Holiday rentals in Orient

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Bayview house with salt water pool & private chef

My bay view house is a little slice of paradise! Steps to Front and Main street its perfectly located to explore Greenports many restaurants and activities. With a fully enclosed and private backyard you and your guests will enjoy a heated salt water pool, brand new outdoor furniture, a fire pit, grill and plenty of shade. Inside I've updated furniture, have all new linens and the beds a super comfy. Celebrating something special? My private chef services are available at an additional cost.

Bungalow by the Bay

SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Bungalow by the Bay is an Inhabitable Work of Art, recrafted by owner architects. The design is inspired by all of the beauty of coastal living, incorporating organic and natural elements and environmentally conscious technology, to create a happy and healthy living space. Bungalow by the Bay is ideal for those who love sunrises, nature, water, fine wine, delicious food and dreamy sunsets.

Charming North Fork escape by the beach

Enjoy a serene retreat on the North Fork, where your stay promises tranquility and convenience. Our home features a sparkling pool (5/15-9/26), an ample backyard, and is just a short stroll from a pristine beach on the LI Sound. Located just 10 minutes from Greenport, you'll have easy access to boutique shops, gourmet dining, and local arts. Whether you're seeking a peaceful getaway or a base to explore the area's rich offerings, this home is the ideal destination for your next escape.

Aqua Vista

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly-renovated 2-family Home! This rental is 2nd floor apartment (only). Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy. Located right in Greenport. Walking distance to all the restaurants, bars, shopping, coffee shops.

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

The Lane House | Private Beach Escape

The Lane House offers the perfect idyllic getaway with a private community beach access you won't need a car for. 12 minutes to Greenport Village, 20 minutes to Peconic Pickleball courts, 3 minutes from Cross Sound Ferry, 2 minutes to Orient Beach State Park, and near many vineyards, farm stands, and countless other attractions.

Beach House in L.I. Wine Country

Time to wine 🍷 down and make your way to the scenic North Fork. A clean and clutter-free beach house awaits. The Navy House is centrally located in a quiet residential enclave, steps away from Norman E. Klipp Marine Park (aka Gull Pond Beach) and a short drive to Greenport’s Historic Village, vineyards and farmstands.

Cosy North Fork Cottage with large backyard

Peaceful cottage with a huge double lot backyard. Park your car and never need to get in it again! Walk into town and walk to beaches! Our home features fire-pit seating area and outdoor heated shower and beach bikes. Enjoy the fabulous restaurants which are right on your doorstep at this charming little cottage.