
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.

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.

renovated–hot tub–near skiing+tubing–cozy & chic
Escape to @boutiquerentals_' The Treehouse Bungalow–a renovated yet cozy 1930s Arts & Crafts cabin with hot tub, mountain views, fire pit & electric fireplace. Located 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 Center for the Arts & Kartrite Waterpark

Fireplace—Chic & Renovated—Near Skiing & Tubing
Escape to The Original Bungalow, part of the @boutiquerentals_ collection–a newly renovated Scandi-chic retreat with a cozy gas fireplace & woodland backyard with a fire pit. 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

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

Cozy Lakefront Catskills Cabin—2hrs from NYC!
This beautiful lakefront cabin is located at the end of a peaceful road adorned with tire swings and wildflowers. It is situated in a private community on a SMALL 3 acre lake, offering the perfect setting to enjoy morning coffee on the dock, taking refreshing afternoon swims in the lake, going for evening kayaking rides, and stargazing. You can unwind in our hammock nestled amidst the ferns next to a tranquil stream. We offer 2 kayaks and 1 SUP for your enjoyment. Best of all, 2 hrs from NYC.

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.

Lakeside Studio on White Lake
This lovely studio rests on the shore of the beautiful Kauneonga Lake. The newly renovated interior creates a warm and relaxing space to take in the amazing sunset views over the lake. The studio is part of a larger building but has private rear yard access, all other spaces are on the road side. Located on Restaurant Row and just a few minutes away from the Historic Bethel Woods Center for the Arts (Home of the original Woodstock). * In the summer months we have boat slips directly in front.

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.

Hot Tub, Fire Pit/Place, Snow Tubing/Ski Mountain
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 (especially snow safety!)

Cozy Cottage Retreat @ Deerview Cottages LLC
Welcome to Cozy Cottage Retreat where the deer and nature are plentiful. This charming cottage is perfect for a couples retreat and has been totally renovated. The studio style area, host a king size bed, spacious bathroom, laundry, full kitchen, reclining love seats and air conditioner. Smallwood is a Hamlet of Bethel, NY and is centrally located to a host of restaurants and attractions to include: Bethel Woods Summer Concerts, Resort World Casino, Kartrite Indoor Waterpark and Legoland.

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.
Popular amenities for Smallwood family-friendly rentals
Family-friendly home rentals with a hot tub

The Water House - Winter Spa on a Cascading Brook

Cozy and Quiet Lakeview House

Lakefront • Hot tub • Kayaks • Fire Pit • Fishing

Luxury Woodland Escape-Fireplace/Hot tub/Fast WIFI

Renovated Lake House-Hot Tub-Deck-Outdoor Kitchen

The Nest At Swiss - Lakefront In The Catskills

Stunning Mountain Cabin w/ Pool & Hot Tub

Chic Cabin on Callicoon Creek
Family- and pet-friendly home rentals

Luxury Historic School House Cottage

Winter Sale - Cozy Cabin + hiking + pets welcome

The Waterfall Casita: A-frame with 30ft Waterfall

Private Riverfront, Magestic View, Wildlife, Sauna

Modern creekside cabin in the Catskills

Cozy Catskill Getaway Upstate NY - 5 min to casino

Paradise in the Catskills

Modern Farmhouse With Expansive Catskills Views
Family-friendly home rentals with a pool

Lovely 1 Bedroom/Pool/Hot Tub/King Bed/Ski In/Out

Comfy Studio at Mountain Creek Resort

Romantic Log Cabin W/ Hot Tub, Fire Pit, Projector

bungalow summer cottages on the lake Catskills

Bella Cottage w/Cozy Fireplace & BBQ, Fall Getaway

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

Secret Getaway Nestled in a Woodland Setting

Lodge style getaway 50 miles from NYC patio 207
When is the best time to visit Smallwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $267 AUD | $273 AUD | $256 AUD | $237 AUD | $273 AUD | $253 AUD | $296 AUD | $312 AUD | $273 AUD | $266 AUD | $273 AUD | $280 AUD |
| 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 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 $158 AUD 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, Wi-Fi and Pool across Smallwood rentals

4.8 Average rating
Smallwood stays are highly rated by guests—averaging 4.8 out of 5!
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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
- Elk Mountain Ski Resort
- Montage Mountain Resorts
- Bethel Woods Center for the Arts
- Bushkill Falls
- Camelback Snowtubing
- Minnewaska State Park Preserve
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Sunset Hill Shooting Range
- Aquatopia Indoor Waterpark
- Hunter Mountain Resort
- Shawnee Mountain Ski Area
- Plattekill Mountain
- Mount Peter Ski Area
- Brotherhood, America's Oldest Winery
- Promised Land State Park
- Pocono Mountains
- Bear Mountain State Park
- Wawayanda State Park
- Opus 40
- Claws 'N' Paws




