Holiday rentals in Smallwood

A vibrant red cabin is surrounded by a grassy area, featuring a circle of white Adirondack chairs positioned around a fire pit. A wooden deck with railing extends from the cabin, while the backdrop includes trees and a clear blue sky.

4.98 out of 5 average rating, 120 reviews

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.

Superhost

The open living area features a comfortable seating arrangement with a neutral-colored couch and a patterned area rug. A TV stand with a television is situated against one wall. The loft and bedroom are visible in the background, adding a sense of spaciousness to the layout.

4.84 out of 5 average rating, 246 reviews

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

4.92 out of 5 average rating, 116 reviews

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

A stone path leads to a tranquil outdoor area surrounded by trees, featuring several seating options including adirondack chairs. A flowing stream can be seen in the background, providing a serene backdrop to this private space.

4.97 out of 5 average rating, 272 reviews

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

4.94 out of 5 average rating, 158 reviews

Fireplace—Renovated—Near Skiing & Tubing—Chic+Cozy

Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat with a cozy fireplace & fire pit in a woodland backyard. 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.

4.95 out of 5 average rating, 165 reviews

Cottage in Kenoza Lake

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

4.99 out of 5 average rating, 227 reviews

The A-frame cabin is surrounded by trees and set on a grassy area. A fire pit with seating is situated in front, with smoke rising gently in the evening light. The cabin's large windows reveal a welcoming interior, illuminated by natural light.

Home in Bethel

BirchRidge A-Frame: Sauna/Firepit/King Bed/7 Acres

Nestled in the Catskills Forest, less than 2 hrs from NYC, you'll find Birch Ridge A-frame! This gorgeous 2-bedroom cabin is set on 7 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that creates a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

A warm living area is highlighted by a wood-burning stove at its center, surrounded by a cowhide rug. Light-colored armchairs are positioned alongside a wooden coffee table. Natural light enters through multi-pane windows, complemented by a guitar and decorative plants against the walls.

4.93 out of 5 average rating, 151 reviews

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.

4.92 out of 5 average rating, 166 reviews

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

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.

4.91 out of 5 average rating, 364 reviews

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.

4.92 out of 5 average rating, 474 reviews

Home in Narrowsburg

Cutest Little House in Narrowsburg

Relax in an idyllic wooded setting with 1000 feet of totally private river frontage, yet a 5 minute drive to Narrowsburg's restaurants and shops. If you like nature, privacy, history, vintage decor & design, this quaint 1950s cottage is for you. Hiking & campfires • Clawfoot tub • Front & back porches • Hummingbird & bunny watching • Den & WiFi • Peace & quiet • All included in your stay! Hundreds of 5-star reviews say it all. IG: #luxtonlake #tenmileriver #cutesthousenarrowsburg

Shipping container in Bethel

An outdoor area showcases multiple seating options, including six Adirondack chairs arranged around a fire pit. The backdrop is formed by a modern container home surrounded by colorful autumn foliage, complemented by a deck and outdoor dining setup, enhancing the serene atmosphere.

4.98 out of 5 average rating, 106 reviews

Hot Tub, Fire Pit, Games, PizzaOven, Holiday Decor

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 your stay today and experience the charm of container living! Message me for Q's!

Popular amenities for Smallwood holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Smallwood

Cabin in Livingston Manor

A cozy living area features large windows offering views of the surrounding woods. The space includes a plush light grey sofa, black accent chairs, and a wooden coffee table. A warm-toned rug and soft, textured cushions add comfort to the ambiance.

4.98 out of 5 average rating, 95 reviews

The Ensconce: Modern cabin in the woods

4.96 out of 5 average rating, 98 reviews

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

Luxe & Modern farmhouse | House of Jane West

4.93 out of 5 average rating, 58 reviews

A quaint cabin is framed by lush green trees and surrounded by a well-maintained garden. A stone pathway leads to the front door, which is painted a welcoming blue. Natural sunlight brightens the exterior, creating a serene outdoor atmosphere.

Cottage in Bethel

Cozy Cabin in the Catskills

5 out of 5 average rating, 93 reviews

The exterior of the modern structure features large windows and a sloped roof. A wooden deck is highlighted with two red chairs and decorative planters filled with greenery and flowers. Soft sunlight illuminates the space surrounded by trees.

Guest house in Callicoon

R52Creekside one bedroom cottage

4.98 out of 5 average rating, 66 reviews

A cozy cottage is nestled among tall trees, featuring a gray exterior and a chimney with smoke gently rising. Warm light glows from the windows, suggesting a welcoming interior. Lush greenery surrounds the base, enhancing the natural setting.

Home in Narrowsburg

Lake Ridge Bungalow w/ outdoor SAUNA

4.95 out of 5 average rating, 63 reviews

Design Cabin in Catskills | Hot Tub + Sauna+ Pizza

Guest house in Callicoon Center

A charming guesthouse exterior features a bright red door, framed by green plants and a welcoming bench. Pathway stones lead to the entrance, while a wooden barn stands in the background, surrounded by lush greenery.

4.98 out of 5 average rating, 52 reviews

Indigo Bunting Farms MilkHouse/Sauna & Cold Plunge

A charming cottage exterior is shown, featuring a log cabin design with a blue roof and teal trim around the windows. Adirondack chairs are positioned on the wooden deck, inviting relaxation. The surrounding trees enhance the natural setting.