House holiday rentals in Southold

4.91 out of 5 average rating, 107 reviews

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

4.98 out of 5 average rating, 102 reviews

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, and recently & lovingly fully renovated and restored. 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.

4.98 out of 5 average rating, 49 reviews

Le Petit Cottage, Southold, NY

Experience the charm of a two-bedroom cottage in Southold, New York. Enjoy easy access to nearby South Harbor Park Beach, where you can swim and soak up the sun. Immerse yourself in the local wine scene with wineries just a short distance away. Explore nearby farms to savor fresh produce and artisanal goods. Unwind on the outdoor deck in the fresh North Fork air after a day of swimming, wine tasting and farm visits. Greenport and Shelter Island Ferry are a short ten minute drive away.

4.97 out of 5 average rating, 154 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

5 out of 5 average rating, 62 reviews

Beachfront Greenport Villa

Welcome to Villa Sonore. A gorgeous beachfront villa in Greenport located right on the LI Sound. Walk to restaurants and bars at the Soundview. Bike to North Fork wineries, breweries, farms and town. Or just relax on the enclosed porch or back deck and take in the magnificent views of the beach. Listen to the waves crash and enjoy views of the water that can only be rivaled by being out at sea! Paddle boards, bicycles, beach chairs and an umbrella are provided for our guests. Enjoy!

4.94 out of 5 average rating, 187 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

4.93 out of 5 average rating, 114 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

4.93 out of 5 average rating, 135 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

4.97 out of 5 average rating, 206 reviews

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.

4.97 out of 5 average rating, 260 reviews

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!