Southold vacation rentals

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Top-rated vacation rentals in Southold

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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.

Mar 24 – 31

$650 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

May 12 – 19

$205 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!

Sep 21 – 28

$225 per night

Popular amenities for Southold vacation rentals

Stay near Southold's top sights

Pindar Vineyards41 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
Greenport Harbor Brewery and Restaurant54 locals recommend

Other great vacation rentals in Southold

Guest favorite

Home in Southold

5.0 out of 5 average rating, 14 reviews

Le Petit Cottage Southold NY

Dec 8 – 15

$215 per night
Guest favorite

Guesthouse in Southold

4.95 out of 5 average rating, 39 reviews

Southold- Adorable 1 Bedroom Cottage

Apr 6 – 13

$221 per night
Guest favorite

Home in Southold

5.0 out of 5 average rating, 17 reviews

Horton House

Nov 17 – 24

$266 per night
Guest favorite

Cottage in Southold

4.94 out of 5 average rating, 32 reviews

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

Sep 5 – 12

$335 per night
Guest favorite

Cottage in Southold

4.95 out of 5 average rating, 21 reviews

Adorable Cottage

Dec 11 – 18

$324 per night
Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 72 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Aug 30 – Sep 6

$260 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 18 – 25

$149 per night
Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Apr 25 – May 2

$474 per night
Guest favorite

Home in Southold

4.94 out of 5 average rating, 18 reviews

NEW LISTING: COMPLETELY RENOVATED 4-BED, 3-BATH

Apr 2 – 9

$409 per night
Guest favorite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house ~ Fireplace ~ North Fork Wineries

May 28 – Jun 4

$656 per night
Guest favorite

Home in Greenport

5.0 out of 5 average rating, 32 reviews

Beachfront Greenport Villa

Jan 21 – 28

$517 per night
Guest favorite

Home in Southold

4.96 out of 5 average rating, 26 reviews

Bright Oasis in Beautiful North Fork Wine Country

Mar 11 – 18

$504 per night

Other great vacation rentals in Southold

Superhost

Cottage in Southold

4.89 out of 5 average rating, 18 reviews

Quaint Cottage Close to LI Sound

Sep 19 – 26

$275 per night
Guest favorite

Home in Southold

5.0 out of 5 average rating, 32 reviews

Southold Comfort - North Fork Getaway

Jul 9 – 16

$611 per night
Guest favorite

Loft in Southold

5.0 out of 5 average rating, 11 reviews

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

Mar 12 – 19

$207 per night
Guest favorite

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

Dec 2 – 9

$499 per night
Guest favorite

Home in Cutchogue

4.96 out of 5 average rating, 24 reviews

North Fork Estate in Midst of Vinyard

May 1 – 8

$626 per night
Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Nov 11 – 18

$570 per night
Guest favorite

Home in Southold

4.97 out of 5 average rating, 35 reviews

Water & Vineyard views, 4 bedrooms

Nov 9 – 16

$900 per night
Guest favorite

Home in Peconic

5.0 out of 5 average rating, 11 reviews

Coastal Cottage on the Water

Apr 19 – 26

$395 per night
Superhost

Apartment in Greenport

4.78 out of 5 average rating, 46 reviews

2 Bedroom Greenport Waterfront Coastal Cottage

Dec 23 – 30

$499 per night
Guest favorite

Home in Greenport

4.96 out of 5 average rating, 24 reviews

Water front 3 bedrooms 2 bathrooms beach house

Oct 19 – 26

$838 per night
Guest favorite

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

May 13 – 20

$415 per night
Guest favorite

Home in Cutchogue

5.0 out of 5 average rating, 17 reviews

North Fork Escape Heated Pool Beach & Wineries

Apr 7 – 14

$309 per night

Quick stats about vacation rentals in Southold

Total rentals

210 properties

Rentals with a pool

60 properties have a pool

Pet-friendly rentals

80 properties allow pets

Family-friendly rentals

180 properties are a good fit for families

Total number of reviews

2.7K reviews

Nightly prices starting at

$90 before taxes and fees

Frequently Asked Questions

  • 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.

  • Are there Southold house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 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 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.

  • 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 160 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 20 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 50 homes with self check-in, over 160 homes with wifi, over 90 homes with a bbq area, over 20 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Southold?

    Yes! Work meets play with ease at over 110 vacation rentals in Southold featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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  2. United States
  3. New York
  4. Suffolk County
  5. Southold