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.

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!

Guest favorite

Guest suite in Greenport

4.92 out of 5 average rating, 277 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!

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

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).

Guest favorite

Home in Southold

5.0 out of 5 average rating, 11 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!

Guest favorite

Guest suite in Southold

4.94 out of 5 average rating, 99 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.

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

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.

Guest favorite

Home in Greenport

4.97 out of 5 average rating, 223 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!

Guest favorite

Townhouse in Greenport

4.96 out of 5 average rating, 100 reviews

Northfork Townhouse-walk to all/Newly Renovated

Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitchen, bathrooms & bedrooms. Enjoy all the North Fork has to offer: wineries, breweries, amazing restaurants, shops and beaches! 3 Bedrooms 1.5 bathrooms. We welcome you to come stay in our beautiful home and take in all the beauty of the North Fork. You can park your car and not have to drive again till you leave!

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 587 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!

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 145 reviews

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.

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 165 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

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

The Halyard Restaurant32 locals recommend

Sparkling Pointe Vineyards & Winery64 locals recommend

A Lure Chowder House & Oysteria27 locals recommend

Other great vacation rentals in Southold

Guest favorite

Home in Southold

5.0 out of 5 average rating, 18 reviews

Le Petit Cottage Southold NY

Guest favorite

Cottage in Southold

4.9 out of 5 average rating, 20 reviews

Quaint Cottage Close to LI Sound

Guest favorite

Guest suite in Cutchogue

4.9 out of 5 average rating, 83 reviews

Enjoy a relaxing getaway to the North Fork

Guest favorite

Cottage in Southold

4.94 out of 5 average rating, 32 reviews

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

Guest favorite

Cottage in Southold

4.95 out of 5 average rating, 21 reviews

Adorable Cottage

Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 76 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Guest favorite

Home in Southold

4.92 out of 5 average rating, 13 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Guest favorite

Home in Southold

5.0 out of 5 average rating, 31 reviews

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

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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

Guest favorite

Home in Southold

5.0 out of 5 average rating, 32 reviews

Southold Comfort - North Fork Getaway

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Guest favorite

Home in Cutchogue

5.0 out of 5 average rating, 25 reviews

North Fork paradise between beaches and vineyards

Guest favorite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Superhost

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

Charming Home W/ Beach & Dock Access

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

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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
$100 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 house rentals in Southold?
Experience the best of Southold with our house 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.
Do house rentals in Southold have a bbq area?
Absolutely! We offer over 90 house rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.
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 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 house rentals in Southold have wifi?
Absolutely! We offer over 170 house 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 house rentals in Southold?
Southold has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Southold?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a gym, over 90 homes with a bbq area, over 170 homes with wifi, over 50 homes with self check-in, 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

Home in Southold

Cottage in Southold

Guest suite in Cutchogue

Cottage in Southold

Cottage in Southold

Home in Cutchogue

Home in Southold

Home in Southold

Other great vacation rentals in Southold

Home in Southold

Home in Southold

Home in Greenport

Home in Cutchogue

Home in Mattituck

Home in Greenport

Home in Greenport

Cottage in Greenport

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 house rentals in Southold?

Do house rentals in Southold have a bbq area?

Are there Southold house rentals on Airbnb with pools?

Do house rentals in Southold have self check-in?

Do house rentals in Southold have wifi?

Do house rentals in Southold have a gym?

Are there family-friendly house rentals in Southold?

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

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