Vacation rentals in Callicoon

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Top-rated vacation rentals in Callicoon

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Guest favorite
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, 246 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)

Guest favorite
A private deck area features a wooden chair beside a neatly stacked pile of firewood. The entrance displays a large sliding glass door, illuminated from within, revealing a warm interior. Soft outdoor lighting complements the natural surroundings of greenery.
Tiny home in Livingston Manor
4.97 out of 5 average rating, 167 reviews

Element House - Off Grid Hideout

Unwind and reconnect with nature in this rustic and comfortable retreat nestled at the edge of a blueberry field. Surrounded by serene Catskills countryside, you’ll feel a world away, yet still be just minutes from outdoor activities, a thriving food scene, and Bethel Woods just 35 min away. Inside, you’ll stay cool with AC, a cozy queen bed, kitchenette, dining table, reliable wifi, and full bath. Outside, relax by the fire pit or cook on the charcoal grill. We are an LGBTQ+ inclusive space.

Top guest favorite
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, 219 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 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 Jeffersonville
4.99 out of 5 average rating, 248 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!

Guest favorite
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 favorite
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, 425 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 favorite
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
4.97 out of 5 average rating, 127 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 favorite
Home in Narrowsburg
4.94 out of 5 average rating, 231 reviews

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

A modern 3BR/2BA Catskills retreat on 6 private acres with a hot-tub, and fireplace. Perched on a hill, this single-level home offers serenity, scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Fireplace Hot Tub Spa Mini Ping-Pong Dart Board High-speed Wi-Fi Narrowsburg Offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

Top guest favorite
Home in Narrowsburg
4.92 out of 5 average rating, 485 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
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.

Guest favorite
A serene lake house is nestled among tall trees beside a calm body of water. A grassy area extends from the house towards the lakeside, with outdoor seating arranged on the lawn. The home features large windows, inviting natural light into the living space.
Home in Swan Lake
4.89 out of 5 average rating, 488 reviews

In the clouds your cozy- lake house

Cozy lake house in Catskill,only 2 hrs away from NYC.The property has 2 Bedroom 1-1/2 baths & sleeps 4-6 people. Guest can enjoy kayaking fishing in property.The property is close proximity 2 downtown Jeffersonville & Bethel-Woods Center for Arts (Historic Site of the 1969 Woodstock Music & Art Fair).Nearby attractions ~ Villa Roma Resorts,Resort World Casino, Kartrite Resort & Water park & Holiday Mountain Ski resort.Visit local farms and Catskill brewery

Top guest favorite
A serene cabin is situated next to a tranquil pond, reflecting the surrounding greenery. The dock extends into the water, offering a peaceful outdoor space. The area features a well-maintained lawn with tall grasses, enhancing the natural setting.
Cabin in Callicoon
4.99 out of 5 average rating, 213 reviews

The Cabin at Pleasant Valley Farm

The cabin is located on a dirt road on our farm with a beautiful pond and an amazing view! This off-grid, cabin has two queen beds (100% cotton sheets), a mini-kitchen with a battery-ignition gas range, solar powered refrigerator, solar lighting, a wood stove, an outdoor shower, a fire pit, and an old-fashioned outhouse. An expansive porch and dock provide comfortable outdoor living. A seasonal favorite, the cabin is available May-Oct.

Popular amenities for Callicoon vacation rentals

Quick stats about vacation rentals in Callicoon

  • Total vacation rentals

    Explore 20 vacation rentals in Callicoon

  • Nightly prices starting at

    Callicoon vacation rentals start at € 164 per night before taxes and fees

  • Verified guest reviews

    Over 420 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Callicoon vacation rentals include wi-fi access

  • 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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  3. New York
  4. Sullivan County
  5. Callicoon