House holiday rentals in Southold

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

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.

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.

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, and lots more.

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom and a second bathroom as part of an open primary suite. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Sorry but, absolutely no animals as owner has severe allergy.

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.