Southold vacation rentals

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Top-rated vacation rentals in Southold

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Guest favorite

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.

Oct 1 – 8

G$155,579 GYD per night

Guest favorite

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.

Feb 16 – 23

G$45,517 GYD per night

Guest favorite

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

Oct 7 – 14

G$66,881 GYD per night

Guest favorite

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!

Aug 31 – Sep 7

G$61,124 GYD per night

Guest favorite

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!

Feb 22 – Mar 1

G$50,322 GYD per night

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - 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).

Dec 5 – 12

G$29,047 GYD per night

Guest favorite

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!

Feb 27 – Mar 6

G$97,300 GYD per night

Guest favorite

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.

Mar 22 – 29

G$32,392 GYD per night

Guest favorite

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

Feb 2 – 9

G$81,681 GYD per night

Guest favorite

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.

Mar 26 – Apr 2

G$173,400 GYD per night

Guest favorite

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!

Aug 20 – 27

G$119,078 GYD per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 585 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Aug 26 – Sep 2

G$41,667 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Southold vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Southold

Superhost

Cottage in Southold

4.89 out of 5 average rating, 19 reviews

Quaint Cottage Close to LI Sound

Mar 9 – 16

G$65,934 GYD per night

Guest favorite

Cottage in Southold

4.95 out of 5 average rating, 21 reviews

Adorable Cottage

Nov 10 – 17

G$88,805 GYD per night

Guest favorite

Home in Southold

5.0 out of 5 average rating, 31 reviews

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

Oct 8 – 15

G$68,865 GYD per night

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 74 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Dec 17 – 24

G$66,644 GYD per night

Guest favorite

Home in Southold

4.96 out of 5 average rating, 26 reviews

Bright Oasis in Beautiful North Fork Wine Country

Dec 10 – 17

G$89,437 GYD per night

Guest favorite

Cottage in Southold

4.94 out of 5 average rating, 32 reviews

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

Jun 3 – 10

G$93,977 GYD per night

Guest favorite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Jun 11 – 18

G$137,594 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 35 reviews

Beachfront Greenport Villa

Mar 15 – 22

G$124,107 GYD per night

Show all

Other great vacation rentals in Southold

Guest favorite

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

Oct 25 – Nov 1

G$119,373 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Oct 20 – 27

G$136,614 GYD per night

Guest favorite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Mar 11 – 18

G$98,345 GYD per night

Guest favorite

Guest suite in Cutchogue

4.9 out of 5 average rating, 83 reviews

Enjoy a relaxing getaway to the North Fork

Sep 1 – 8

G$43,419 GYD per night

Guest favorite

Home in Greenport

4.96 out of 5 average rating, 25 reviews

Water front 3 bedrooms 2 bathrooms beach house

Nov 17 – 24

G$160,638 GYD per night

Superhost

Apartment in Greenport

4.78 out of 5 average rating, 46 reviews

2 Bedroom Greenport Waterfront Coastal Cottage

Aug 30 – Sep 6

G$133,277 GYD per night

Guest favorite

Loft in Southold

5.0 out of 5 average rating, 12 reviews

Entire Loft-Walk to Town, Beach, Train, Wine Trail

Jan 29 – Feb 5

G$49,258 GYD per night

Guest favorite

Home in Peconic

5.0 out of 5 average rating, 11 reviews

Coastal Cottage on the Water

Oct 17 – 24

G$118,757 GYD per night

Show all

Quick stats about vacation 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
G$20,889 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southold?
Yes! Work meets play with ease at over 120 vacation rentals in Southold featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Southold?
Four-legged friends are welcome in Southold. Choose from more than 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Southold?
Experience the best of Southold with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Southold house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 house rentals with pools in Southold, available on Airbnb. Make a splash and soak up the sun in style!
Do cottage rentals in Southold have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have self check-in?
Absolutely! We offer over 50 house rentals with self check-in in Southold. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Southold have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have a gym?
Absolutely! We offer over 30 house rentals with a gym in Southold. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Southold?
Southold has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cottage Rentals in Southold?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Southold vacation rentals

Top-rated vacation rentals in Southold

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Southold vacation rentals

Stay near Southold's top sights

Other great vacation rentals in Southold

Cottage in Southold

Cottage in Southold

Home in Southold

Home in Cutchogue

Home in Southold

Cottage in Southold

Home in Southold

Home in Greenport

Other great vacation rentals in Southold

Home in Southold

Home in Greenport

Home in Mattituck

Guest suite in Cutchogue

Home in Greenport

Apartment in Greenport

Loft in Southold

Home in Peconic

Quick stats about vacation rentals in Southold

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southold?

Are there pet-friendly vacation rentals in Southold?

How much does it cost to stay in cottage rentals in Southold?

Are there Southold house rentals on Airbnb with pools?

Do cottage rentals in Southold have a bbq area?

Do house rentals in Southold have self check-in?

Do cottage rentals in Southold have wifi?

Do house rentals in Southold have a gym?

Are there family-friendly cottage rentals in Southold?

What are the most popular amenities for Cottage Rentals in Southold?

Destinations to explore