Family-friendly holiday rentals in Long Island Sound

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

Andes Valley View

This home is a beautiful mix of cozy and modern. You’ll love cooking in the kitchen and taking in the view from the second story deck. The property is stunning, with wide meadows and dense woods. There are 140 acres to explore and utilize for events like weddings or a retreats. There is a half acre pond with a pond house at the top of the property and a trout stream running along the bottom. It’s everything you could hope for in a Catskills getaway, all nestled overlooking the town of Andes.

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Birdhouse: A Starry Escape in the Catskills

The Birdhouse at Bellfire in Catskills located on a bucolic property in the Catskills Mountains surrounded by maple forest, wildflowers field, and miles to roam. The cabin features a 6 ft skylight above the bedroom, an ode to the awe-inspiring skies of the Meeker Hollow, one of the best spots for stargazing in NY state, and an 11ft-tall window wall in the living space, framing the sprawling, lush landscape. Off-grid & unplugged—see full details before you book.

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers that is sold at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, and chickens. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109