Tiny house holiday rentals in Long Island

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)

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Montauk Oceanview

Wake up to ocean vistas every morning in a charming cottage. There are stunning views of the waves, soothing ocean sounds, and a gentle sea breeze. Sip coffee on a sun-drenched porch, enjoy a sunset stroll along sandy beaches, or simply unwind with the mesmerizing horizon as your backdrop, this cottage provides the perfect blend of comfort and charm. The cottage features a cozy interior with a working fireplace, modern amenities, and large windows that showcase the stunning seaside scenery.

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

The Oasis Tiny House

This Custom Built Modern Tiny House Is Private And Cozy. Our Location In Centereach Long Island, NY Is Just That...In The Center Of Long Island So Whether You Want to Visit The Local Beaches Or Treat Yourself To Some Well Deserved Shopping This Location Has It All, Museums, Shopping Malls, Tanger Outlets, Wine Country, The Hamptons, And New York City Are All Close By. It Is Also Conveniently Located Just A Few Miles From SUNY Stony Brook If You’re Planning To Visit The College

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Captain's Cottage on Working Farm with Animals

Charming, fully renovated cottage with cathedral ceilings and private deck. Home has a separate queen bedroom, kitchen and living room on the main floor with small stove fireplace. There is a small loft on the 2nd floor with 2 twin beds accessed by a library ladder (note: no standing headroom in loft). Private outdoor deck with seating and BBQ. Fast wi-fi, laundry access and pet friendly.

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.