Family-friendly holiday rentals in Callicoon

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Callicoon family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Olivebridge
4.92 out of 5 average rating, 458 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

AmeliaRating, 5 stars1 month ago
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!
Guest favourite
Cabin in Swan Lake
4.83 out of 5 average rating, 202 reviews

Stunning Mountain Cabin w/ Pool & Hot Tub

NickolasRating, 5 stars1 month ago
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.
Top Guest favourite
Guesthouse in Forestburgh
4.97 out of 5 average rating, 422 reviews

Guesthouse On 1879 Farm. Hot tub and hiking

StacyRating, 5 stars1 week ago
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.
Guest favourite
Cabin in Livingston Manor
4.97 out of 5 average rating, 307 reviews

Experience The Zen House

BethRating, 5 stars1 week ago
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!
Superhost
Cabin in Roscoe
4.93 out of 5 average rating, 228 reviews

Roscoe Retreat

OlkaRating, 5 stars3 days ago
beautiful place, friendly owners, everything you need to disconnect from a crazy world
Guest favourite
Home in Neversink
4.98 out of 5 average rating, 219 reviews

Modern Riverside Retreat with Firepit, Hot tub

Stephanie Rating, 5 stars1 week ago
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!
Guest favourite
Home in Accord
4.96 out of 5 average rating, 141 reviews

Little Minka - Japanese House in the Woods

LekanRating, 5 stars1 month ago
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!
Guest favourite
Cabin in Wurtsboro
4.93 out of 5 average rating, 101 reviews

Catskills cabin over waterfall w/ views & hot tub

Ana PaulaRating, 5 stars1 month ago
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

Guest favourite
Cottage in Woodridge
4.85 out of 5 average rating, 121 reviews

Outlier Inn Cottage on Farm Upstate Catskills

LindseyRating, 5 stars2 months ago
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!
Guest favourite
Cabin in Narrowsburg
4.96 out of 5 average rating, 100 reviews

Catskill's Le Petite Cabine on the River

GaryRating, 5 stars4 months ago
Host was very accommodating and generous . Please brings you back to simpler day just what we needed to get away from the city
Top Guest favourite
Bungalow in Margaretville
4.87 out of 5 average rating, 115 reviews

Tranquil Paradise With Lake Views

ZoeRating, 5 stars1 week ago
It's a magical location with a beautiful forest and reservoir view.
Guest favourite
Barn in Highmount
4.97 out of 5 average rating, 151 reviews

The Catskills Red Barn near Belleayre

VanessaRating, 5 stars4 months ago
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!
Guest favourite
Cabin in Arkville
4.97 out of 5 average rating, 329 reviews

Solace: perfect for all seasons; near Belleayre Mt

JericaRating, 5 stars1 month ago
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!
Guest favourite
Home in Margaretville
4.91 out of 5 average rating, 127 reviews

Modern Stylish Cozy Vibe near Skiing

EmilyRating, 5 stars1 month ago
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.
Superhost
Home in Margaretville
4.89 out of 5 average rating, 223 reviews

Running Horse Cottage

GrayceRating, 5 stars1 month ago
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!
Superhost
Cabin in West Kill
4.86 out of 5 average rating, 318 reviews

Mink Hollow Cottage very comfy wilderness retreat

NancyRating, 5 stars5 days ago
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

Guest favourite
Home in Bushkill
4.91 out of 5 average rating, 118 reviews

Sale: June 27-28, Pvt Heated Pool OPEN, Hot Tub

ShevaRating, 5 stars3 weeks ago
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!
Top Guest favourite
Condo in Vernon Township
4.91 out of 5 average rating, 267 reviews

206 · Renovated Chic Premium 1 bdrm

EfrainRating, 5 stars4 days ago
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.
Superhost
Home in Bushkill
4.85 out of 5 average rating, 296 reviews

Summer Fun•Pool•Jacuzzi•Game Room•King Bed•FirePit

BrentonRating, 5 stars2 weeks ago
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.
Superhost
Cabin in Walton
4.83 out of 5 average rating, 132 reviews

Catskills Cabin Off the Grid Experience

MichaelRating, 5 stars20 months ago
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.
Guest favourite
Condo in Vernon Township
4.95 out of 5 average rating, 192 reviews

Comfy Studio at Mountain Creek Resort

ErinRating, 5 stars1 week ago
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.
Top Guest favourite
Home in Tobyhanna
4.8 out of 5 average rating, 130 reviews

Cozy home for 10 ~ Private pool, BBQ, fire pit

EsteeRating, 5 stars4 months ago
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.
Guest favourite
Condo in Vernon Township
4.94 out of 5 average rating, 852 reviews

Appalachian Lodge Top Floor w/views

GilbertRating, 5 stars3 days ago
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.
Superhost
Home in Tobyhanna
4.9 out of 5 average rating, 215 reviews

#1 Lakefront Hot Tub, Pool, Boat, Fire Pit, Casino

RichardRating, 5 stars1 month ago
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