
Family-friendly vacation 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.

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.

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

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!

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

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

Fireplace—Renovated—Near Skiing & Tubing—Chic+Cozy
Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat with a cozy fireplace & fire pit in a woodland backyard. Located just 2 hours 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 are Holiday Mountain (skiing+tubing), Kartrite Waterpark, Bethel Woods + dining & shopping in Callicoon, Livingston Manor & Narrowsburg.

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.

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.

renovated–hot tub–near skiing+tubing–cozy & chic
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 & Narrowsburg, skiing+tubing at Holiday Mountain, Bethel Woods & Kartrite Waterpark.

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.

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

Hot Tub, Fire Pit, Games, PizzaOven, Holiday Decor
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 your stay today and experience the charm of container living! Message me for Q's!
Popular amenities for Smallwood family-friendly rentals
Family-friendly home rentals with a hot tub

The Water House - Winter Spa on a Cascading Brook

Modern Chalet with Hot Tub and Lake Access

the tree house, by camp caitlin

Chic Cabin on Callicoon Creek

Lovely Cottage w/ Jacuzzi+Woodstove!

Guesthouse On old 1879 Farm. Hot tub, hiking.

Charming cottage with Hot Tub -PET FRIENDLY

Private lake cabin w/hot tub, views and fruit
Family- and pet-friendly home rentals

R & R On The Knoll

Delaware River Cottage

Yurt at the farm!

Trails Head Tiny House

Upper Delaware River cottage

Lakeside Studio on White Lake

The Fern Hill Lodge: Secluded Serenity on 20 Acres

Dancing Feather: Cozy Lake-Front A-Frame Chalet
Family-friendly home rentals with a pool

Mid-century A-frame nestled amongst the trees

Stunning Mountain Cabin w/ Pool & Hot Tub

Lake Retreat: Families, Firepit, BBQ, KING Bed, AC

Experience The Zen House

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

Private Game house-Basketball*Hot Tub*Jacuzzi*Gym

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

Villa MiaNova A Modern Hideout in the Woods
When is the best time to visit Smallwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ683 | ﺩ.ﺇ698 | ﺩ.ﺇ654 | ﺩ.ﺇ606 | ﺩ.ﺇ698 | ﺩ.ﺇ646 | ﺩ.ﺇ757 | ﺩ.ﺇ797 | ﺩ.ﺇ698 | ﺩ.ﺇ679 | ﺩ.ﺇ698 | ﺩ.ﺇ716 |
| Avg. temp | -2°C | -1°C | 3°C | 10°C | 16°C | 21°C | 23°C | 22°C | 18°C | 12°C | 6°C | 1°C |
Quick stats about vacation rentals that are family-friendly in Smallwood

Total vacation rentals
Explore 80 vacation rentals in Smallwood

Nightly prices starting at
Smallwood vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 4,630 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
80 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!
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- Pet-friendly rentals Smallwood
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- Family-friendly rentals Sullivan County
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- Family-friendly rentals United States
- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Bushkill Falls
- Montage Mountain Resorts
- Elk Mountain Ski Resort
- Minnewaska State Park Preserve
- Camelback Snowtubing
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Sunset Hill Shooting Range
- Aquatopia Indoor Waterpark
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Ringwood State Park
- Promised Land State Park
- Mount Peter Ski Area
- The Country Club of Scranton
- Wawayanda State Park
- Hunter Mountain Resort
- Plattekill Mountain
- Sterling Forest State Park
- Claws 'N' Paws




