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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$31,400 GYD per night before taxes and fees

  • Verified guest reviews

    Over 960 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 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
4.94 out of 5 average rating, 173 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

Guest favorite
A stylish kitchen area features dark cabinetry and a large island with seating. The ceiling is adorned with decorative wallpaper, while modern lighting fixtures create a warm atmosphere. A black refrigerator and oven are visible, along with various kitchenware displayed on open shelves.
Home in Eldred
4.93 out of 5 average rating, 106 reviews

Stylish river town escape with hot tub + fire pit

Kick back and relax in this calm, stylish space. A designer renovated 1920s cottage in the Catskills on a windy road near the Delaware River. Hideaway 2 hours from NYC and short drive to restaurants and retail in Barryville, Narrowsburg & Callicoon. This cottage hosts 2 bedrooms, open living, dining and kitchen, a bathroom with a rain shower and a mudroom with laundry. The larger bedroom features a workspace. The yard is now fully fenced, has a BBQ grill, fire pit, outdoor dining and hot tub.

Superhost
Home in Narrowsburg
4.92 out of 5 average rating, 237 reviews

3BR/2BA • Private Pool & Hot Tub Near Bethel Woods

A modern 3BR/2BA Catskills retreat with a private pool, hot-tub and fireplace. 10 mins away from Narrowsburg's shops and restaurants as well as Delaware River access for swimming and hiking. 15 mins to Bethel Concerts. Perched on a hill, offering scenic views and serenity- a true getaway destination. Enjoy modern decor, premium bedding, AC, fast Wi-Fi, and purest water that you’ll find. Swim, grill, play ping-pong, darts, star gaze. Pool season ends 9/14th. Hot tub is always open.

Guest favorite
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
4.92 out of 5 average rating, 177 reviews

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.

Guest favorite
A spacious living area is highlighted by large windows allowing natural light to fill the space. The hardwood floor complements a dining table with chairs, and a cozy seating arrangement near a fireplace. Decor includes plants and a guitar in the corner.
Home in Parksville
4.96 out of 5 average rating, 215 reviews

Cooley Mountain House *Hot Tub*

Remove the walls between you and nature in this spacious, vaulted and sun-drenched getaway. Nestled along a mountain stream on a quiet country road in the heart of the western Catskills, this fully redesigned house blends modern comforts with rustic styling, offering you and your guests an open invitation to kickback, “work from nature” or keep playing til sunrise. Under two hours from NYC, and less than 15 minutes from Livingston Manor, Cooley Mountain House keeps everything within reach.

Guest favorite
Home in Narrowsburg
4.93 out of 5 average rating, 146 reviews

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to Jay’s Big Sky! Here are a few things I think you’ll especially enjoy about the house. Highlights - You’ll love the: • Location - quiet, waterfront position on 27 acre lake • Hot tub (all year) - a relaxing treat after hiking, skiing, or exploring • Family-perfect layout - 2 levels, with full game / media level • Fast WiFi & dedicated workspace - ideal for remote work • Kayaks and life-vests - for safe water fun!

Top guest favorite
Home in Narrowsburg
4.92 out of 5 average rating, 135 reviews

Modern Secluded Retreat

Escape to the center of 11+ acres of woods, water, and dark starry skies—under 2 hours from NYC. Walls of windows pull the outside in, with a stream, pond, and constant wildlife just beyond. Warm up by the fireplace, unwind in the open living space, and sleep deep in a king bed. A large jetted bathtub, bonus half bath, and a flexible bonus room with pool table and ping pong table on heated floors round it out. Peaceful, private, and made for slowing down.

Top guest favorite
Home in Kerhonkson
4.96 out of 5 average rating, 106 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.

Superhost
Home in Swan Lake
4.95 out of 5 average rating, 105 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.

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, 105 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, 116 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.

Guest favorite
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
4.91 out of 5 average rating, 265 reviews

Dancing Feather: Cozy Lake-Front A-Frame Chalet

Sunlight pours into every room at this delightful lake front A-frame cabin. Enjoy a cozy fireside dinner with friends or an evening under the stars with warm blankets provided. Appreciate the quiet and tranquility that is found here on the lake. Create unforgettable memories at this peaceful lake front home.

Popular amenities for Smallwood house rentals

When is the best time to visit Smallwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$56,310 GYDG$42,913 GYDG$39,773 GYDG$39,354 GYDG$64,264 GYDG$41,447 GYDG$57,775 GYDG$62,799 GYDG$55,054 GYDG$49,821 GYDG$57,566 GYDG$58,194 GYD
Avg. temp-2°C-1°C3°C10°C16°C21°C23°C22°C18°C12°C6°C1°C
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