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Vacation rentals in Smallwood

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Quick stats about vacation rentals in Smallwood

  • Total vacation rentals

    Explore 90 vacation rentals in Smallwood

  • Nightly prices starting at

    Smallwood vacation rentals start at G$12,539 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Smallwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Smallwood rentals

  • 4.8 Average rating

    Smallwood stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Smallwood

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

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Guest favorite
Cabin in Smallwood
4.94 out of 5 average rating, 183 reviews

Lake Access—Canoe—SUPs—Innertubes—FirePit—BBQ—Chic

Only 2 hours from NYC, stay at @boutiquerentals_' Scandi-inspired 'The Original Bungalow' in the Catskills featuring lake access, canoe, paddle boards+ inner tubes. Come for the ample swimming opportunities, pretty strolls along the lake, forest hikes, Bethel Woods Center for the Arts, original Woodstock site, proximity to the Delaware River, craft beverage trail & charming river towns with great dining+shopping. At night, grill up some delights on the BBQ & relax on the deck or by the fire pit.

Top guest favorite
Cabin in Smallwood
4.97 out of 5 average rating, 293 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

Guest favorite
Cabin in Smallwood
4.92 out of 5 average rating, 135 reviews

Lake Access Plunge Pool Pedal Boat SUPs Fire Pit

Perched on the edge of nature, the 1930s Arts & Crafts cabin 'The Treehouse Bungalow'— part of the @boutiquerentals_ collection — offers lake access, pedal boat & SUPs, plunge pool/hot tub, swimming opportunities, treehouse views, Scandi-chic decor, modern kitchen+bathroom, fire pit, picnic table & BBQ. Explore the hamlet's own waterfall & forest trails or visit Bethel Woods Center for the Arts, breweries & charming towns like Callicoon. For a scenic adventure, go tubing on the Delaware River.

Guest favorite
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
4.92 out of 5 average rating, 167 reviews

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.

Guest favorite
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
4.93 out of 5 average rating, 167 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.

Top guest favorite
Cabin in Smallwood
5 out of 5 average rating, 112 reviews

Cozy Cottage Retreat @ Deerview Cottages LLC

Welcome to Cozy Cottage Retreat where the deer and nature are plentiful. This charming cottage is perfect for a couples retreat and has been totally renovated. The studio style area, host a king size bed, spacious bathroom, laundry, full kitchen, reclining love seats and air conditioner. Smallwood is a Hamlet of Bethel, NY and is centrally located to a host of restaurants and attractions to include: Bethel Woods Summer Concerts, Resort World Casino, Kartrite Indoor Waterpark and Legoland.

Top guest favorite
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.
Cabin in Smallwood
4.99 out of 5 average rating, 81 reviews

The little cabin that could…Catskills Cutie

Catskills Cutie in the heart Bethel Woods village Forest Reserve in the hamlet of Smallwood. 5.5 miles from the Bethel Woods Center for the Arts music venue where Woodstock took place in 1969. You’ll find hiking, biking trails, horseback riding, waterfalls, 5 lakes, 2 large fenced in dog fields, plenty of spots to sit back, relax and decompress from city life. I’ve put a lot of love into this cabin and will continue to add to that. It’s very beautiful, unique & peaceful here. Stay awhile.

Top guest favorite
A two-bedroom log cabin is presented with a dark blue exterior and a welcoming front entrance. Surrounding greenery includes a variety of plants and trees, complemented by a large tree stump nearby. The cabin features a stone foundation and is designed for leisure and comfort.
Cabin in Smallwood
5 out of 5 average rating, 120 reviews

Cozy Lakeside Cabin by Bethel Woods & Casino

This is a 1000 square-foot, two-bedroom log cabin with a sleeping loft. I prefer groups of 4 or less but may accommodate more for an extra fee. Enjoy the new fire pit out back on a cold night. Plenty of board games are available and my kitchen is stocked with spices and cookware. ***5/28/26: Pac-Man arcade pictured needs repair, currently has a faulty display. Walk Mountain Lake, which sits across the street and spans exactly 2 miles around. Or just get some R&R - my beds are so comfy!

Top guest favorite
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.
Cabin in Smallwood
4.98 out of 5 average rating, 132 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.

Top guest favorite
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.
Shipping container in Smallwood
4.98 out of 5 average rating, 124 reviews

Luxury Container Home | Hot Tub & Sky Tub

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 container living! Message me for Q's

Guest favorite
A spacious jacuzzi is set on a wooden deck, surrounded by nature. The water's vibrant blue color reflects the sunlight. Nearby, comfortable black wicker seating can be seen, perfect for relaxing while enjoying the views of the trees.
Cottage in Monticello
4.91 out of 5 average rating, 168 reviews

Lovely Cottage w/ Jacuzzi+Access to Nearby Lakes!

Nestled in the hamlet of Smallwood, only 2 hours from NYC, this newly renovated cottage is the perfect getaway from the city and an oasis surrounded by nature. This cottage is perfectly located for access to surrounding lakes and seasonal beaches, hiking trails as well as exploring and discovering the lovely Catskills region. The cottage features a wood stove, spacious deck, a fire pit as well as an all-season jacuzzi to enjoy day or night.

Guest favorite
A spacious back deck extends from the cabin, surrounded by neatly trimmed bushes. Light string decorations are hung above the area, providing an inviting outdoor space for relaxation. The cabin's rustic siding is complemented by natural surroundings, offering a serene atmosphere.
Cabin in Smallwood
5 out of 5 average rating, 21 reviews

Traditional & Modern Lake Retreat: Yard - Pets OK!

3 BR · 1 BA · Sleeps 7 · Yard · Lake Superior Proximity · Fireplace. Escape to The Smallwood Cabin, a beautifully updated 1935 cabin tucked among towering trees on a half-acre in Smallwood, NY—just 90 miles from NYC. Whether you're sipping coffee on the enclosed porch, cozying up by the stone fireplace, or unwinding on the private back deck, this four-season retreat blends rustic charm with modern comfort.

Popular amenities for Smallwood vacation rentals

When is the best time to visit Smallwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,573 GYDG$37,200 GYDG$33,229 GYDG$33,229 GYDG$36,573 GYDG$36,155 GYDG$38,871 GYDG$41,379 GYDG$36,573 GYDG$36,991 GYDG$36,573 GYDG$35,528 GYD
Avg. temp-2°C-1°C3°C10°C16°C21°C23°C22°C18°C12°C6°C1°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Smallwood?

    Smallwood has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Smallwood?

    Experience the best of Smallwood with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Smallwood?

    Four-legged friends are welcome in Smallwood. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Smallwood?

    Yes! Work meets play with ease at over 50 vacation rentals in Smallwood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Smallwood have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Smallwood. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Smallwood have a kitchen?

    Absolutely! We offer over 10 cottage rentals with a kitchen in Smallwood. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Smallwood have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Smallwood. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Smallwood have free parking?

    Absolutely! We offer over 50 cabin rentals with free parking in Smallwood. Enjoy a tailored experience with all the comforts you desire.

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