Family-friendly vacation rentals in Orient

Greenport Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable. Please note this rental may not suitable for small children due to the staircase. A new baby gate has been installed at the top of the stairs. Village of Greenport Short Term Rental Permit #R26-021.

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.

Hay Beach Family Home: Fire Pit, Playroom, Yard

Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Harbor Heights

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 is for rental of 2nd floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

1830 Historic garden wing - walk to it all

This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

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!

Private Suite in a Greenport Historical Townhouse

Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.