Family-friendly vacation rentals in Smallwood

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.

4.98 out of 5 average rating, 117 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.

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.

4.84 out of 5 average rating, 244 reviews

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

4.92 out of 5 average rating, 113 reviews

chic renovated 'treehouse' with hot tub & fire pit

Escape to @boutiquerentals_' The Treehouse Bungalow–a renovated yet cozy 1930s Arts & Crafts cabin. Enjoy the hot tub, mountain views, fire pit & electric fireplaces. Located just 2 hrs from NYC in the Catskills (one of Travel+Leisure’s 50 Best Places), Smallwood is a destination in itself: walk along the lake, waterfall or hike the forest trails. Nearby is dining & shopping in Livingston Manor & Callicoon, holiday festivals, Bethel Woods, Kartrite Water Park & skiing+tubing at Holiday Mountain.

4.95 out of 5 average rating, 124 reviews

A charming treehouse, supported by sturdy posts, is nestled among tall trees. The wooden structure features a small balcony overlooked by bright green foliage, allowing sunlight to filter through. A path leads up to the entrance, surrounded by natural ground cover.

Treehouse in Hawley

Romantic Tiny Home Couples Cabin

Welcome to Treetop Getaways. We are a Luxury Treehouse vacation destination. These absolutely gorgeous little cabins have all of the amenities you could want from a comfortable stay, such as running water, showers, toilets, heat and ac...not to mention a nice cozy environment with beautiful Scenic views of the Wildlife Reserve behind us. With all of the lake activities, hiking, wineries, breweries amazing food and resorts/spas just minutes from your door, you will never run out of things to do!

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.

4.97 out of 5 average rating, 268 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 suite in Narrowsburg

The exterior features a charming porch with seating, surrounded by flowering plants. An American flag is displayed prominently. The building showcases a peaked roof and multiple windows, with a natural landscape of grass and trees in the background.

4.94 out of 5 average rating, 225 reviews

Modern Getaway in the Catskills

Our rental unit has a private entrance with kitchen, living & dining rooms and full bath on the first floor. 1 bedroom w/ Queen bed , AC and 1/2 bath on 2nd fl. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and Wi-Fi. A great getaway for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets, animals or children. All are welcome. Rainbow Friendly.

4.96 out of 5 average rating, 264 reviews

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 Bethel

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

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.

4.95 out of 5 average rating, 149 reviews

Cozy Scandi-Chic Renovated Cabin with Fireplace

Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat with a cozy fireplace & a fire pit in a woodland backyard. Located just 2 hours from NYC in the Catskills (one of Travel+Leisure’s 50 Best Places to Travel), Smallwood is a destination in itself: walk along the lake, waterfall or hike the forest trails. Nearby are Bethel Woods, Kartrite Waterpark, Holiday Mountain (skiing+tubing), Callicoon & Livingston Manor with dining & shopping.

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.

4.93 out of 5 average rating, 148 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.

4.94 out of 5 average rating, 160 reviews

A cozy outdoor seating area is surrounded by trees and fallen leaves. Four red chairs are positioned around a wooden table, with a fire pit in the center. String lights are draped overhead, creating a warm ambiance in the natural setting.

Home in Livingston Manor

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

The exterior of the barn cabin features a striking stone chimney and large windows, framed by a rich red exterior and a green metal roof. The surrounding lawn is lush and well-maintained, complementing the natural setting of trees in the background.

4.91 out of 5 average rating, 360 reviews

Cozy Post & Beam Barn Cabin w/Park near Bethel

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.

4.92 out of 5 average rating, 468 reviews

The cozy living area features a sofa and a teal armchair, surrounded by decorative lamps. A colorful striped rug adds warmth to the space. Natural light enters through the window, while vintage decor and string lights enhance the inviting ambiance.

Home in Narrowsburg

Cutest Little House in Narrowsburg

Relax in an idyllic wooded setting with 1000 feet of totally private river frontage, yet a 5 minute drive to Narrowsburg's restaurants and shops. If you like nature, privacy, history, vintage decor & design, this quaint 1950s cottage is for you. Hiking & campfires • Clawfoot tub • Front & back porches • Hummingbird & bunny watching • Den & WiFi • Peace & quiet • All included in your stay! Hundreds of 5-star reviews say it all. IG: #luxtonlake #tenmileriver #cutesthousenarrowsburg

Popular amenities for Smallwood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 144 reviews

A wooden dock extends over the calm water, featuring two lounge chairs facing the serene lake. Lush greenery borders the lake, with rolling hills visible in the background under a partly cloudy sky.

Cabin in Swan Lake

Lakefront Escape • Hot Tub • Kayaks •Free Firewood

4.96 out of 5 average rating, 372 reviews

Cabin in Wurtsboro

Summer Spa on a Cascading Brook - The Water House

4.84 out of 5 average rating, 129 reviews

An open-concept kitchen and living area features a large island with seating for eight, complemented by sleek black cabinetry. Bright light enters through multiple windows, illuminating the spacious layout that includes a comfortable seating arrangement and modern appliances.

Chalet in Monticello

Modern Chalet with Hot Tub and Lake Access

4.93 out of 5 average rating, 380 reviews

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, by camp caitlin

4.9 out of 5 average rating, 162 reviews

A red cabin with stone accents is surrounded by greenery, featuring a wooden porch with large windows. A gravel path leads to a patio area with a red umbrella, seating, and a grill in the fenced backyard, providing a welcoming outdoor space.

Cabin in Milford

Riverfront Cabin on the Delaware

5 out of 5 average rating, 202 reviews

The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.

Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

4.97 out of 5 average rating, 401 reviews

A quaint cabin sits nestled among tall trees, showcasing a sloped roof and red front door. Adjacent to the cabin is a wooden deck featuring a Finnish sauna and a long table, surrounded by a lush green landscape.

Cabin in Callicoon

Chic Cabin on Callicoon Creek

4.99 out of 5 average rating, 163 reviews

The cabin is positioned in a wooded area, featuring a dark exterior and a sloped roof. A spacious patio area is visible, equipped with seating and a fire pit. A hot tub is placed nearby, illuminated by soft lighting along the pathways.

Cabin in Ellenville

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 243 reviews

The exterior of a freshly renovated schoolhouse features a welcoming porch with wooden railings and a gabled roof. A central front door is flanked by decorative lanterns and small green shrubs. Two dark, framed windows provide a touch of elegance on either side.

Cottage in Narrowsburg

Luxury Historic School House Cottage

4.97 out of 5 average rating, 108 reviews

A serene view of a MidCentury bungalow, framed by lush greenery. The house, featuring large windows, is illuminated from within, reflecting a warm glow. A clear evening sky is visible, alongside the presence of the moon.

Home in Monticello

Cozy Catskills Lakeside

4.87 out of 5 average rating, 285 reviews

A rustic cabin is positioned among lush trees, featuring a cozy front porch with wooden steps. The exterior showcases natural tones, complemented by decorative wildlife silhouettes. An expansive grassy area surrounds the cabin, inviting outdoor activities.

Cabin in Ferndale

Catskill mountain getaway

4.96 out of 5 average rating, 417 reviews

The interior of the yurt is illuminated by natural light from the skylight dome, highlighting the wood framework. A queen bed with a canopy is the focal point, surrounded by a dining table, chairs, and a storage dresser. Decorative elements add a sense of warmth.

Yurt in South Sterling

Yurt at the farm!

4.82 out of 5 average rating, 152 reviews

The tiny house exterior is illuminated by string lights, creating a warm atmosphere at night. A set of wooden stairs leads to the front door, framed by two inviting chairs on the porch. Surrounding trees provide a natural backdrop, enhancing the secluded feel.

Tiny home in Rock Hill

Trails Head Tiny House

4.99 out of 5 average rating, 327 reviews

The great room features a rustic stone fireplace as its focal point, surrounded by wooden beams and large windows allowing natural light. Two couches of varying styles are arranged around a wooden coffee table, providing a cozy setting for gatherings.

Home in Callicoon

Paradise in the Catskills

5 out of 5 average rating, 187 reviews

A charming 1930's cottage is set against a backdrop of vibrant autumn foliage. The structure is surrounded by a spacious lawn, leading to glimpses of the river nearby. Brightly colored leaves adorn the trees, contributing to the serene and natural atmosphere.

Cottage in Narrowsburg

Upper Delaware River cottage

4.9 out of 5 average rating, 237 reviews

The living area features large windows that allow natural light to fill the space, complemented by a wood-burning stove. A cozy gray sofa and rustic chairs surround a circular wooden coffee table, while a textured area rug adds warmth to the hardwood floor.

Home in Monticello

Dancing Feather: Cozy Lake-Front A-Frame Chalet

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 284 reviews

Cabin in Hamlin

Mid-century A-frame nestled amongst the trees

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.

4.83 out of 5 average rating, 216 reviews

Stunning Mountain Cabin w/ Pool & Hot Tub

Cabin in Livingston Manor

An aerial view captures a charming cabin surrounded by lush trees, with a vibrant sunset sky in shades of pink and purple. The spacious yard is highlighted by a hot tub, outdoor seating area, and fire pit, inviting relaxation and gatherings in nature.

4.97 out of 5 average rating, 326 reviews

Experience The Zen House

Home in Lackawaxen Township

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.

5 out of 5 average rating, 119 reviews

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

4.98 out of 5 average rating, 128 reviews

Cottage in Eldred

Bella Cottage w/Cozy Fireplace & BBQ, Fall Getaway

4.94 out of 5 average rating, 220 reviews

Home in Narrowsburg

Modern House with Hot-Tub and Fireplace

4.97 out of 5 average rating, 146 reviews

A dog sits upright on a wooden chair at a kitchen countertop. The space features warm wooden accents and a cozy atmosphere, with a sofa and dining area visible in the background. Natural light filters through a nearby window, highlighting the dog's glossy coat.

Home in Downsville

Trout fishing on the Delaware