Family-friendly holiday 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.

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Top Guest favourite
A vibrant red cabin is surrounded by a grassy area, featuring a circle of white Adirondack chairs positioned around a fire pit. A wooden deck with railing extends from the cabin, while the backdrop includes trees and a clear blue sky.
Cabin in Smallwood
4.98 out of 5 average rating, 125 reviews

Cozy Lake Cabin with fireplace - Pets Welcome

Spot deer daily at this cozy nature lovers getaway. This Smallwood cabin has a fun colorful retro vibe and can sleep up to 4 people. Pets are welcome. Located just minutes walk to mountain lake, 10 mins to Bethel Woods Center for the Arts, 20 mins to Narrowsburg, Barryville, Livingston Manor and many other cute towns. Large fenced in backyard with woodsy views and outdoor fire pit, large deck with bbq, fully equipped kitchen. Cozy indoor fireplace, smart TV with netflix, workspace, fast wifi.

Guest favourite
Cabin in Smallwood
4.92 out of 5 average rating, 125 reviews

renovated–hot tub–lake access+pedal boat–cozy+chic

Escape to @boutiquerentals_' The Treehouse Bungalow – a cozy renovated 1930s Arts & Crafts cabin with hot tub, fire pit, mountain/treehouse views, Scandi-chic decor, picnic table & BBQ. Just 2 hours from NYC in the Catskills with seasonal lake access, pedal boat & paddle boards, waterfall, forest trails & proximity to Delaware River tubing/rafting. Visit antique shops, Bethel Woods Center for the Arts, Kartrite Waterpark, breweries & charming towns like Callicoon, Narrowsburg & Livingston Manor.

Guest favourite
The cabin is softly illuminated by outdoor string lights at dusk, creating a welcoming atmosphere. A stone pathway leads to a fire pit surrounded by four Adirondack chairs, while the cabin's deck features inviting seating. Lush trees provide a natural backdrop.
Cabin in Smallwood
4.94 out of 5 average rating, 170 reviews

Fireplace—Chic & Renovated—Fire Pit—Canoe & SUPs

'The Original Bungalow,' part of the @boutiquerentals_' collection, is a Scandi-chic renovated bungalow surrounded by stunning trees. Located only 2 hours from NYC, Smallwood is a destination in itself: walk along the lake or waterfall, or take the canoe or SUPs for a paddle (seasonal). Nearby are Bethel Woods Center for the Arts, breweries, Livingston Manor & cute Delaware River towns with dining+shopping. In the evening, unwind by the fire pit or curl up by the fireplace with a book or movie.

Top Guest favourite
A stone path leads to a tranquil outdoor area surrounded by trees, featuring several seating options including adirondack chairs. A flowing stream can be seen in the background, providing a serene backdrop to this private space.
Cabin in Smallwood
4.98 out of 5 average rating, 280 reviews

Beautiful & Secluded Streamside Catskills Cabin

Private & secluded Smallwood cabin sleeps 6. Central A/C. Park & Hear the stream flowing when you pull up. Large great room with fireplace & windows overlooking backyard stream. 1 master bedroom, 1 separate guest room, 1 open sleep loft (2 twin beds) Enjoy evenings on the deck, or by the outdoor fire pit listening to the stream that leads to a small waterfall. Enjoy the swim pit right in your backyard! Outdoor Shower! Close to Bethel Woods, hiking & White Lake dining & Toronto Reservoir

Guest favourite
A hot tub is surrounded by lush greenery and illuminated by string lights, creating a serene outdoor setting. A stone path leads to the hot tub, with red chairs visible nearby, all nestled within a wooded area.
Cottage in Mongaup Valley
4.96 out of 5 average rating, 277 reviews

Hot Tub, Playground, 3 Acres, and Much More!

Relax with the whole family at this peaceful cottage in the trees 5 minutes from Bethel Woods - check out their upcoming events! Recently renovated cottage with hot tub, an electric fireplace, washer and dryer, dishwasher, and smart TVs. Family-friendly features include a baby gate, potty training seat, high chair, toddler-safe bunk beds, and toys Outdoor features include 2 fire pits, trampoline, jungle gym, basketball hoop, walking path, stream w/ waterfall, and 3 acres of woods to explore

Guest favourite
The A-frame cabin is surrounded by trees and set on a grassy area. A fire pit with seating is situated in front, with smoke rising gently in the evening light. The cabin's large windows reveal a welcoming interior, illuminated by natural light.
Home in Jeffersonville
4.99 out of 5 average rating, 244 reviews

BirchRidge A-Frame: Sauna/Firepit/King Bed/7 Acres

Nestled in the Catskills Forest, less than 2 hrs from NYC, you'll find Birch Ridge A-frame! This gorgeous 2-bedroom cabin is set on 7 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that creates a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

Top Guest favourite
A warm living area is highlighted by a wood-burning stove at its center, surrounded by a cowhide rug. Light-colored armchairs are positioned alongside a wooden coffee table. Natural light enters through multi-pane windows, complemented by a guitar and decorative plants against the walls.
Cabin in Monticello
4.94 out of 5 average rating, 159 reviews

Cozy Catskills Cabin

Give yourself time away from the city and closer to nature. Go for a hike, a dip in the lake, or simply relax, take your shoes off and put a good record on. Casa Smallwood got its name from the hamlet of Smallwood, a quaint community of cabins from the 30's and 40's, nestled less than 2 hours from NYC. We're only 7 minutes away from BethelWoods Arts Center, the original site of the 1969 Woodstock Festival. Come stay with us and surround yourself with beautiful trees, lakes, love and peace.

Guest favourite
Cabin in Mongaup Valley
4.91 out of 5 average rating, 368 reviews

Cozy Barn Cabin near Ski Mountain & Bethel Woods

1200 sq. ft Post & Beam 2 story Barn Cabin set on 18+ acres of property w/1250 ft. of rd frontage leading to this gem. Amish wood furniture and a wood burning stove. Open loft concept on 2nd floor offers 1 king bed, a trundle bed with 2 twins (sleeps 4), 1/2 bath & closet space. Downstairs offers kitchen, dining room, living room and full bath. Private park on property w/hammock, volleyball & basketball court, swing set, slide & playhouse, yard games (in house & shed) barbecue & firepit.

Guest favourite
A spacious living area features a sectional sofa adorned with patterned cushions. Two wooden side tables sit on a plush area rug, while natural light enters through a window framed by light curtains. A rustic paddle and framed artwork decorate the walls.
Home in Roscoe
4.94 out of 5 average rating, 119 reviews

River House at Trout Town Farms

Fully furnished River House with private access to the famous Beaverkill River Lower Mountain Pool. You can walk through a real working farm as well as taste the seasonal harvest when available. Here you can take a farm tour and visit with our resident animals, including alpacas, Nigerian dwarf goats, rabbits, and chickens. Whether it's fishing, relaxing by the fire, or sitting on the patio listening to the river, this farmhouse offers a peaceful retreat for the whole family to stay.

Guest favourite
The cabin’s exterior is framed by lush greenery and flowering shrubs. A stone pathway leads to the front door, which is flanked by a porch. The wood siding and large windows create a welcoming facade, surrounded by trees and a well-kept lawn.
Cabin in Bethel
4.96 out of 5 average rating, 100 reviews

Cozy Catskills Lake Region Cabin in Smallwood

Welcome to this charming Catskills cabin in the hamlet of Smallwood, less than 2 hours from NYC! Relax and unwind surrounded by nature while still centrally located to many attractions. 10 minutes from Bethel Woods. Less than 10 minutes from White Lake with waterfront dining, boat and Jet Ski rentals. 20 minutes from Resorts World Casino, Kartrite indoor water park, Holiday Mountain Ski Resort. River tubing, Legoland, state parks, hiking, swimming, breweries and more!

Top Guest favourite
An outdoor area showcases multiple seating options, including six Adirondack chairs arranged around a fire pit. The backdrop is formed by a modern container home surrounded by colorful autumn foliage, complemented by a deck and outdoor dining setup, enhancing the serene atmosphere.
Shipping container in Smallwood
4.98 out of 5 average rating, 113 reviews

Unique Container Home w/ Hot Tub, Fire Pit & More!

Coined the "Eikonic Box" for its iconic look- you'll be amazed by the flying boxes with unique views of the gorgeous forest views. Escape the ordinary and immerse yourself in the modern comfort of this stylish 3-BR retreat. Designed with sustainability and creativity in mind, our container home offers a one-of-a-kind lodging experience for those seeking a blend of innovation & relaxation. Book today and experience the charm of container living! Message me for Q's

Superhost
A serene lake house is nestled among tall trees beside a calm body of water. A grassy area extends from the house towards the lakeside, with outdoor seating arranged on the lawn. The home features large windows, inviting natural light into the living space.
Home in Swan Lake
4.88 out of 5 average rating, 486 reviews

In the clouds your cozy- lake house

Cozy lake house in Catskill,only 2 hrs away from NYC.The property has 2 Bedroom 1-1/2 baths & sleeps 4-6 people. Guest can enjoy kayaking fishing in property.The property is close proximity 2 downtown Jeffersonville & Bethel-Woods Center for Arts (Historic Site of the 1969 Woodstock Music & Art Fair).Nearby attractions ~ Villa Roma Resorts,Resort World Casino, Kartrite Resort & Water park & Holiday Mountain Ski resort.Visit local farms and Catskill brewery

Popular amenities for Smallwood family-friendly rentals

When is the best time to visit Smallwood?

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Avg. price$316 NZD$322 NZD$302 NZD$280 NZD$322 NZD$299 NZD$349 NZD$368 NZD$322 NZD$317 NZD$316 NZD$329 NZD
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Quick stats about holiday rentals that are family-friendly in Smallwood

  • Total holiday rentals

    Explore 80 holiday rentals in Smallwood

  • Nightly prices starting at

    Smallwood holiday rentals start at $187 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,740 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Smallwood holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Smallwood rentals

  • 4.8 Average rating

    Smallwood stays are highly rated by guests—averaging 4.8 out of 5!