House holiday rentals in Delaware

Swimming Hole, OMG Game Barn! Hot Tub

10% discount on 3 night stays! Swimming hole in Callicoon Creek + 3,500 sq ft OMG Barn with 3 floors of fun: games, lounge, playground, billiards...! Stunning water views year-round. Excellent trout fishing. Two creeks on the property! Cross one creek into a 7 acre forest oasis. FAST WiFi, Hot Tub, Firepit, grill, Deck. Callicoon has shops, restaurants and Delaware River access. Seminary Hill 5 min. Villa Roma 9 min (skiing, tubing). We're renovated, clean and stocked with a barn like no other!

Treetop deck, hot tub, and chef's kitchen

Welcome to our spacious, pet-friendly 1960s home tucked away on 5.5 private acres - just mins from two of the most popular towns in the Sullivan Catskills: Roscoe and Livingston. This bright 4 bed/3 ½ bath home works great for a couple or a crowd with plenty of indoor and outdoor space to gather or spread out. There’s a dreamy (and VERY well-stocked) kitchen. Two living rooms are perfect for leisure or work-from-home needs, and the home is stocked for visiting families. Deluxe 6-person hot tub!

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

Hobbit House in Callicoon on Farmland

Experience Americana. 2 hours from NYC in Catskill Mountains. Secluded, cozy hideaway on acres of private land. Extremely peaceful and private and in the middle of nature. It's a hobbit house - half is built into the land. Because of the design, it stays cool in summer and warm in winter. Have a few acres so you can run around naked and feel true freedom. Have strong WIFI, very clean water, comfy bed. Go skeet shooting, visit farms, go fly fishing. Live like Thoreau, but with comfort.

Woodsy Retreat, Sunny Home with Paths and Stream

This lovely hand-made home in the woods, lined with windows, flooded with light, has 2 bedrooms and 2 full baths, and a large wraparound deck facing a feisty stream. It has 10 hilly acres of woods with its own paths to wander. Work, relax and play in its inspiring kitchen and lofty spaces stocked with albums, movies, books, art supplies, and instruments. Enveloped in nature, yet only a 10 minute drive to local hot spots including Narrowsburg, Callicoon, Skinners' Falls and Bethel Woods.

3BR/2BA • Fireplace & Hot Tub Near Bethel Woods

Perched on a hill with fantastic views, this modern 3BR/2BA Catskills retreat is perfect for couples or small groups. Unwind in the hot tub, cozy up by the indoor fireplace, make s'mores by the outdoor fire-pit, or enjoy your evening cocktail by the additional gas fire-pit on the patio. Watch deer wander through the meadow, enjoy a game of ping-pong or darts. House offers stylish interiors and premium bedding. Check out our guide-book for activities in the area.

Bethel Woods Escape: Private Oasis with Hot Tub

Welcome to Bethel Woods Escape - a gorgeous modern home surrounded by woodlands of Eastern pine and hemlock trees. In 1969 Bethel Woods was home to the notorious Woodstock festival. Located in the country hills of the Sullivan Catskills, Bethel Woods is an amazing place to explore, hike, and listen to live music. Just 5 minutes away from Bethel Woods Center of the Arts, you will find a stunning A-Frame home with a private hot tub waiting to host your next adventure.

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.

Modern Secluded Retreat

Escape to the center of 11+ acres of woods, water, and dark starry skies—under 2 hours from NYC. Walls of windows pull the outside in, with a stream, pond, and constant wildlife just beyond. Warm up by the fireplace, unwind in the open living space, and sleep deep in a king bed. A large jetted bathtub, bonus half bath, and a flexible bonus room with pool table and ping pong table on heated floors round it out. Peaceful, private, and made for slowing down.

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.

Creekside Retreat•Fire Pit•Game Room•Dog Friendly

A creekside Catskills retreat for families, friends, and dogs. Spend your days exploring the private creek and swimming hole, and your evenings around the fire pit while the kids enjoy ping pong and shuffleboard. • Private creek & swimming hole • Sleeps 8 • Game room • Fire pit & deck • 10 min to Livingston Manor • Dog friendly

SwissHill Farmhouse| 5 Bedrooms rustic charm

Escape the city and step into 3.5 acres of wooded serenity at this 1900s farmhouse in the heart of the Sullivan Catskills. With room for 9 guests, fire-pit under the stars, and blazing fast wifi, it’s perfect for group getaways, remote work retreats, and family adventures alike.