Pet-friendly holiday rentals in Smallwood

5 out of 5 average rating, 252 reviews

The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.

Cabin in Margaretville

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

The cabin is softly illuminated by outdoor string lights at dusk, creating a welcoming atmosphere. A stone pathway leads to a fire pit surrounded by four Adirondack chairs, while the cabin's deck features inviting seating. Lush trees provide a natural backdrop.

4.94 out of 5 average rating, 180 reviews

Canoe—SUPs—Innertubes—Chic—Renovated—Fire Pit—BBQ

'The Original Bungalow,' part of the @boutiquerentals_' collection, is a Scandi-chic renovated bungalow surrounded by stunning trees. Located only 2 hours from NYC, Smallwood is a destination in itself: walk along the lake or waterfall, or take the canoe or SUPs for a paddle (seasonal). Nearby are Bethel Woods Center for the Arts, breweries, Livingston Manor & cute Delaware River towns with dining+shopping. In the evening, unwind by the fire pit or curl up by the fireplace with a book or movie.

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, 288 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

A serene view of a lake during sunset, taken from a pedal boat with a dog sitting beside a guest. Calm waters reflect the warm colors of the sky, while the silhouette of trees borders the horizon.

4.92 out of 5 average rating, 131 reviews

hot tub–pedal boat+paddle boards–fire pit–bbq–chic

Escape to @boutiquerentals_' The Treehouse Bungalow – a cozy renovated 1930s Arts & Crafts cabin with hot tub, fire pit, mountain/treehouse views, Scandi-chic decor, picnic table & BBQ. Just 2 hours from NYC in the Catskills with seasonal lake access, pedal boat & paddle boards, waterfall, forest trails & proximity to Delaware River tubing/rafting. Visit antique shops, Bethel Woods Center for the Arts, Kartrite Waterpark, breweries & charming towns like Callicoon, Narrowsburg & Livingston Manor

4.92 out of 5 average rating, 163 reviews

A wooden deck is softly illuminated by candlelight, creating a serene atmosphere. A staircase leads to a wooden hot tub surrounded by lush foliage. The evening sky, deepening into twilight, adds to the tranquil ambiance of the outdoor space.

Cabin in Monticello

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.

Superhost

Two black Adirondack chairs are placed beside a small round table on a wooden deck, overlooking Kauneonga Lake. The sunset casts soft hues across the water, while the shoreline and trees are silhouetted against a colorful sky.

Apartment in Kauneonga Lake

4.85 out of 5 average rating, 198 reviews

Lakeside Studio on White Lake

This lovely studio rests on the shore of the beautiful Kauneonga Lake. The newly renovated interior creates a warm and relaxing space to take in the amazing sunset views over the lake. The studio is part of a larger building but has private rear yard access, all other spaces are on the road side. Located on Restaurant Row and just a few minutes away from the Historic Bethel Woods Center for the Arts (Home of the original Woodstock). * In the summer months we have boat slips directly in front.

4.94 out of 5 average rating, 162 reviews

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.

Cabin in Monticello

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.

4.99 out of 5 average rating, 268 reviews

A serene outdoor seating area features two wooden chairs positioned beside a stone platform. A fire pit with a crackling flame is set in front of the chairs, overlooking a gently flowing creek and lush greenery, creating a tranquil nature retreat.

Cabin in Millrift

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

4.98 out of 5 average rating, 221 reviews

Cabin in Yulan

Enchanting River A-Frame|Fire Pit| Magical Forest

Escape to our Magical Riverside A-Frame on 4 secluded acres. Swim in the enchanting river, grill dinner under the trees, and gather by the fire pit beneath twinkling string lights & a sky scattered with endless stars. Watch deer, eagles & fireflies as you unwind in this cozy 2BR cabin. Perfect for couples, nature lovers, and anyone craving a peaceful retreat. Minutes from scenic hikes & Delaware River adventures connecting deep with nature - leave feeling like you stepped out of a storybook.

5 out of 5 average rating, 103 reviews

A modern home features a sleek design with dark wood siding and red accents. Large windows provide ample natural light, while a spacious deck extends outwards, furnished with lounge chairs. The surrounding landscape consists of lush grass and trees, creating a serene atmosphere.

Home in Narrowsburg

Modern Catskills Retreat•10 Acres•Hot Tub•Firepit

Welcome to a dream escape, tranquil 3-bedroom modern home that's less than 1-mile off the Delaware River! Built in 2023 and nestled on 10+ acres of pristine countryside delivering peace, quiet and privacy. This exceptional retreat seamlessly combines rustic charm with contemporary luxury, guaranteeing an unforgettable stay. The home features 3 furnished bedrooms sleep up to 7 (3 queen beds, 1 w/ trundle) + a spacious entertainment room flowing directly from the kitchen ideal for hosting.

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, 128 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, workspace, fast wifi.

Shipping container in Smallwood

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, 119 reviews

Unique Container Home w/ Hot Tub, Fire Pit & More!

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

Popular amenities for Smallwood pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 111 reviews

A two-story farmhouse is surrounded by colorful wildflowers and lush greenery. A wide porch features rocking chairs and bright seating areas. The building is topped with a metal roof and a stone chimney, providing a scenic view against a clear blue sky.

Home in Napanoch

Cozy farmhouse & stunning views on 135 acres

4.97 out of 5 average rating, 153 reviews

A wooden sauna features warm, natural wood paneling and ambient lighting. Two seating benches provide ample space for relaxation, while a small basket holds towels. A window allows for natural light to enter, enhancing the tranquil atmosphere within the sauna.

Home in Parksville

Catskills Retreat / Sauna/ Hot Tub/Bethel Woods

4.95 out of 5 average rating, 195 reviews

Home in Damascus

Delaware River retreat

5 out of 5 average rating, 152 reviews

A spacious living area features high ceilings with wooden beams and large windows showcasing the surrounding trees. A stone fireplace adds warmth, while a modern kitchen with white cabinetry and stainless steel appliances is visible in the background. Three bar stools are positioned at the kitchen island.

Home in Parksville

Catskill Retreat w/ Hot Tub / Near Casino & Roscoe

4.93 out of 5 average rating, 142 reviews

Aerial view reveals a spacious lawn surrounding a modern home by the water's edge. Kayaks are visible near the shore, while the tranquil lake reflects the surrounding greenery. The property showcases open space ideal for relaxation and family activities.

Home in Narrowsburg

Gorgeous Waterfront w/ Hot Tub and Game Level

4.92 out of 5 average rating, 236 reviews

The exterior of the lake house is shown, featuring a blue facade with white trim. A small front deck with steps leads to the entrance. Lush greenery surrounds the property, providing a serene backdrop. A gravel path leads up to the house, enhancing a rural feel.

Home in Rock Hill

Beaver Lake Escape

4.99 out of 5 average rating, 340 reviews

The great room features a rustic stone fireplace as its focal point, surrounded by wooden beams and large windows allowing natural light. Two couches of varying styles are arranged around a wooden coffee table, providing a cozy setting for gatherings.

Home in Callicoon

Paradise in the Catskills

4.99 out of 5 average rating, 159 reviews

A cozy cabin nestled among vibrant autumn foliage features rich reds and yellows amidst a forest of tall trees. The surrounding area holds scattered rocks and a rustic fire pit area, creating a natural and inviting outdoor space.

Home in Glen Spey

Lakehouse Getaway/Winter/Summer/Spring/Fall

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 296 reviews

An elegant bathroom features a freestanding soaker tub positioned by a large triangular window. Natural light floods the space, showcasing views of surrounding trees. A small green stool complements the decorative patterned tile floor, while potted greenery adds a touch of nature.

Cabin in The Hideout

Mid-century A-frame nestled amongst the trees

Superhost

An inviting living space showcases expansive floor-to-ceiling windows, allowing natural light to illuminate the room. A cozy sofa is complemented by stylish chairs, while a large area rug unifies the seating arrangement. Dining space is visible in the background, enhancing the open floor plan.

Cabin in Swan Lake

4.84 out of 5 average rating, 236 reviews

Catskills Modernist Cabin Pool Hot Tub

Guesthouse in Olivebridge

A charming red cottage is set against a backdrop of lush greenery and blue skies. The landscaped yard features well-maintained grass and a variety of trees, providing a serene outdoor environment. Nearby, an additional outbuilding is visible, enhancing the rustic atmosphere.

4.93 out of 5 average rating, 281 reviews

Sweet Fern Cottage With Saltwater Pool

4.88 out of 5 average rating, 105 reviews

Cabin in Woodbourne

Cheerful 3-bedroom Cabin in the Woods with a pool.

Cabin in Livingston Manor

An inviting hot tub is positioned on a wooden deck, overlooking a spacious backyard and the tastefully designed home. Soft lighting enhances the outdoor setting as sunset hues paint the sky, creating a serene atmosphere perfect for relaxation.

4.97 out of 5 average rating, 347 reviews

Experience The Zen House

4.98 out of 5 average rating, 151 reviews

A wooden exterior is complemented by solar panels on the roof, showcasing sustainability. Surrounding foliage displays autumn colors, with trees and shrubs framing the entrance. The home features a welcoming porch area leading to large glass doors that invite guests inside.

Chalet in Mount Tremper

Secluded Woodstock Retreat -Heated Pool and Sauna

4.91 out of 5 average rating, 116 reviews

An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.

Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

4.95 out of 5 average rating, 393 reviews

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

Fenced & Salt Water Pool | Cozy Catskills Cottage

Private, pet-friendly home rentals

4.98 out of 5 average rating, 107 reviews

Cabin in Cuddebackville

Riverfront Retreat | Hot Tub, Firepit & Pool Table

4.97 out of 5 average rating, 191 reviews

Early morning mist gently blankets the lawn, highlighting lush greenery. A log home is visible in the distance, with large windows reflecting the soft glow of the rising sun. The serene river complements the peaceful scene, inviting relaxation and connection with nature.

Cabin in Narrowsburg

Private Riverfront, Magestic View, Wildlife, Sauna

4.99 out of 5 average rating, 120 reviews

A modern cottage exterior is shown, featuring a spacious deck that leads to a grassy area. Adirondack chairs are arranged on the deck, accompanied by a BBQ grill nearby. The cottage has a striking dark facade with a red roof and a welcoming wooden door.

Cottage in Accord

Peaceful Cottage-in Private 5-acre field

4.96 out of 5 average rating, 77 reviews

Cabin in Monticello

Design Cabin in Catskills | Hot Tub + Sauna+ Pizza

A charming cabin nestled among lush green trees features a striking black exterior with red accents and a green metal roof. The deck, with stairs leading up from the gravel driveway, offers a welcoming entrance to the inviting retreat.

4.99 out of 5 average rating, 79 reviews

The little cabin that could…Catskills Cutie

5 out of 5 average rating, 10 reviews

Welcome to Your Peaceful Retreat

5 out of 5 average rating, 195 reviews

A charming 1930's cottage is set against a backdrop of vibrant autumn foliage. The structure is surrounded by a spacious lawn, leading to glimpses of the river nearby. Brightly colored leaves adorn the trees, contributing to the serene and natural atmosphere.

Cottage in Narrowsburg

Upper Delaware River cottage