
Family-friendly vacation rentals in Smallwood
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Smallwood
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Smallwood family-friendly rentals
Family-friendly home rentals with a hot tub

Pocono Mtn Escape w/ Hot Tub, Pool & Barrel Sauna
The place was amazing and my granddaughter loved it for her birthday. It was nearby everything and the backyard was amazing although the weather wasn’t it nicest to us lol It was an amazing time! We would definitely come back

Secluded Artist's Retreat with Hot tub
We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

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!

Private Catskills Home w. Hot Tub, near Ski Mnt
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

Bushkill Falls Cabin
The place was secluded. the hot tub was perfect. The basement was real chill to hang out on a snowy icy evening

Make it your home away from home
I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!

Renovated Country Cottage w/ Hot Tub & View
Gorgeous house, super clean and tidy inside, with comfy and modern furniture. The hot tub was fantastic, make sure you turn off the lights so you can see the stars! The only other heads up I’ll give is that the way to get in is through the back entrance! We tried the front door for like 5 minutes until the electronic lock blocked us from continuing haha. Great location to get away from the city for a weekend and go hiking. Lots of great trails really close by.

Enchanted Castle - Unique & Charming Getaway
I cant say enough amazing things about this place. It was utterly magical. Eva and Donna were incredible hosts. One of the first things we noticed upon walking in was a nice bottle of wine and some snacks, which was very generous. It was overwhelming the amount of detail and creativity at every corner. Our group of 4 had an absolute blast using the pool table, ping pong, hot tub, sauna, mini golf, and fire pit. Thank you so much for memories that will last a life time. Definitely recommend this place and would love to come back again soon. (Left some water guns in the shed for others to enjoy :D) thank you thank you again.
Family- and pet-friendly home rentals

Stunning Modern Barn minutes from Woodstock 21N195
My family of 4 had a wonderful time! Host was responsive and helpful. We enjoyed this awesome home and would definitely recommend. Kitchen was well stocked and we found the home warm and inviting. The layout is very cool and my girls loved their “castle” bedroom :) thanks so much for hosting!

Nicks Place
We thoroughly enjoyed our stay, the house was neat, clean and well stocked with everything we needed. The location was absolutely beautiful and check in and our procedures were very easy.

Entire lake house to yourself. Great for groups
Beautiful location on the lake. We enjoyed using the kayak, deck, grill, kitchen, and pool table. Excellent communication from Scott. Plenty of room for the whole family. Thank you!

Pet Friendly Cabin Doh-Ray up at 1450 ft
This is the place to go if you want to be immersed in nature. You are definitely in the woods and surrounded by lush green. There is a pond glistening in your view from the back screened in porch. A lovely spot to have a curl up with a good book.!

Serenity Retreat: Mountains, Waterfalls, Comfort
Beautiful quiet private setting. Everything as advertised, clean, and great communication throughout. Would definitely stay there again! Thanks so much for a beautiful stopping place on our travels!

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!

Catskill Mountain Cabin Waterfall Retreat
I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.

Woodstock Secluded Close to Town
This house was perfect for our family with adult children and an old dog; it was clean and spacious, and yet homey. We felt comfortable right away. The view of trees and Overlook Mountain is stunning, and the house is truly secluded, and yet close to town. Simply terrific!
Family-friendly home rentals with a pool

Heated Pool Now OPEN, Lakefront, Hot Tub, Firepit
Fantastic property and location with plenty of amenities! Even with some bad weather our group had a wonderful time. Great fishing too! Jose and Jennifer are extremely professional and responsive. I would definitely stay here again.

Secluded Cabin•Jacuzzi•Pool Table•King Bed•FirePit
The house was very nice and clean! The host was great with communication. The jacuzzi was relaxing and we had a wonderful time

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.

MODERN FARMHOUSE in the WOODS
We had a terrific stay. The house was exactly as advertised.

Arrowhead Lakes Log Cabin Jack Frost,Kalahari
House was awesome , very neat and cozy!!! We will definitely come back soon. Communication with the host was great and smooth. We really enjoy our New Year’s Eve there.

Upstate Modern Scandinavian Barn in the Catskills
Fantastic place. My adult children had a blast playing basketball and tennis. The pool table and piano were thoroughly enjoyed --piano sounded well tuned. Views out of living room are particularly stunning. Hot tub was also great amenity and great after long day. Tons of toys for my grandson to enjoy. We cooked incredible meals and there were plenty of supplies for that. Highly recommend fur faculty reunion or sporty families. Near to everything

FREE Amenity Passes Spacious Sauna Lrg Deck Firepi
Our stay at this property was nothing short of excellent! From the moment we arrived, we were impressed by the beautiful ambiance and attention to detail throughout the home. Every room was comfortable, well-appointed, and loved by everyone in our group. The property was clean, inviting, and had everything we needed for a relaxing getaway. The host was responsive and accommodating, ensuring our stay was seamless. We truly enjoyed every moment and would highly recommend this Airbnb to anyone looking for a fantastic place to stay. We can’t wait to return!

Lovely Creekside w pool/sauna near Woodstock
We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.
Quick stats about vacation rentals that are family-friendly in Smallwood
Total rentals
90 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
4.3K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi
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- Hunter Mountain
- Mountain Creek Resort
- Kalahari Resorts
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Bushkill Falls
- Minnewaska State Park Preserve
- Montage Mountain Resorts
- The Kartrite Resort & Indoor Waterpark
- Sunset Hill Shooting Range
- Delaware Water Gap National Recreation Area
- Elk Mountain Ski Resort
- Aquatopia Indoor Waterpark
- Ringwood State Park
- Promised Land State Park
- Resorts World Catskills
- Walkway Over the Hudson State Historic Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- The Country Club of Scranton
- Hunter Mountain Resort
- Sterling Forest State Park
- Camelback Snowtubing
- Villa Roma Ski Resort
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