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Family-friendly vacation rentals in Smallwood

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Smallwood

  • Total vacation rentals

    Explore 90 vacation rentals in Smallwood

  • Nightly prices starting at

    Smallwood vacation rentals start at ﺩ.ﺇ 404 per night before taxes and fees

  • Verified guest reviews

    Over 5,180 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Smallwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Smallwood rentals

  • 4.9 Average rating

    Smallwood stays are highly rated by guests—averaging 4.9 out of 5!

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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Guest favorite
The open living area features a comfortable seating arrangement with a neutral-colored couch and a patterned area rug. A TV stand with a television is situated against one wall. The loft and bedroom are visible in the background, adding a sense of spaciousness to the layout.
Cabin in Smallwood

Comfortable Catskill Cabin minutes to Bethel Woods

Comfortable, private home very close to Bethel Woods on a quiet dead-end street in a desirable mountain lake community. Two bedrooms & a loft, WiFi, heat/AC, deck with BBQ grill, picnic table & fire pit. In the heart of the Sullivan County Catskills centrally located to the many attractions this vacation recreation area has to offer: site seeing, concerts, hiking, camping, skiing, breweries/wineries, boating, parks, antiquing, casinos, wedding venues, museums, Delaware River, hunting/fishing etc

FamilyKitchenGrill

4.84 out of 5 average rating, 264 reviews
Guest favorite
Cabin in Smallwood

Canoe—Lake Access—Fireplace+Pit—BBQ—Fall Foliage

Enjoy nature at @boutiquerentals_' The Original Bungalow with décor inspired by our native Sweden. Take a stroll to a nearby lake, waterfall, hiking trails, or use our canoe/SUPs to explore the waters. Visit Bethel Woods Center for the Arts & Woodstock site, an apple orchard, fall festival, art museum, alpaca farm, brewery, or charming towns like Jeffersonville & Narrowsburg with excellent shopping+dining. In the evening, fire up the BBQ & unwind on the deck, by the fire pit or cozy fireplace.

Indoor spacesKitchenGrill

4.94 out of 5 average rating, 188 reviews
Top guest favorite
Cabin in Smallwood

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

FamilyKitchenView

4.97 out of 5 average rating, 303 reviews
Top guest favorite
A screened-in deck is furnished with a comfortable sitting area featuring a wooden coffee table and plush seating. Two hammocks are suspended from the ceiling, with a ceiling fan providing a gentle breeze. Green walls and decorative plants add a touch of nature to the space.
Cabin in Smallwood

Cozy cabin near Bethel Woods/ Toronto Reservoir

Birmwood is country living at it's best, less than 2 hrs. From NYC! Rustic interior with wood stove and over an acre of woods to enjoy, you can get lost in the peacefulness of Smallwood right in your own backyard. 2 bedrooms with queen size beds, this cabin sleeps 4. Enjoy the private deck, fire pits, hammock, grill & wildlife. There is no access to the nearest Lake or beach but Lake Superior, Toronto Res, Swinging Bridge, are all close. Bethel Woods-original site of WOODSTOCK is 3 miles away!

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 186 reviews
Top guest favorite
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

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

FamilyIndoor spacesAir conditioning

4.97 out of 5 average rating, 305 reviews
Top guest favorite
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

Luxury Container | Hot Tub | Rooftop Tub | Pizza

Escape to a one-of-a-kind luxury container home nestled in the Catskills, featuring a year-round hot tub, rooftop soaking tub, outdoor kitchen, pizza oven, and peaceful forest views. Escape the ordinary and immerse yourself in this stylish 3-BR container 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 container living! Message me for Q's

KitchenFamilyLayout

4.99 out of 5 average rating, 136 reviews
Guest favorite
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

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.

KitchenFamilyCleanliness

4.94 out of 5 average rating, 171 reviews
Top guest favorite
A wooden deck is softly illuminated by candlelight, creating a serene atmosphere. A staircase leads to a wooden hot tub surrounded by lush foliage. The evening sky, deepening into twilight, adds to the tranquil ambiance of the outdoor space.
Cabin in Monticello

Blue House | Cedar tub•BBQ•fire pit•stargazing

Nestled in the Catskills Mountain region, between the Delaware and Hudson Rivers in the community of Monticello. Insta @bluehouseofcatskills offers a year-round retreat away from the hustle and bustle of the city. Spectacular stary nights, wildlife in the backyard, hiking trails, swimming and skiing all a short drive away. The Blue House is a wonderful getaway for all to enjoy. Modern and contemporary design the Blue House offers comfortable king and queen bedrooms and a spacious living area.

Indoor spacesFamilyNearby

4.93 out of 5 average rating, 176 reviews
Top guest favorite
Two kayaks, colored yellow and orange, rest on the grassy shore of a serene lake. A small dock extends into the calm water, reflecting the colors of a sunset sky. Trees line the horizon, completing the tranquil lakeside setting.
Cottage in Livingston Manor

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

KitchenFamilyGetting around

5.0 out of 5 average rating, 110 reviews
Top guest favorite
A two-bedroom log cabin is presented with a dark blue exterior and a welcoming front entrance. Surrounding greenery includes a variety of plants and trees, complemented by a large tree stump nearby. The cabin features a stone foundation and is designed for leisure and comfort.
Cabin in Smallwood

Cozy Lakeside Cabin by Bethel Woods & Casino

This is a 1000 square-foot, two-bedroom log cabin with a sleeping loft. I prefer groups of 4 or less but may accommodate more for an extra fee. Enjoy the new fire pit out back on a cold night. Plenty of board games are available and my kitchen is stocked with spices and cookware. ***5/28/26: Pac-Man arcade pictured needs repair, currently has a faulty display. Walk Mountain Lake, which sits across the street and spans exactly 2 miles around. Or just get some R&R - my beds are so comfy!

Indoor spacesFamilyCleanliness

5.0 out of 5 average rating, 129 reviews
Top guest favorite
Cabin in Mongaup Valley

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.

KitchenIndoor spacesCleanliness

4.91 out of 5 average rating, 391 reviews
Top guest favorite
Home in Swan Lake

Game Room, 20 Acres, Oversized Rooms

The Modern Retro Ranch is a sprawling 1 story house - funky and modern with a touch of 60s style. Outdoor hot tub. 20 private acres with no neighbors in sight. The living room, kitchen and dining rooms are oversized with multiple gathering areas. Grill, large firepit, linens, towels included. Close to Bethel Woods and many local attractions *see below. Fast Wifi. Enhance your trip with our recommendations: private chef, masseuse, yoga. More amenities are in the works for the near future

KitchenIndoor spacesLocation

4.92 out of 5 average rating, 218 reviews

Popular amenities for Smallwood family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
Home in Narrowsburg

3BR/2BA • Fireplace & Hot Tub Near Bethel Woods

Indoor spacesKitchenCleanliness

4.93 out of 5 average rating, 247 reviews
Superhost
Home in Swan Lake

9BR Log Cabin Home w/ Hot Tub & Swimmable Pond

Indoor spacesKitchenHospitality

4.86 out of 5 average rating, 117 reviews
Top guest favorite
Home in Swan Lake

Peaceful Escape • Hot Tub • Fire Pit • Views

FamilyIndoor spacesNearby

4.83 out of 5 average rating, 128 reviews
Top guest favorite
A unique octagonal structure features a raised deck surrounded by a wooden railing. Large windows provide views of the surrounding trees and landscape. A staircase leads to the entrance, emphasizing the elevated position of the house in a serene woodland setting.
Cabin in Beach Lake

the tree house, Wood Fired Hot Tub/Barrel Sauna

FamilyKitchenGetting around

4.93 out of 5 average rating, 422 reviews
Superhost
A spacious jacuzzi is set on a wooden deck, surrounded by nature. The water's vibrant blue color reflects the sunlight. Nearby, comfortable black wicker seating can be seen, perfect for relaxing while enjoying the views of the trees.
Cottage in Monticello

Lovely Cottage w/ Jacuzzi+Access to Nearby Lakes!

KitchenFamilyPets

4.91 out of 5 average rating, 174 reviews
Top guest favorite
A spacious golf simulator room features a large projection screen displaying a scenic golf course. A putting green is positioned in front, and golf clubs are displayed in the corner. Soft lighting enhances the ambiance, providing a comfortable setting for practice or entertainment.
Home in Lackawaxen

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

KitchenFamilyCleanliness

4.99 out of 5 average rating, 145 reviews
Top guest favorite
A serene cabin is nestled among trees, overlooking a private pond. The exterior features a mix of corrugated metal and wood, blending harmoniously with the natural surroundings. A spacious outdoor area includes a fire pit and seating, offering a tranquil retreat.
Cabin in Mountain Dale

Private lake cabin w/hot tub, views and fruit

Indoor spacesFamilyLocation

4.96 out of 5 average rating, 208 reviews
Top guest favorite
Cabin in Swan Lake

Lakefront Escape • Hot Tub • Kayaks •Free Firewood

KitchenIndoor spacesLocation

4.94 out of 5 average rating, 212 reviews

Family- and pet-friendly home rentals

Superhost
A rustic living area features a stone fireplace with a warm fire, surrounded by logs and rich fabric curtains. A plush couch is covered with a red plaid throw, and a television is mounted above the fireplace. Soft lighting and a chandelier provide a cozy ambiance.
Home in Bethel

1913 Love Shack Cheap week2miles from Bethelwoods

FamilyIndoor spacesGrill

4.93 out of 5 average rating, 176 reviews
Top guest favorite
Home in Liberty

Creekside Retreat•Fire Pit•Game Room•Dog Friendly

Indoor spacesKitchenNearby

4.99 out of 5 average rating, 137 reviews
Superhost
An indoor heated pool area features large windows allowing natural light to fill the space. Surrounding the pool are loungers, a colorful floating swan, and a bright orange inflatable, creating a cheerful atmosphere. Wood paneling and a beamed ceiling complete the inviting setting.
Home in North Branch

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

KitchenIndoor spacesSleep quality

4.89 out of 5 average rating, 181 reviews
Superhost
Two black Adirondack chairs are placed beside a small round table on a wooden deck, overlooking Kauneonga Lake. The sunset casts soft hues across the water, while the shoreline and trees are silhouetted against a colorful sky.
Apartment in Kauneonga Lake

Lakeside Studio on White Lake

KitchenIndoor spacesValue

4.85 out of 5 average rating, 215 reviews
Top guest favorite
Cottage in Kenoza Lake

The Schoolhouse at Kenoza Lake

KitchenFamilyLaundry

4.95 out of 5 average rating, 174 reviews
Top guest favorite
Home in Damascus

Delaware River retreat

Indoor spacesFamilyComfort

4.94 out of 5 average rating, 206 reviews
Top guest favorite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor

Peaceful creekside retreat near Livingston Manor

FamilyIndoor spacesWalkability

4.96 out of 5 average rating, 432 reviews
Top guest favorite
Cabin in Yulan

Enchanting River A-Frame|Fire Pit| Magical Forest

FamilyIndoor spacesCheckout

4.98 out of 5 average rating, 239 reviews

Family-friendly home rentals with a pool

Top guest favorite
The image features a clear, inviting pool in the foreground, with the country home visible in the background. Surrounded by lush greenery, the house has a deck and large windows, blending harmoniously with the serene wooded landscape.
Cottage in Eldred

Bella Cottage w/Pool, BBQ - Catskill Getaway

FamilyKitchenNearby

4.98 out of 5 average rating, 139 reviews
Superhost
An inviting living space showcases expansive floor-to-ceiling windows, allowing natural light to illuminate the room. A cozy sofa is complemented by stylish chairs, while a large area rug unifies the seating arrangement. Dining space is visible in the background, enhancing the open floor plan.
Cabin in Swan Lake

Modern Catskills Home w/ Pool, Hot Tub & 10 Acres

KitchenFamilyOutdoor spaces

4.81 out of 5 average rating, 253 reviews
Guest favorite
A bright living area showcases wooden beams and a cozy seating arrangement. A light gray sofa is paired with an armchair, while a colorful storage unit holds records. The space is highlighted by a patterned rug and a dining area visible in the background.
Cabin in Eldred

Secluded Cool Summer Cabin with mini pool

FamilyKitchenGrill

4.94 out of 5 average rating, 219 reviews
Guest favorite
An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.
Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

FamilyIndoor spacesNearby

4.91 out of 5 average rating, 126 reviews
Top guest favorite
An inviting hot tub is positioned on a wooden deck, overlooking a spacious backyard and the tastefully designed home. Soft lighting enhances the outdoor setting as sunset hues paint the sky, creating a serene atmosphere perfect for relaxation.
Cabin in Livingston Manor

Experience The Zen House

FamilyKitchenOutdoor spaces

4.97 out of 5 average rating, 359 reviews
Guest favorite
Home in Lakeville

Heated pool sauna and jacuzzi Lake Wallenpaupack

FamilyIndoor spacesCleanliness

4.87 out of 5 average rating, 180 reviews
Guest favorite
A chalet is nestled among tall trees, with a quaint exterior featuring dark and light wood accents. Two red Adirondack chairs are positioned around a stone fire pit, providing a cozy gathering spot. A spacious deck extends from the home, blending into the natural surroundings.
Chalet in Lackawaxen

Secret Getaway Nestled in a Woodland Setting

KitchenIndoor spacesParks

4.92 out of 5 average rating, 407 reviews
Top guest favorite
Tiny home in Narrowsburg

Dog friendly, heated pool & Hot Tub w/ fenced yard

KitchenFamilyRiver

4.99 out of 5 average rating, 105 reviews

When is the best time to visit Smallwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 738ﺩ.ﺇ 661ﺩ.ﺇ 591ﺩ.ﺇ 650ﺩ.ﺇ 709ﺩ.ﺇ 690ﺩ.ﺇ 757ﺩ.ﺇ 797ﺩ.ﺇ 698ﺩ.ﺇ 687ﺩ.ﺇ 683ﺩ.ﺇ 712
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