House vacation rentals in Callicoon

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Top-rated house rentals in Callicoon

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Guest favorite
A spacious green lawn is bordered by trees displaying vibrant autumn colors. The house, featuring a large deck, is positioned to offer scenic views of the surrounding landscape. Gray skies cast a soft light over the area, enhancing the natural beauty.
Home in Callicoon
4.92 out of 5 average rating, 119 reviews

Cozy Catskills Escape with Wildlife and Views

Welcome to Deer Hollow, a bucolic retreat sitting on three lush acres in the Sullivan County Catskills. Deer Hollow is nestled on a hill, just a five minute drive to the hamlet of Callicoon on the Delaware River. Only a two hour drive from New York City's George Washington Bridge, Callicoon is a charming community, waiting to be explored. With four bedrooms and two full baths, Deer Hollow comfortably sleeps up to eight guests, making it the perfect gathering place for your family and friends.

Top guest favorite
Home in Equinunk
5 out of 5 average rating, 211 reviews

Art House Bird Sanctuary at EBC Sculpture Park

The Art House is set in a Sculpture Park developed by the artists Tom and Carol Holmes.The Parks 38 acres of rolling hills, grass land with valley views are bordered by two streams and woodlands.The views are magnificent.The house is set on the second tier of three rolling hills.Tom creates magical and life changing experiences in the landscape; at EBC Bird Sanctuary Sculpture Park. The Art House offers exceptional privacy, incredible quiet and extensive wildlife. A pristine experience awaits.

Guest favorite
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
4.99 out of 5 average rating, 234 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 favorite
A modern home with large windows is set against a backdrop of trees. A spacious deck features outdoor furniture, including a table with an umbrella for shade and two red chairs. String lights provide gentle illumination, enhancing the outdoor space.
Home in Narrowsburg
5 out of 5 average rating, 155 reviews

Ridge Haven: Catskills home w/ open deck & firepit

Welcome to Ridge Haven! Our home features an open floor plan w/ a fireplace, a big deck w/ grill, a seasonal outdoor shower & a fire pit on the upper lawn. Propane & firewood included. Only 2 hours from NYC in the hamlet of Narrowsburg. Nestled against the Delaware River, it is home to a variety of shops, acclaimed restaurants, art galleries, & antique stores. <15 mins from hikes, swimming/tubing on the Delaware, Bethel Woods, and Callicoon. <30-60 mins to skiing (Elk, Big Bear & Shawnee).

Top guest favorite
A spacious deck is equipped with several Adirondack chairs, overlooking a tranquil lake surrounded by bare trees. The view highlights the calm water and gentle natural landscape, inviting relaxation in an outdoor setting.
Home in Jeffersonville
4.96 out of 5 average rating, 125 reviews

The Nest At Swiss - Lakefront In The Catskills

Modern, classic, luxurious, and comfortable. Lakefront four bedroom (1 K, 2 Q, trundle with 2 singles) with epic year round environment and beautiful nature and lake views from almost everywhere. Wrap around deck on main level accompanied by decks on all three of the upstairs bedrooms. All new kitchen, Bathrooms, and basement with movie theater. Hot tub, fire pit, dock on lake for swimming and fishing. Outdoor dining on main deck with grill. Lush private feel without being too far from town.

Top guest favorite
Home in Napanoch
4.94 out of 5 average rating, 223 reviews

Stunning Passive Solar Cabin on 135 acres & pond

Just the perfect cabin. This newly built, passive solar house has a wood-burning stove, incredible views and is drenched with light. The house is intimate yet connected to the outside, with total seclusion and every imaginable modern convenience! It’s an architect-designed marvel of concrete, glass and reclaimed wood that sits on 135 acres of field and forest with a lovely swimming pond and miles of hiking trails. The cabin sleeps up to 6 people in two bedrooms and a spacious sleeping loft.

Guest favorite
Home in Livingston Manor
4.92 out of 5 average rating, 169 reviews

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.

Top guest favorite
Home in Narrowsburg
4.92 out of 5 average rating, 478 reviews

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

Top guest favorite
A snow-covered deck showcases a scenic view of rolling hills and a forest in the distance. Snow blankets the ground, with trees dusted in white. Bright sunlight illuminates the landscape, creating a serene winter atmosphere.
Home in Jeffersonville
4.96 out of 5 average rating, 132 reviews

Private, Elegant Chalet w/ A Breathtaking View

Welcome to your all-season escape, to this funky yet luxury, spacious yet cozy, modern yet classic chalet. Where you can experience the perfect vacation, whether it is outdoors with family and friends or appreciating the art pieces throughout the interior. Greet the evenings with a cozy wood-stove and a movie or a glass of wine and a book, sunset with drinks on the deck and the mornings with a fresh espresso. Make some memories at this unique and family-friendly place.

Guest favorite
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, 192 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 favorite
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, 192 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 favorite
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
4.96 out of 5 average rating, 104 reviews

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.

Popular amenities for Callicoon house rentals

Quick stats about house rentals in Callicoon

  • Nightly prices starting at

    Callicoon vacation rentals start at G$41,814 GYD per night before taxes and fees

  • Verified guest reviews

    Over 330 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Callicoon rentals

  • 4.9 Average rating

    Callicoon stays are highly rated by guests—averaging 4.9 out of 5!

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