
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.

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

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.

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 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!

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

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.

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.

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!

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.

Mid-Century Cottage | Lovely Yard | Fast Wifi
Stylishly designed mid-century retreat surrounded by nature • Livingston Manor & Jeffersonville 12 min •. Bethel Woods Center for the Arts 17 min. • Great for couples or small families • Walnut Mt. hiking 8 min. • Gas grill & fire pit • Rocking chair front porch • 2 queen bedrooms, open living area, 1 bathroom. • Fully-stocked kitchen/beautiful cabinets and open shelves. • Relax inside or explore the backyard's natural beauty. •. Enjoy fast internet Your unique escape awaits!

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, workspace, fast wifi.
Popular amenities for Smallwood family-friendly rentals
Family-friendly home rentals with a hot tub

the tree house, Wood Fired Hot Tub/Barrel Sauna

Lovely Cottage w/ Jacuzzi+Access to Nearby Lakes!

Private Catskills Spa: Sauna, Hot Tub, Cold Plunge

Private Riverfront Catskills Retreat w/ Hot Tub

Chic Cabin on Callicoon Creek

Riverfront Retreat | Hot Tub, Firepit & Pool Table

Mural Art Cabin With Pond And Hot Tub

Lakefront • Hot tub • Kayaks • Fire Pit • Fishing
Family- and pet-friendly home rentals

Enchanting River A-Frame|Fire Pit| Magical Forest

1913 Love Shack Cheap week2miles from Bethelwoods

Creekside Retreat•Fire Pit•Game Room•Dog Friendly

Remote Waterfall Cabin at Swiftwater Acres

Peaceful creekside retreat near Livingston Manor

Upper Delaware River cottage

Lakeside Studio on White Lake

Private Riverfront, Magestic View, Wildlife, Sauna
Family-friendly home rentals with a pool

Bella Cottage w/Pool, BBQ - Catskill Getaway

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

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

Secluded Cool Summer Cabin with mini pool

Luxe modern A Frame, Hot tub and new heated pool

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

Experience The Zen House

Au Bon Orchard - Hot Tub - 56 Private Acres
When is the best time to visit Smallwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 738 | ﺩ.ﺇ 661 | ﺩ.ﺇ 591 | ﺩ.ﺇ 650 | ﺩ.ﺇ 709 | ﺩ.ﺇ 690 | ﺩ.ﺇ 757 | ﺩ.ﺇ 797 | ﺩ.ﺇ 698 | ﺩ.ﺇ 687 | ﺩ.ﺇ 683 | ﺩ.ﺇ 712 |
| 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 |
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- Hunter Mountain
- Mountain Creek Resort
- Bushkill Falls
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Montage Mountain Resorts
- Elk Mountain Ski Resort
- Minnewaska State Park Preserve
- Bethel Woods Center for the Arts
- Camelback Snowtubing
- Sunset Hill Shooting Range
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Promised Land State Park
- Aquatopia Indoor Waterpark
- Storm King Art Center
- Plattekill Mountain
- Mohonk Preserve
- Peekamoose Blue Hole
- Mountain Creek Water Park
- Hunter Mountain Resort
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area





