Family-friendly holiday rentals in Peconic

Greenport walk to beach & vineyard! Brand new home

Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive to the famed Halyard Restaurant. 5 minutes from countless additional wineries and more restaurants and shops. Relax on the oversized back patio or in front of the firepit. Enjoy all the North Fork has to offer including world famous wines and food. Don't forget to save room for the pies! PICTURES OF FULL SIZED BUNK BEDS COMING SHORTLY! Please message me with any questions

Indoor spaces · Family · Walkability

1BR Apartment - Beach Access - Wineries, Vineyards

Escape to the North Fork in this charming studio! Featuring an open-cocenpt plush queen bed, modern bathroom, a kitchenette with a living and dining area, it’s the perfect solo or couple's retreat. Enjoy the sun in our shared outdoor space. Steps from Kenney’s & McCabe’s Beach for epic sunsets. Minutes from Horton Point Lighthouse. Explore world-class wineries like Sparkling Pointe and Croteaux, local farm stands, and Greenport village. Your idyllic coastal and romantic vineyard getaway awaits!

Kitchen · Indoor spaces · Bathroom

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Kitchen · Family · Comfort

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

French farmhouse-meets-beach house! Stay in a piece of history, set on a farm and down the street from beautiful McCabe’s beach. Originally built in 1763, this charming cape cod was gut renovated in late 2020, and was recently featured in North Forker Magazine’s April issue on historic renos! Farmhouse kitchen with original wood beams is stocked with upscale cookware, allowing you to make the most of the local farm stands, fresh seafood, and wineries. New central AC. No detail was spared!

Indoor spaces · Kitchen · Air conditioning

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact and provide a quiet and comfortable stay. About a five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard.

Family · Kitchen · Quiet

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Indoor spaces · Kitchen · Hiking

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

Indoor spaces · Family · Laundry

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

Indoor spaces · Family · Walkability

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

Kitchen · Indoor spaces · Comfort

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Family · Kitchen · Layout

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Indoor spaces · Kitchen · Location

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Kitchen · Family · Quiet