
Kid-friendly holiday rentals in Smallwood
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Top-rated family-friendly rentals in Smallwood
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Popular amenities for Smallwood family-friendly rentals
Kid-friendly house rentals

Farm House with Built in pool/jacuzzi open in May
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!

Grandma's Cottage 2BR+Den
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!

Cozy Outdoor Firepit-Fireplace-Close to Skiing
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 :)

Dog-friendly Winter Wonderland Retreat
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.

Hiking and Breweries! Mountain and river views!
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!

Winter Home near Legoland, West Point & Outlet
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!

NEW! Fun and relaxing home for friends and family!
Lovely home. The kids enjoyed the game room. We had a great time!

Sweeping mountain views in Woodstock, NY
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

Log Cabin Apartment Great for Outdoor Enthusiasts
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.

Historic Horse Barn Sleeps 6/ 4 Minutes 2 Legoland
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!

Jewel above the Pub with a view. Walk everywhere!
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!

D & D’s Place
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.

Stylish, Renovated Private Catskills Apartment
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!

Dream getaway apartment in the foot of Gunks Ridge
Nice stay! It was too short. I would have stayed longer. Very peaceful place! Thank you, Serg!!!

Escape To The Gunks! Very close to climbing routes
Wonderful location close to New Paltz! super clean and Carmen was wonderful in answering any questions we had! highly recommend!

Just Around The Corner
Had a great time! Loved the place and especially the surroundings, peaceful and beautiful!
Family-friendly apartment rentals

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

One bedroom condo at Mountain Creek Resort
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!

Sunsets at Mountain Creek! Walk to ski slopes!
Great place! Easy to check in and enjoyed the heated garage. It was super convenient to get to the room as well.

Appalachian Lodge Top Floor w/views
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

200 yds Minerals - great for hotel weddings
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!

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa
Beautiful place! It looks exactly like the pictures, very clean and the host was very helpful and responsive.

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
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!

2 Bedroom + Parking Cozy Condo•Mountain Creek•
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
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- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Kalahari Resorts
- Elk Mountain Ski Resort
- Montage Mountain Resorts
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Bushkill Falls
- The Kartrite Resort & Indoor Waterpark
- Aquatopia Indoor Waterpark
- Resorts World Catskills
- Promised Land State Park
- Delaware Water Gap National Recreation Area
- Opus 40
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Ringwood State Park
- Camelback Snowtubing
- Sunset Hill Shooting Range
- Thaddeus Hait Farm
- Mount Peter Ski Area
- Sterling Forest State Park
- Wawayanda State Park
- Tobyhanna State Park