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House vacation rentals in Smallwood

Find and book unique houses on Airbnb

Quick stats about house rentals in Smallwood

  • Total vacation rentals

    Explore 20 vacation rentals in Smallwood

  • Nightly prices starting at

    Smallwood vacation rentals start at G$29,260 GYD per night before taxes and fees

  • Verified guest reviews

    Over 920 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 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 house rentals in Smallwood

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
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
4.95 out of 5 average rating, 172 reviews

1913 Love Shack2miles from Bethelwoods big jukebox

90 mins NYC WHITE LAKE SULLIVAN COUNTY Bethel Countryside. Bethel Cabin Very quiet Rustic Romantic Log Cabin1913 modern 3bedroom Situated looking over White Lake.Sit and enjoy the warm fire while watching TV Free PLAY JUKE BOX FOOSBALL PINGPONG, Private 300 acres come get grounded in nature walk around with husband boyfriend, Girlfriend or wife, and Dogs. 2 miles to Bethel Woods where Woodstock was WIFI 2 smart TVS 6 LOCAL BREWERY'S Clean Towels, Sheets. Avoid future regret book today. Bethel

Top guest favorite
An inviting open living space features large windows that allow natural light to flood the room. The area includes a comfortable seating arrangement with a beige sofa and armchair, alongside a round coffee table. The dining area is visible through a set of French doors that lead to a large deck.
Home in Woodridge
4.96 out of 5 average rating, 104 reviews

Serene Home in the Catskills Woods

Welcome to your countryside escape! Perched in the heart of scenic Sullivan County, Davos on the Hill is your serene home away from home—the ultimate retreat for hiking, rest, and recharging. We’ve curated a space that balances minimalist design with total comfort. Whether you’re whipping up a gourmet meal, ordering a local pizza for movie night, or gathering for board games by the fireplace, you’ll find everything you need right here. Slow down, breathe deep, and make some memories.

Top guest favorite
Home in Damascus
4.95 out of 5 average rating, 198 reviews

Delaware River retreat

Approximately two hours from the GW bridge - this beautiful country home is located directly on the Delaware River. The house features a full kitchen, a large dining room, and two porches that overlook the river. Watch the eagles, warm up by the fireplace, ski, hike, fish, canoe, swim, eat and laze about. With hi-speed cable and WiFi, tons of space inside and out, this house is perfect for a getaway, staycation, or for families and couples looking to remote-work.

Top guest favorite
Home in Kerhonkson
4.96 out of 5 average rating, 105 reviews

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

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
4.96 out of 5 average rating, 423 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Superhost
Home in Swan Lake
4.96 out of 5 average rating, 104 reviews

Bethel Woods Escape: Private Oasis

Welcome to Bethel Woods Escape - a gorgeous modern home surrounded by woodlands of Eastern pine and hemlock trees. In 1969 Bethel Woods was home to the notorious Woodstock festival. Located in the country hills of the Sullivan Catskills, Bethel Woods is an amazing place to explore, hike, and listen to live music. Just 5 minutes away from Bethel Woods Center of the Arts, you will find a stunning A-Frame home waiting to host your next adventure.

Top guest favorite
A modern house with a large glass wall is nestled among tall trees beside a serene waterway. A spacious deck extends from the home, offering a view of the surroundings. The landscape features a gently sloping yard leading to the water's edge.
Home in Monticello
4.97 out of 5 average rating, 175 reviews

Secluded lakefront home With an EV charger

Welcome to your oasis on the Swiniging Bridge Reservoir! Only 90 minutes from NYC, but a world away. A complete glass wall facing the water allows guests to take in the views and sounds of a babbling brook that feeds into a motorboat lake. This brand new house sleeps 6 adults (or 4 adults and 3 children) and features a full kitchen, free WiFi, bedding, linens, and toiletries. A canoe and paddleboat are also available for your use!

Guest favorite
A modern bedroom features a deep blue accent wall with illuminated text reading 'Make love not war'. A king-size bed is adorned with yellow and gold pillows, complemented by soft lighting from two bedside lamps. Plush, round seating creates a cozy touch in front of the bed.
Home in Bethel
4.94 out of 5 average rating, 101 reviews

Groovy Getaway at Bethel Woods

Welcome to the Groovy Getaway at Bethel Woods! It is just a 3 minute drive to Bethel Woods Center for the arts, most famously known for the original 1969 Woodstock Festival. This 750 Sq ft newly renovated home is perfect for couples and friends looking to get away and relax right in the heart of the Catskills. The decor is modern yet retro with plenty of space indoors and outdoors to make yourself right at home.

Top guest favorite
A modern dining area features a white table surrounded by four chairs, positioned beneath a sculptural light fixture. A soft area rug lies underfoot, complemented by a cozy propane fireplace with a rounded design. Large glass doors open to a view of the backyard.
Home in Livingston Manor
4.97 out of 5 average rating, 115 reviews

Luxe & Modern farmhouse | House of Jane West

Imagine Morticia Addams vacationed in Scandinavia - worked remotely with fast streaming wifi, and then influenced the design of a 1920’s farmhouse in Upstate New York to function both as a remote worker’s dream and an NYC office worker's ideal getaway weekend. In our case, Morticia Addams is known as Jane West, and she was the inspiration for our first weekend home.

Top guest favorite
Home in Narrowsburg
4.92 out of 5 average rating, 132 reviews

Modern Secluded Retreat

Discover a secluded paradise on 11+ acres with a stream, pond, and woods. This private Airbnb features a one-bedroom with a king bed, a large bathroom, open-plan living area, and a deck with stunning views. The property includes a game room/studio with heated floors for yoga or fitness, plus a 1/2 bath. Perfect for nature lovers seeking tranquility and comfort.

Guest favorite
A sunlit living area features a modular sofa adorned with dark cushions, complemented by two vibrant orange tables. A freestanding black propane stove adds warmth, while light-colored wood accents and beams create a minimalistic aesthetic. A cozy rug lies beneath, enhancing the inviting atmosphere.
Home in Kerhonkson
4.98 out of 5 average rating, 328 reviews

Cook House, Modern Cottage with Hot Tub

Cook House is a renovated Catskills cottage by Reset Club — featured in Vogue, Curbed, and Remodelista. Made for weekends where dinner matters, records are on, and the evening takes its time. Professionally laundered Parachute linens, Wonder Valley bath products, and Sonos throughout. One of four Reset Club properties in the Catskills.

Top guest favorite
Home in Liberty
4.99 out of 5 average rating, 126 reviews

Creekside Retreat•Fire Pit•Game Room•Dog Friendly

A creekside Catskills retreat for families, friends, and dogs. Spend your days exploring the private creek and swimming hole, and your evenings around the fire pit while the kids enjoy ping pong and shuffleboard. • Private creek & swimming hole • Sleeps 8 • Game room • Fire pit & deck • 10 min to Livingston Manor • Dog friendly

Popular amenities for Smallwood house rentals

When is the best time to visit Smallwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$56,221 GYDG$42,845 GYDG$39,710 GYDG$39,292 GYDG$64,163 GYDG$41,382 GYDG$57,684 GYDG$62,700 GYDG$54,967 GYDG$49,742 GYDG$57,475 GYDG$58,102 GYD
Avg. temp-2°C-1°C3°C10°C16°C21°C23°C22°C18°C12°C6°C1°C
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