
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 ﺩ.ﺇ514 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.

1913LoveShack Memorial Day open avoidfuture regret
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

Maple House Picturesque Catskills Getaway +Hot Tub
Maple House is a renovated mid century modern Catskills home. Nestled on 6 private acres the house is perched upon a hill providing perfect seclusion despite being an easy walk into Jeffersonville and a quick ride into Callicoon, Livingston Manor, Roscoe, Narrowsburg, Bethel and Catskill Park. The comfortable living space features a fireplace, record player, home theater and lots of spaces to relax.The grounds offer an outdoor deck, hot tub, a fire pit, hammocks plus forested acres to explore.

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.

Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

In the clouds your cozy- lake house
Cozy lake house in Catskill,only 2 hrs away from NYC.The property has 2 Bedroom 1-1/2 baths & sleeps 4-6 people. Guest can enjoy kayaking fishing in property.The property is close proximity 2 downtown Jeffersonville & Bethel-Woods Center for Arts (Historic Site of the 1969 Woodstock Music & Art Fair).Nearby attractions ~ Villa Roma Resorts,Resort World Casino, Kartrite Resort & Water park & Holiday Mountain Ski resort.Visit local farms and Catskill brewery

Stone Creek House: A Tranquil Family Getaway
Welcome to Stone Creek House, a creekside, family retreat made for gathering and unhurried days. Ten minutes from Livingston Manor, a light-filled home offers both comfort and charm. The property features a private creek, a large deck with ample seating, a grill and field for games. Inside, you’ll find a game room and a two-sided fireplace that warms both the living + dining rooms. Stone Creek House is a place to slow down, spread out, and settle in.

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.

Bethel Woods Escape: Private Oasis w/ Fire Pit
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.

ENTER HOME - Minimalistic style warm & inviting
ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only

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.

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.

6-Acre Narrowsburg Estate: Private Pool, Hot-Tub
A modern 3BR/2BA Catskills retreat on 6 acres with a private pool, hot-tub and fireplace. 10 mins away from Narrowsburg's Town Center with shops and restaurants, this house is perched on a hill, offering serenity and scenic views. Enjoy modern decor, premium bedding, AC, and fast Wi-Fi. Pool season for 2026: May 22nd - Sept 14th. Hot tub is always open.
Popular amenities for Smallwood house rentals
House rentals with a pool

Oak View: Firepit, BBQ, and Sonos Sound!

Private Retreat w/Pool, Hot Tub & Fire Pit, 6 BR

Lakeside Oasis

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

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

Trout fishing on the Delaware

Spacious Catskills Farmhouse on over 5 acres!
Fenced & Salt Water Pool | Cozy Catskills Cottage
Weekly house rentals

Wellness Retreat w/ Hot Tub, Gym, Cold Plunge

Luxury Mountain Retreat with Panoramic Vista Views

Delaware River Hideaway

Hot Tub, Sauna & Fireplace Private Catskills Stay

Private Forest Getaway • Fire Pit • Bethel Woods

Lakefront A-Frame w/ Hot Tub & Game Room!

Catskill Mountains Forest Nest for 2

Groovy Getaway at Bethel Woods
Private house rentals

Scott Brook Cabin

Cozy Cottage in Sullivan County Catskills

Forest Art House • Spacious • Hot tub • Firewood

Catskills Forest Cabin w/ Deck, Sauna and Gym

Peaceful Escape • Hot Tub • Fire Pit • Views

eco & wellness cabin: with hot tub + sunroom

Lakefront Home on Woodstock Way

3BR Catskills Getaway Retreat!
When is the best time to visit Smallwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ771 | ﺩ.ﺇ764 | ﺩ.ﺇ687 | ﺩ.ﺇ690 | ﺩ.ﺇ1,127 | ﺩ.ﺇ727 | ﺩ.ﺇ1,014 | ﺩ.ﺇ1,102 | ﺩ.ﺇ966 | ﺩ.ﺇ874 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,021 |
| 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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- Rentals with beach access Smallwood
- Rentals with a fireplace Smallwood
- Rentals with a fire pit Smallwood
- Cabin rentals Smallwood
- Rentals with outdoor seating Smallwood
- Family-friendly rentals Smallwood
- Rentals with a patio Smallwood
- Pet-friendly rentals Smallwood
- Rentals with lake access Smallwood
- Rentals with a washer and dryer Smallwood
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- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Elk Mountain Ski Resort
- Bethel Woods Center for the Arts
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