Holiday houses in Southold

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Top-rated holiday rentals in Southold

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Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

11–18 Jan

$1,298 NZD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 14 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.

25 Mar – 1 Apr

$411 NZD per night

Guest favourite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

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

7–14 Oct

$573 NZD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 19 reviews

Horton House

Hello and thank you for taking a look at Horton House, one of the oldest homes in the state of New York! This home, originally built in 1653, has been beautifully restored and renovated. It features a well-equipped kitchen, colorful gardens and plenty of room to entertain. The Hampton Jitney and the Long Island Railroad are no more than a five-minute walk from the house along with village shops, restaurants and markets. A wonderful place to spend the winter holiday! Southold permit #0932

28 Dec – 4 Jan

$554 NZD per night

Guest favourite

Apartment in Southold

4.96 out of 5 average rating, 100 reviews

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!

31 Aug – 7 Sep

$515 NZD per night

Superhost

Cottage in Southold

4.89 out of 5 average rating, 19 reviews

Quaint Cottage Close to LI Sound

This recently renovated cottage is close to everything, making it easy to plan your visit to the beautiful North Fork, located in the middle of wine country and close to the Long Island Sound. The property is perfectly located in the middle of Southold Town and a short drive from Greenport Village allowing you the opportunity to explore all that the North Fork has to offer. Antique shops, art galleries, beaches, biking, hiking, restaurants, vineyards and our local farm stands.

9–16 Feb

$582 NZD per night

Guest favourite

Guest suite in Greenport

4.92 out of 5 average rating, 276 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

1–8 Jun

$548 NZD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 9 reviews

Gorgeous home with heated gunnite pool!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

23–30 Nov

$850 NZD per night

Guest favourite

Guest suite in Southold

4.94 out of 5 average rating, 97 reviews

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.

28 Dec – 4 Jan

$418 NZD per night

Guest favourite

Home in Southold

4.96 out of 5 average rating, 26 reviews

Bright Oasis in Beautiful North Fork Wine Country

Enjoy this idyllic family friendly home in the heart of North Fork, Long Island. It's a newly renovated and spacious 4 bedroom and 2 bath home. The open first floor plan leads to an equally as spacious and enjoyable back yard. From the private backyard, you can launch your paddle board, kayak (we have 2 for guests to use) or boat right off the dock to enjoy the peace and tranquil Goose Creek, or walk a few minutes down the road to Croteau Winery.

22–29 Jan

$1,091 NZD per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

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.

23–30 Mar

$1,527 NZD per night

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 220 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!

20–27 Aug

$999 NZD per night