely a great place for a weekend getaway if you’re looking for a break from the hustle and bustle of the city. Would recommend and look forward to booking again!

Catskills cabin over waterfall w/ views & hot tub
It is clear Adam and Chrissy take care of this place like their own home. I cannot emphasize enough how wonderful this place is. Perfectly equipped, yet doesn’t feel cluttered. Cozy, tasteful, full of wonderful little details, clear instructions and good vibes overall. Location is amazing and perfect for days of reflection / retreat in the mountains. Has all you need in the kitchen, plenty of books, board games, movies, records, even Atari and an AMAZING outdoor spa. Best of all is the water stream running below: natural forest + running water sounds - not even headspace can give you this to perfection. Outdoor seating area also lovely. I felt at home from beginning to end. Hosts incredibly responsive and helpful. Can’t wait to return !
Family- and pet-friendly home rentals

Outlier Inn Cottage on Farm Upstate Catskills
We enjoyed the lovely cozy, private cottage with our family. It was a pleasure to have the animals nearby for the kids to interact with, a safe environment to roam in the woods, and very convenient to have the farm shop a few steps away for local eggs, meats, etc. The cottage was stylishly modern with a clean aesthetic and modern conveniences. Josh was very accessible via text/phone and checked in with us during our stay. We enjoyed ourselves thoroughly and would recommend to nature lovers, families, and those looking for a getaway in the woods!

Catskill's Le Petite Cabine on the River
Host was very accommodating and generous . Please brings you back to simpler day just what we needed to get away from the city

Tranquil Paradise With Lake Views
It's a magical location with a beautiful forest and reservoir view.

The Catskills Red Barn near Belleayre
We had a lovely time at Blythe's place. The house was clean, cozy and so close to Bellayre mountain, which was perfect for our ski trip. Would definitely stay there again!

Solace: perfect for all seasons; near Belleayre Mt
My boyfriend and our 2 pups enjoyed our time here! The place was mostly stocked with what we needed (no lighter for fire pit or coffee filters that we could find (but it rained and k-cups were provided), which neither are a big deal, but things we didn’t think to pack - so pack those if you’d need them!), it was clean, and we enjoyed the location for hiking / fishing and good food! We’d stay here again!

Modern Stylish Cozy Vibe near Skiing
My family and I had a wonderful time here even in the rain! It’s so cozy and beautiful. We had a blast sitting by the fire to make s’mores. The kids had lots of space to run and play too! The Mountain View was everything you could ever want. I never wanted to leave. Host was very responsive when I had a question. It was extremely quiet and beautiful. The towns nearby were also very charming.

Running Horse Cottage
what a great location! we tried cafe mornings, country store & bread alone! visit foodtown for groceries and charcoal- and you don't have to leave this beautiful location! if you you do a lot of hikes to bring your dog too!

Mink Hollow Cottage very comfy wilderness retreat
I loved my stay. Perfect cozy cottage to escape the city. Extremely quiet and peaceful. The house had everything you need and plenty of beautiful hikes nearby. I would definitely come back
Family-friendly home rentals with a pool

Sale: June 27-28, Pvt Heated Pool OPEN, Hot Tub
Such a beautiful spot on the lake!!! We had the most beautiful weekend, the kids loved he pool and the boats, nothing was missing! We would have stayed another week! Jennifer and Jose answered all our messages within a few minutes and were super accommodating. We will definitely be back!

206 · Renovated Chic Premium 1 bdrm
Everything was exactly as was stated and it met the expectations and more. Would recommend anyone to stay and if I ever return will definitely rebook.

Summer Fun•Pool•Jacuzzi•Game Room•King Bed•FirePit
Spent a weekend here with friends and had an awesome time. Yevgeniy was extremely accommodating, and responded to any questions very quickly. I would 100% come back.

Catskills Cabin Off the Grid Experience
Had a great time at the cozy cabin. It's a cabin but still has some nice amenities. Location is somewhat close to road, you can hear occasional cars go by. Still, back by the pond it feels like being away from it all. I had a blast hiking local trails and enjoying the foliage.

Comfy Studio at Mountain Creek Resort
This is the second time we have stayed in one of Kristof’s studios at The Appalachian. As last time, he was great to rent from and very responsive. The studio was perfect for our needs as we were there for a downhill mountain bike race. It was great to be onsite the whole weekend. The studio has everything you need and being on the second floor was nice.

Cozy home for 10 ~ Private pool, BBQ, fire pit
We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.

Appalachian Lodge Top Floor w/views
My wife and I had a great stay at Paul’s place. Very clean and just as described. Look forward to staying again in the future.

#1 Lakefront Hot Tub, Pool, Boat, Fire Pit, Casino
The house and property is perfect! The house was spacious, clean, cozy, and had everything we needed. The lakefront view was absolutely beautiful. The host, Eugene, was amazing—super responsive and so accommodating, which made everything really easy. He answered all of our questions quickly and went above and beyond to ensure we had everything we needed during our stay. We’d definitely come back and highly recommend this spot for families looking for a peaceful and fun getaway!
Quick stats about holiday rentals that are family-friendly in Callicoon
Total rentals
10 properties
Nightly prices starting at
$264 NZD before taxes and fees
Total number of reviews
360 reviews
Pet-friendly rentals
10 properties allow pets
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Destinations to explore
- Pocono Mountains Holiday rentals
- Hudson Valley Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- Philadelphia Holiday rentals
- Jersey Shore Holiday rentals
- The Hamptons Holiday rentals
- South Jersey Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Mountain Creek Resort
- Kalahari Resorts
- Bethel Woods Center for the Arts
- Bushkill Falls
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Delaware Water Gap National Recreation Area
- Sunset Hill Shooting Range
- Montage Mountain Resorts
- The Country Club of Scranton
- Resorts World Catskills
- Promised Land State Park
- Elk Mountain Ski Resort
- Salt Springs State Park
- Lackawanna State Park
- Villa Roma Ski Resort
- Claws 'N' Paws
- Tobyhanna State Park
- Plattekill Mountain