Choose from 166 vacation rentals located in Southold, New York. Top filters in Southold include Internet / Wifi, Air conditioner, and Kitchen or Kitchenette. Prices range from $83 to $3,057 per night. Our most popular vacation rental types near Southold are Apartment and Hotel.

Top vacation rentals in Southold

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Outdoor spa tub
9.9 / 10.0
Outstanding(169 Ratings)
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
House
 in Southold
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette

Nestled in Southold, this House is perfect for your next vacation. Enjoy Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
9.2 / 10.0
Outstanding(34 Ratings)
A Walk in the Woods Bed and Breakfast
Bed and Breakfast
 in Southold
1 queen bed
Garden · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Southold, at $303 per night for your next great vacation.

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Property view
8.2 / 10.0
Excellent(14 Ratings)
Historic White Blossom House
Inn
 in Southold
Garden · Pets allowed · Kitchen or Kitchenette

This Inn in Southold, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

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Beachfront
View (from property/room)
8.1 / 10.0
Excellent(241 Ratings)
Sound View Greenport
Hotel
 in Greenport
3star
1 sofa bed, 1 queen bed
Pool · Pets allowed · Kitchen or Kitchenette

Experience the best of Southold with this Hotel available for $165. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Vacation rentals with internet & wifi in Southold

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Outdoor dining
9.7 / 10.0
Outstanding(126 Ratings)
Quaint Cottage Close to LI Sound
Cottage
 in Peconic
3 guests · 2 bedrooms · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This Cottage in Southold, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property building
9.0 / 10.0
Excellent(74 Ratings)
The Shoals Suites & Slips
Hotel
 in Southold
4star
1 king bed
Garden · Kitchen or Kitchenette · Air conditioner

Discover the beauty of Southold with a stay at The Shoals Suites & Slips, a top rated Hotel with amenities such as Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Fridge, microwave, oven, stovetop
9.9 / 10.0
Outstanding(71 Ratings)
Private Coastal Two Bedroom Cottage on the Water
Cottage
 in Peconic
6 guests · 4 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Southold? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Living room, Dining area, Evening entertainment
10.0 / 10.0
Outstanding(1 Rating)
Bright Oasis in Beautiful North Fork Wine Country
House
 in Southold
Garden · Pets allowed · Kitchen or Kitchenette

Discover the beauty of Southold with a stay at Bright Oasis in Beautiful North Fork Wine Country, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Southold

Southold travel guide

Let us help you plan your perfect Southold vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Southold, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Southold?

  • Internet / Wifi
  • Air conditioner
  • Kitchen or Kitchenette

What is the price range for rentals in Southold?

Vacation rentals in Southold have a price range between $83-$3,057. The average price for rentals in Southold is $487 per night.

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