Holiday houses 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

Family · Location · Air conditioning

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Family · Location · Kitchen

Kenney's Beach Loft - Vineyards, Horton Lighthouse

Kenny’s Beach Loft is a cozy, pet-friendly open-concept queen bed studio with 1 bathroom, a kitchenette, comfortable living and dining area, in-unit washer and dryer, and a private patio. Perfect for families and couples getaway. Just steps from Kenney’s Beach for stunning sunsets and peaceful walks. Minutes to Southold Fish Market, Croteaux Vineyards, Horton Point Lighthouse, and North Fork wineries for dining, wine tasting, and exploring. Enjoy coastal charm, seaside air, and total serenity.

Value · Location · Kitchen

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!

Value · Location · View

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.

Location · Family · Solo travel

Wine Country Home

Escape to the heart of Long Island’s Wine Country at our cozy, thoughtfully designed retreat. Surrounded by vineyards, farms, and picturesque countryside, our home offers the perfect blend of relaxation and adventure. Sip your way through nearby wineries, stroll local beaches, or enjoy North Fork shops and restaurants—all just minutes away. Whether you're here for a romantic getaway or weekend with friends/family, our home provides an ideal base for everything this lovely region offers.

Value · Location · Walkability

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!

Value · Location · Access

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 🌊

Family · Value · View

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.

Family · Location · Amenities

Southold Sea'renity

Kick back and enjoy the peaceful surroundings of this beautiful 3-bedroom, 2-bathroom house. Outdoor oasis with hot tub, BBQ, shower, brand new deck & kayaks. Steps away from a fishing lake & 6 houses away from Kenny's beach. This house has been completely remodeled & is perfectly located to fit your getaway needs. Master Bedroom- queen bed, full bath Bedroom 2&3- queen beds Pull out couch and some other extras. Towels, bed sheets, soap, toilet paper, and pillows are included

Family · Value · TV

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.

Location · Value · TV

Adorable Cottage

Kick back and relax in this calm, stylish space. Lounge on the spacious front porch or the enormous, fenced in yard. Bring your pup! Come enjoy all the Northfork has to offer…vineyards, farms, beaches, charming Towns all within walking/biking distance from the cottage. Fully stocked with bedroom linens, bathroom linens, chef’s kitchen…just pack your clothes, we have everything you need.

Value · Family · Access