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Holiday rentals with outdoor seating in Callicoon

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Callicoon

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite
A charming cabin exterior showcases a spacious deck with two umbrellas and steps leading down to the lush green yard. A grill is positioned near the entrance, while nearby trees provide shade and enhance the natural surroundings.
Townhouse in Lake Huntington
4.89 out of 5 average rating, 247 reviews

8B Lakeview Duplex New Cabin WiFi - AC- Cable TV

Just Steps to the Sparkling Lake, from this Brand new 100 year old Cabin, set up like a Hotel Room Featuring Private entrance, 2 Queen size beds a deck, BBQ, fire pit, Guest controlled Heat and Air Conditioning, Cable TV, WIFI and Phone. .Row Boats, Kayaks and Canoes available for Guests use on the lake free of charge .120 Acres of Nature trails for Hiking ( Trails closed During Hunting Season, Oct1 to Jan 1 ) .Located Approx. 5 Miles from Bethel woods Concert Center (Woodstock 1969)

Top Guest favourite
The A-frame cabin is nestled among trees, featuring a wooden deck and wide glass doors that open to the interior. A private hot tub is positioned nearby, providing a relaxing outdoor space surrounded by nature.
Cabin in Damascus
5 out of 5 average rating, 209 reviews

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

Top Guest favourite
A spacious living area features large windows allowing natural light and views of the outdoor deck. Comfortable seating is arranged around a coffee table on a patterned rug, complemented by greenery in planters. A standing lamp adds illumination, enhancing the cozy environment.
Home in Liberty
4.99 out of 5 average rating, 121 reviews

Stone Creek House: A Tranquil Family Getaway

Welcome to Stone Creek House, a creekside dog-friendly family retreat. Minutes to Livingston Manor, our light-filled house is designed for gatherings and relaxation. The house has a private creek with a small swimming hole and game room on three acres of landscaped property. A two-sided fireplace keeps you cozy in the living and dining rooms, while the outdoors has a private deck with a chimenea, swing, a field for activities, a fire pit, and a large grill for cooking. photos @stonecreekhouse

Guest favourite
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 Jeffersonville
4.99 out of 5 average rating, 243 reviews

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!

Top Guest favourite
The exterior of a freshly renovated schoolhouse features a welcoming porch with wooden railings and a gabled roof. A central front door is flanked by decorative lanterns and small green shrubs. Two dark, framed windows provide a touch of elegance on either side.
Cottage in Narrowsburg
4.97 out of 5 average rating, 257 reviews

Luxury Historic School House Cottage

Step into history inside our freshly renovated 1800s school house home. Relax and take it easy on the expansive front porch, with sweeping views of rural farmland and a historic cemetery next door. Sit by the fire and enjoy a book or beverage with friends and family and cook a nice farmhouse meal. This unique and tranquil getaway won't disappoint. And it's just 4 minutes from Narrowsburg's Main Street. Swimming holes and hiking trails along the Delaware River are just a stone's throw away.

Top Guest favourite
A quaint cabin sits nestled among tall trees, showcasing a sloped roof and red front door. Adjacent to the cabin is a wooden deck featuring a Finnish sauna and a long table, surrounded by a lush green landscape.
Cabin in Callicoon
4.97 out of 5 average rating, 423 reviews

Chic Cabin on Callicoon Creek

***FEATURED IN ARCHITECTURAL DIGEST, TRAVEL & LEISURE, APARTMENT THERAPY, AND FODORS TRAVEL*** Set back on a small private road, this cabin dating back to the 1800s is perched above the Callicoon Creek, popular with fly fishermen casting for rainbow trout. Head up the wooded driveway and find yourself in a serene, green clearing all your own. The cabin and studio make for a peaceful getaway, shielded from the surroundings, but incredibly convenient for reaching nearby towns and activities.

Guest favourite
The exterior of a modern cabin showcases a deck with two red chairs, inviting relaxation. Large windows create a bright atmosphere, framed by lush greenery. A well-kept lawn enhances the cabin's charming appearance, while the architectural design thoughtfully blends style and comfort.
Cabin in Cochecton
4.98 out of 5 average rating, 123 reviews

Chez Cochecton, a modern cabin in the Catskills

Completely renovated inside and out. This unique cabin style home is built for style and comfort. You'll love the thoughtful design and finishing touches. Enjoy some music and wine while relaxing in the private backyard. Cochecton and neighboring towns of Callicoon and Narrowsburg are full of amazing restaurants, shops and hangouts. Situated just off the Delaware River, this home is very close to swimming, hiking, and kayaking. Enjoy all the beautiful Catskills have to offer all year long!

Guest favourite
A spacious great room features exposed wooden beams and warm wood flooring. In the center, a wood burning stove provides warmth, surrounded by several seating options including rocking chairs and a dining table. Large windows allow natural light to fill the space.
Home in Livingston Manor
4.9 out of 5 average rating, 193 reviews

Butternut Farm Cottage

Butternut Farm Cottage is an 1880's farmhouse. One and a half story great room with wood burning stove, kitchen, dishwasher; laundry room, two bathrooms and library with TV and Wifi. Lots of natural light. Sound system throughout. Covered porch. Comfortable beds. BBQ grill and fire-pit. Good for couples, solo adventurers, business travelers, families, and medium size groups (up to 6). **While not an issue for most some ambient noise from Rt. 17 is heard when outside.

Top Guest favourite
The exterior of a country home is framed by lush trees, with an American flag gently waving from the porch. Flower containers add color along the stone pathway leading to the steps, which provide access to a screened-in area overlooking the river.
Home in Damascus
4.95 out of 5 average rating, 193 reviews

Delaware River retreat

Approximately two hours from the GW bridge - this beautiful country home is located directly on the Delaware River. The house features a full kitchen, a large dining room, and two porches that overlook the river. Watch the eagles, warm up by the fireplace, ski, hike, fish, canoe, swim, eat and laze about. With hi-speed cable and WiFi, tons of space inside and out, this house is perfect for a getaway, staycation, or for families and couples looking to remote-work.

Top Guest favourite
A modern cabin exterior is displayed, featuring a wooden facade and large windows. Snow blankets the ground, and a riverside view provides a peaceful backdrop. A deck leads to the river, surrounded by bare trees, creating a serene winter environment.
Cabin in Livingston Manor
4.95 out of 5 average rating, 117 reviews

Private riverside cabin with soaring ceilings

Newly built riverside cabin overlooking 600ft of private riverfront right on the edge of Livingston Manor. The cabin soaring ceilings and large windows create a light filled space and big views onto the Willowemoc river - stroll down the bank to fly fish one of the areas most famous rivers, or just enjoy looking out over it from your own private deck. After sunset enjoy the outdoor firepit, or indoor stone clad fireplace, or cook a feast from the chef's kitchen.

Top Guest favourite
An inviting living area features a stone fireplace, flanked by large windows that provide scenic views. A combination of leather and fabric seating enhances comfort, while a rustic wooden coffee table sits at the center. Natural light fills the space, creating a warm atmosphere.
Chalet in North Branch
4.99 out of 5 average rating, 136 reviews

Catskills Mountain Chalet l 5 Star experience !

Stylish Chalet in the world famous Catskill mountains privately tucked away on 12 acres surrounded by wildlife and nature. Year-round outdoor activities, fine dining, breweries, and boutique shopping all nearby. Enjoy it all here at Clover Fields! Why "Clover Fields" you ask? Deer visit our property almost daily to graze on our sweet clover fields. It's not uncommon to see them throughout the day. Other notable guests: fox, various birds, woodchucks, chipmunks.

Top Guest favourite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor
4.96 out of 5 average rating, 401 reviews

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.

Popular amenities for Callicoon outdoor seating rentals

Quick stats about holiday rentals with outdoor seating in Callicoon

  • Total holiday rentals

    Explore 10 holiday rentals in Callicoon

  • Nightly prices starting at

    Callicoon holiday rentals start at $267 AUD per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Callicoon holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Callicoon rentals

  • 5 Average rating

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