Vacation rentals in Southold

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.

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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!

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!

Private Loft-Walk to Town/Beach/Train/Wine/Jitney

Relax in this freshly renovated, light-filled, fully appointed garden loft. Centrally located off Main street on a quiet private road, you are minutes walk to the beach, 5 star Michelin restaurants, the North Fork wine trail, downtown shops, farm stands and more! On the North Fork wine trail and minutes to the Southold train and jitney stops--the location is convenient to it all and just minutes drive to Greenport village as well. And, you will have the entire space!

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).

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. Less than 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, and Love Lane.

North Fork paradise between beaches and vineyards

Kick back and relax in this calm, stylish retreat. Nestled between vineyards and farmlands, this newly renovated mid-century ranch with a beautiful 14x50' heated salt water pool is a short hop to beautiful beaches, wineries, restaurants, and farm stands. Enjoy nature in a secluded park-like setting and explore everything the NoFo has to offer all year around. Please note that there are no parties, gatherings or unannounced guests allowed.

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.