
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 Built in pool/over flow jacuzzi in May
We had an amazing stay at Jeffery’s house. From booking to checkout super responsive and proactively gave us tips for areas to explore and restaurants outside. Lovely backyard trail. The house gets well heated. Peaceful stay. 6/5

Perfect Family Winter Retreat•Close to Ski•Firepit
We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!

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 :)

Skiing and Breweries! Mountain and river views!
My adult daughters and I came up for Presidents Day weekend. There was a winter storm and very cold and windy- even closed the mountain where we were going to cross country ski at. We spent a lot of time in the house. It is clean and very warm and very nicely furnished. The kitchen has everything needed with quality cookware. Beds were comfortable with nice linens and plenty of clean towels. Overall a very nice place to stay.

Entire lake house to yourself. Great for groups
Despite booking my stay with three other friends for my birthday during February, it was the absolute best decision. Everything was as described, lot of great in-home amenities including games (i.e. ping pong, pool, tons of table-top entertainment.) Scott was absolutely one of the best hosts I have coordinated and communicated with. He would check-in to ensure we had what we needed and when there was a heavy snowfall the evening prior to our departure date- he immediately checked in and had the walkway and driveway cleared of snow. Lot of great, beautiful hikes in the snowfall and do hope to have the opportunity to return during the warmer season. Thank you, again, for the wonderful accommodations and for being such a proactive and communicative host!

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.

Heated Saltwater Pool/Hot Tub/Kid Friendly!
This is the first time a listing with "kid friendly" has truly fit the description! We have two littles and Neesha's home did not disappoint with safety guards, toys, books, games, crib and small beds. Everything was available down to the highchair, noise machines and monitors. Anyone who travels with kids can appreciate having all of these necessities available and ready to use. It's a whole suitcase less for the trip! The home itself is beautiful, pristine, spacious yet still very cozy. It felt like a quiet family retreat with our own jungle gym in the backyard and a fire pit for smores. The town of Kingston was not far away - we rode the Polar Express. And for more adventures, Woodstock is super close and has great shops and restaurants too. But we didn't have much desire to leave Neesha's home. We loved the chef's kitchen (fully equipped) and had many family meals in the dinning room. Our host was very responsive and accommodating. We will definitely be back.
Family-friendly apartment rentals

Mountain View Apartment
We have stayed here more times that I can count. Bob and Jacki's place is a great get-away. Comfortable, cozy and so clean and well stocked for a longer stay. If you see how many times I left a glowing review you will see I mean it since we keep coming back. It is our go to spot when staying in the Catskills. Thank you as always, Bob and Jacki!!

Location! Super clean apt. 8 min walk to Hunter!
We had an awesome experience! I would recommend staying here! The place was clean and looked just like the photos. It was super comfortable and had a nice ski cabin feel. John was super communicative and helpful throughout our stay.

Homey Haven:Inviting Airbnb Suite with kitchen
Nichole is a fantastic host and this place was just what we needed and just as advertized. Nichole was quick to respond to questions and the entire atmosphere is very cozy! Very close to all the great New Paltz restaurants!

Jewel above the Pub with a view. Walk everywhere!
This place is truly a jewel!! Everything was easy and convenient. We were able to walk everywhere. This place was roomy, very clean and well stocked. We can't wait to go back:)

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.

Charming Efficiency
This stay was clean and cozy! We stayed here for one night during our trip across the country for the holidays and were so happy to have this lovely space to rest in with our pup. Laurie left several treats for us and generally made the space welcoming. We got some good Chinese food and enjoyed a peaceful, snowy evening. We will definitely stay here again if we follow the same route 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!

Hot Tub Bliss 5mi to Kingston on 3 acres
Kim’s place is clean and has almost averything we need. There’s even free snacks when we arrived. We feel that we are home just far away from our own home. Hot tub did not fail us. It was so relaxing even with snow around us and rain pouring. We enjoyed our stay.
Family-friendly apartment rentals

One bedroom condo at Mountain Creek Resort
It was a wonderful stay at Kritof's condo. He gave us a thorough check in instructions which made check in very easy. He even let us know the place was available earlier for check in which was nice. The condo was nice and clean with everything stocked and available. We had a great time skiing at Mountain Creek Ski resort. Thank you for a comfortable, relaxing stay!!

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
Nice place for family skiing trip, walkable to the ski trails, parking and the hot tub pool is an extra bonus.

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!

Ski on/ Ski off Stylish Condo Hunter Mountain
This was a great spot to stay especially if you plan on skiing Hunter Mountain. Super short walk to the trail. Very quiet area and some great resturants and breweries. We will be back!

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa
We had a great stay. Not too far from the ski lift. Very peaceful and quiet. The condo was very clean and comfortable. LPG was very accommodating with our special request which was much appreciated.

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
I highly recommend this unit. It is exactly like the listing/photos, newly remodeled, and fantastic big windows with a ton of natural light. Massimo was super responsive, especially the day of my check-in when my car battery died in the parking garage! He was very helpful. I travelled with my 9 and 2 year old and it was very comfortable for the kids. Perfect rental for ski in/out on Mountain Creek.

NYC Escape 1 hr away
Enjoyed are stay. So convenient to be right next to mountain creek ski lodge.
Quick stats about holiday rentals that are kid-friendly in Smallwood
Total rentals
20 properties
Nightly prices starting at
£85 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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