Kid-friendly holiday rentals in Smallwood

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Smallwood family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Narrowsburg
5 out of 5 average rating, 20 reviews

Farm House with Built in pool/jacuzzi open in May

JennRating, 5 stars4 days ago
We came for a quick girls weekend and were pleasantly surprised by how comfortable and homey we felt here. We loved going to the nearby Woodstock museum and a couple of great restaurants in the area. Sadly, the weather wasn’t great but we hope to come back sometime to enjoy all of the amenities that this home and property have to offer!
Superhost
Home in Monticello
4.89 out of 5 average rating, 73 reviews

Grandma's Cottage 2BR+Den

GauravRating, 5 stars2 months ago
We stayed at Grandma’s Cottage for my wife’s birthday, and the experience couldn’t have been better. Originally, we had booked another place, but due to some last-minute issues, we were re-booked here—and honestly, it felt like fate. From the moment we arrived, we fell in love with the cozy, vintage vibe of the house. It’s like stepping into a charming time capsule, with antiques everywhere—record players, an old stove, typewriter, beautiful paintings, unique clocks, and mini art sculptures. Each piece adds so much character! Sheldon (our host) was amazing. Despite the short notice, he kindly accommodated our booking and even stopped by personally to ensure everything was perfect for us. That extra effort meant so much. We’ll definitely be coming back here!
Guest favourite
Home in Coolbaugh Township
4.85 out of 5 average rating, 40 reviews

Cozy Outdoor Firepit-Fireplace-Close to Skiing

EricaRating, 5 stars1 month ago
This house was a great!! My family and I absolutely enjoyed our stay. Jessica was super nice and helpful. Responded quickly which was a huge plus! Over all a great very welcoming home :)
Top guest favourite
Home in Eldred
5 out of 5 average rating, 6 reviews

Dog-friendly Winter Wonderland Retreat

CatherineRating, 5 stars3 months ago
My family & I spend 5 nights in this beautiful home. We had 4 adults with 3 fur babies. We truly enjoyed our stay. I love to cook & Jane’s kitchen was fabulous and very well equipped. The open fire place was perfect. The outside area was ideal for our dogs to run around safely. Short drive to lots of cute towns. I would highly recommend this home for anyone looking for a great country weekend away.
Guest favourite
Home in Phoenicia
4.96 out of 5 average rating, 153 reviews

Hiking and Breweries! Mountain and river views!

LeslieRating, 5 stars2 weeks ago
This was a great house in a lovely spot, can’t wait to come back. It was very comfortable for 4 adults and 2 toddlers. Plenty of room to cook, eat, do puzzles, play, read and relax. The house has a charming, cozy feel and is clean and well maintained. Hosts were kind, helpful and great communicators. Thanks Julie and Pierre - we’ll be back!
Superhost
Home in Monroe
4.85 out of 5 average rating, 142 reviews

Winter Home near Legoland, West Point & Outlet

Ashley + ShaiRating, 5 stars2 months ago
Ruth’s place was perfect for our short getaway to take the kids to learn to ski. Plenty of space and clean. Easy to get to. Would come back next year for some more ski lessons!
Superhost
Home in Tobyhanna
4.88 out of 5 average rating, 25 reviews

NEW! Fun and relaxing home for friends and family!

MichelleRating, 5 stars1 month ago
Lovely home. The kids enjoyed the game room. We had a great time!
Top guest favourite
Home in Woodstock
4.98 out of 5 average rating, 219 reviews

Sweeping mountain views in Woodstock, NY

DanielRating, 5 stars1 month ago
We had a lovely stay! The place was very relaxing, peaceful, and surrounded by nature, yet still close to Woodstock. One of the highlights was seeing a family of deer right outside our window — such a special moment. The hosts were also incredibly accommodating, providing a highchair and pack ’n play for our infant, which made our stay so much easier. We truly appreciated their thoughtfulness and hospitality. Highly recommend to anyone looking for a quiet getaway close to town.

Family-friendly apartment rentals

Top guest favourite
Flat in Wallkill
4.94 out of 5 average rating, 141 reviews

Log Cabin Apartment Great for Outdoor Enthusiasts

MichaelRating, 5 stars3 months ago
We loved our time at this beautiful cottage! We have been to lots of Airbnb’s, and most have been a good experience. This cottage was something more. We both felt instantly relaxed when we walked in the door. It was so cozy and comfortable. We slept great in the comfy bed. The pictures can’t describe the feeling of the place. Warm, cozy, peaceful, inspiring, comfortable, quiet and truly rejuvenating. I will be making a trip to the area again as soon as possible, just to stay in this cabin retreat.
Top guest favourite
Flat in Goshen
4.97 out of 5 average rating, 206 reviews

Historic Horse Barn Sleeps 6/ 4 Minutes 2 Legoland

GenesisRating, 5 stars1 month ago
We had a wonderful experience staying at this Airbnb. The host was incredibly accommodating and made sure we had everything we needed for a comfortable stay. The space was spotless, and it was clear that great care went into maintaining the property. From the little details to the overall comfort, everything exceeded our expectations. We would definitely recommend this host to anyone looking for a great place to stay!
Guest favourite
Flat in Woodstock
4.94 out of 5 average rating, 267 reviews

Jewel above the Pub with a view. Walk everywhere!

JonRating, 5 stars2 weeks ago
Perfect downtown Woodstock location! Just steps from excellent restaurants (Woodstock Pub, Silvia, Good Night), charming bars (Small Talk, Station), and countless boutique shops. The central spot also provides convenient access to surrounding areas like Phoenicia, Kingston, and Catskill. The dedicated parking spot, private entrance, straightforward check-in process, and responsive host communication made for a seamless stay. Would absolutely book again!
Guest favourite
Flat in Tannersville
4.9 out of 5 average rating, 116 reviews

D & D’s Place

AlaynaRating, 5 stars6 months ago
We had a great stay. It was a great quick weekend trip out of the city. This was our first time upstate and the location of Donna’s home was perfect. We had such a great time and would love to come back in the future.
Guest favourite
Flat in Hamden
4.95 out of 5 average rating, 102 reviews

Stylish, Renovated Private Catskills Apartment

JonathanRating, 5 stars2 months ago
Highly recommend this place. Dave was extremely responsive, informative, and friendly. There is plenty of room, and everything was very clean and tidy. The restaurant beneath the space is not only convenient, but the food was excellent as well. The surrounding area is very scenic, and is ideal for anyone looking for a peaceful getaway. Would definitely stay here again!
Guest favourite
Flat in Wallkill
4.89 out of 5 average rating, 393 reviews

Dream getaway apartment in the foot of Gunks Ridge

YehannysRating, 5 stars3 weeks ago
Nice stay! It was too short. I would have stayed longer. Very peaceful place! Thank you, Serg!!!
Top guest favourite
Flat in New Paltz
4.99 out of 5 average rating, 137 reviews

Escape To The Gunks! Very close to climbing routes

RimaRating, 5 stars4 days ago
Wonderful location close to New Paltz! super clean and Carmen was wonderful in answering any questions we had! highly recommend!
Guest favourite
Flat in Middletown
4.92 out of 5 average rating, 151 reviews

Just Around The Corner

SarahRating, 5 stars5 months ago
Had a great time! Loved the place and especially the surroundings, peaceful and beautiful!

Family-friendly apartment rentals

Superhost
Apartment in Vernon Township
4.79 out of 5 average rating, 122 reviews

Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

YanivRating, 5 stars1 month ago
Henry was helpful and super quick and responsive with all communication, which is key in making a comfortable stay. One thing that would be helpful for future guests is to include the precise location (or photos from the patio) of the condo. It faces the street, so for families with small children it may be a little louder compared to the condos on the mountain. Otherwise, we had a fantastic time, and would return for sure!
Top guest favourite
Apartment in Vernon Township
4.96 out of 5 average rating, 165 reviews

One bedroom condo at Mountain Creek Resort

MelissaRating, 5 stars1 month ago
We really enjoyed our stay! The condo was VERY clean, full stocked with all of the needed essentials and in a great location right by the ski slope. Both the bed and pull-out coach were SUPER comfortable. All instructions were super clear, and the recommendations were perfect. Thank you for letting us stay at your place, we love Mountain Creek!
Guest favourite
Apartment in Vernon Township
4.95 out of 5 average rating, 132 reviews

Sunsets at Mountain Creek! Walk to ski slopes!

MichelleRating, 5 stars2 months ago
Great place! Easy to check in and enjoyed the heated garage. It was super convenient to get to the room as well.
Guest favourite
Apartment in Vernon Township
4.94 out of 5 average rating, 831 reviews

Appalachian Lodge Top Floor w/views

ClaytonRating, 5 stars1 week ago
While i stayed here as a local for a quiet, low key, staycation to use the pool and hot tub as amenities, Paul's condo at the Appalachian is also perfect to utilize all that Mountain Creek has to offer, whether it be the water park in summer or the ski slopes in fall. The hotel itself is clean and quiet, and the condo is exactly how it is pictured-clean and cozy with a gas fireplace. I highly reccommend Paul's place as a launch pad during your trip to see what Sussex County and nearby Warwick NY have to offer
Superhost
Apartment in Vernon Township
4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

SaraRating, 5 stars5 months ago
We had a great time! The unit is an easy walk to Minerals, and the layout was perfect for our needs. Joann was a fantastic host and we can’t wait to stay again!
Guest favourite
Apartment in Vernon Township
4.92 out of 5 average rating, 316 reviews

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa

TrinityRating, 5 stars1 month ago
Beautiful place! It looks exactly like the pictures, very clean and the host was very helpful and responsive.
Top guest favourite
Apartment in Vernon Township
4.96 out of 5 average rating, 107 reviews

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

GregRating, 5 stars3 weeks ago
Massimo was so communicative, place was great, and the little extras provided -- snacks, beverages, and the set up for old time arcade games -- totally awesome! Thanks!
Top guest favourite
Apartment in Vernon Township
4.97 out of 5 average rating, 116 reviews

2 Bedroom + Parking Cozy Condo•Mountain Creek•

FrankRating, 5 stars1 month ago
The place was nice and clean as advertised. Host was very responsive. I would recommend this spot.

Quick stats about holiday rentals that are kid-friendly in Smallwood

  • Total rentals

    30 properties

  • Nightly prices starting at

    £68 before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore