Holiday rentals 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.

14–21 Jan

$1,015 SGD per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 74 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. Home was designed by well known home and garden designer, Conni Cross. 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.

18–25 Oct

$426 SGD 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.

26 Feb – 5 Mar

$305 SGD per night

Guest favourite

Apartment 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

27 Apr – 4 May

$312 SGD per night

Guest favourite

Cottage in Southold

4.94 out of 5 average rating, 32 reviews

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!

10–17 Feb

$693 SGD per night

Guest favourite

Flat 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!

26 Aug – 2 Sep

$399 SGD 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.

27 Jan – 3 Feb

$430 SGD 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!

9–16 Mar

$328 SGD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 302 reviews

The Sandpiper- Apt #1

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).

15–22 Dec

$190 SGD 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!

3–10 Mar

$635 SGD 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.

13–20 Jan

$326 SGD 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.

12–19 Nov

$611 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Southold holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Southold's top sights

Pindar Vineyards41 locals recommend

Croteaux Vineyards70 locals recommend

Horton Point Lighthouse Nautical Museum31 locals recommend

Sparkling Pointe Vineyards & Winery64 locals recommend

The Halyard Restaurant32 locals recommend

A Lure Chowder House & Oysteria27 locals recommend

Other great holiday rentals in Southold

Guest favourite

Home in Southold

5.0 out of 5 average rating, 31 reviews

Salt & Sea House - Near wineries, farms, & beaches

3–10 Sep

$660 SGD per night

Guest favourite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

11–18 Jun

$997 SGD per night

Guest favourite

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

21–28 Oct

$779 SGD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

28 Oct – 4 Nov

$766 SGD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 35 reviews

Beachfront Greenport Villa

3–10 Nov

$1,059 SGD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 25 reviews

Greenport walk to beach & vineyard! Brand new home

27 Aug – 3 Sep

$1,088 SGD per night

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

30 Jul – 6 Aug

$1,264 SGD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 32 reviews

Southold Comfort - North Fork Getaway

23–30 Jul

$959 SGD per night

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Quick stats about holiday rentals in Southold

Total rentals	220 properties
Rentals with a pool	60 properties have a pool
Pet-friendly rentals	80 properties allow pets
Family-friendly rentals	190 properties are a good fit for families
Total number of reviews	2.7K reviews
Nightly prices starting at	$136 SGD before taxes and fees

Holiday rentals in Southold

Top-rated holiday rentals in Southold

Cottage in Riverhead

Home in Cutchogue

Home in Southold

Apartment in Greenport

Cottage in Southold

Flat in Southold

Cottage in Southold

Guest suite in Greenport

Home in Greenport

Home in Southold

Guest suite in Southold

Home in Southold

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Southold holiday rentals

Stay near Southold's top sights

Other great holiday rentals in Southold

Home in Southold

Home in Southold

Home in Southold

Home in Greenport

Home in Greenport

Home in Southold

Cottage in Greenport

Home in Southold

Quick stats about holiday rentals in Southold

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore