Airbnb, Vacation Rentals in Southold, NY

Compare 5,426 available beachfront holiday vacation rentals, starts from $19

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ACCOMMODATION TYPES

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Airbnb, Vacation rentals and hotel deals in Southold, NY

American Beech in Greenport NY - King Suite 1
American Beech in Greenport NY - King Suite 1
Hotel · 1 Bedroom
$289 /night*
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Sea Haven Resort Motel
3.0 (131 reviews)
Sea Haven Resort Motel
Hotel · 1 Bedroom
$143 /night
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Lovely second story, two bedroom unit off main St
5.0 (3 reviews)
Lovely second story, two bedroom unit off main St
Apartment · 4 Guests · 2 Bedrooms
$301 /night*
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Peaceful and Private Shelter Island Getaway
4.9 (27 reviews)
Peaceful and Private Shelter Island Getaway
Holiday home · 6 Guests · 3 Bedrooms
$299 /night*
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Mattituck cottage ~ walk to private Bay Beach
4.9 (15 reviews)
Mattituck cottage ~ walk to private Bay Beach
Holiday home · 6 Guests · 3 Bedrooms
$300 /night*
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Evolve 2nd-Floor Apt half Mi to Greenport Harbor!
4.0 (1 review)
Evolve 2nd-Floor Apt half Mi to Greenport Harbor!
Apartment · 2 Guests · 1 Bedroom
$291 /night
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North fork Private exclusive Residence for Rent
North fork Private exclusive Residence for Rent
Holiday home · 12 Guests · 6 Bedrooms
$225 /night*
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American Beech Hotel
4.4 (397 reviews)
American Beech Hotel
Hotel · 1 Bedroom
$347 /night
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Bridgehampton Inn
4.6 (303 reviews)
Bridgehampton Inn
Hotel · 1 Bedroom
$285 /night
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The Cliffside Resort Condominiums
4.3 (135 reviews)
The Cliffside Resort Condominiums
Apartment · 4 Guests · 2 Bedrooms
$249 /night
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The Atlantic Hotel
3.5 (859 reviews)
The Atlantic Hotel
Hotel · 1 Bedroom
$186 /night
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Cozy Cottage on the North Fork Close to Vineyards & Beaches
5.0 (3 reviews)
Cozy Cottage on the North Fork Close to Vineyards & Beaches
Cottage · 2 Guests · 1 Bedroom
$275 /night*
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Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
5.0 (24 reviews)
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Cottage · 4 Guests · 2 Bedrooms
$300 /night*
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Sag Harbor Inn
4.5 (349 reviews)
Sag Harbor Inn
Hotel · 1 Bedroom
$294 /night
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Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!
4.9 (21 reviews)
Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!
Holiday home · 6 Guests · 3 Bedrooms
$315 /night*
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Harpoon House
4.0 (12 reviews)
Harpoon House
B & B · 2 Guests · 1 Bedroom
$248 /night
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Full waterviews, steps to the beach, kayaks available
4.5 (6 reviews)
Full waterviews, steps to the beach, kayaks available
Holiday home · 10 Guests · 5 Bedrooms
$254 /night*
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A Walk in the Woods Bed and Breakfast
4.6 (39 reviews)
A Walk in the Woods Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$320 /night
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Quaint Cottage Close to LI Sound
4.9 (75 reviews)
Quaint Cottage Close to LI Sound
Holiday home · 4 Guests · 2 Bedrooms
$265 /night*
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House on Chase Creek
4.0 (24 reviews)
House on Chase Creek
B & B · 2 Guests · 1 Bedroom
$210 /night
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Vacation Destinations Near Southold, NY

Airbnb, Holiday Beachfront House with Air Conditioning in Southold, NY

Open Floor Plan, Spacious and Private Backyard with Patio and Heated Pool,...
Air Conditioning
Open Floor Plan, Spacious and Private Backyard with Patio and Heated Pool,...
Holiday home · 8 Guests · 4 Bedrooms
$506 /night*
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Southampton Poolside Paradise
Air Conditioning
5.0 (4 reviews)
Southampton Poolside Paradise
Holiday home · 10 Guests · 5 Bedrooms
$975 /night*
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Luxury Waterfront, great WIFI, Dock, Kayak, Peloton, Paddleboards, HotTub, Pool
Air Conditioning
4.9 (50 reviews)
Luxury Waterfront, great WIFI, Dock, Kayak, Peloton, Paddleboards, HotTub, Pool
Holiday home · 14 Guests · 7 Bedrooms
$950 /night*
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What Are The Well Liked Rental Amenities in Southold, NY?
Trending Vacation Rental Amenities in Southold, NY
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There are in total of 15 rental amenities in Southold, shown above with the property numbers. In Southold, 2584 rentals offer Internet or Wifi, 2504 rentals offer Air Conditioning, 2400 rentals offer Parking Available. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pets Friendly.

What is the Best Time to Rent a Cheap Vacation Rental in Southold, NY?

Tips to Rent Vacation Rentals (Stay for a Week) for Cheapest Price in Southold, NY

Low Season
January
Most affordable month to stay
$159
Average rate of the cheapest vacation rentals option in low season month
High Season
July
Peak month to stay
$442
Average rate of the cheapest stay option in high season month
$442
Jul
$309
Aug
$300
Sep
$243
Oct
$162
Nov
$162
Dec
$159
Jan
$159
Feb
$159
Mar
$159
Apr
$159
May
$159
Jun
$375
Sun
$408
Mon
$425
Tue
$442
Wed
$458
Thu
$458
Fri
$442
Sat
Cheapest day of week
Sunday
Vacation rentals price normally the lowest on this day
$375
is the cheapest nightly rate for vacation rentals on this day
Highest day of week
Thursday
Most expansive day to book a vacation rentals
$458
is the highest nightly rate for vacation rentals on this day
Which Price Range Is Considered As A Good Deal in Southold, NY Area?
Vacation Rentals Price Information in Southold, NY
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The graph shows the percentages of vacation homes in each price bucket. Southold has the largest percentage (51.78%) of homes in $500+ price range.
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$300 to 350
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$450 to 500
$450 to 500
$500 +
$500 +
Which Accommodations Should I Pick in Southold, NY?
Best Accommodation Types in Southold, NY
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Before visiting Southold, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Cottage, Apartment, Estate, Farmhouse, Condo, Chateau / Country House, Townhome, Villa, Resort, Studio, Barn, Bungalow, Bed And Breakfast, Guest House, Hotel, Yacht, Cabin, Mobile Home, Chalet, Lodge. House is the most-liked rental type, with the largest percentage of 83.45%. The biggest home in this area available for rent is around 20000 square feet.The least popular accommodation in Southold is Chalet rentals
How Many Accommodations Are Pets Allowed in Southold, NY?
Percentage of Pet Friendly Vacation Rentals in Southold, NY
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35.02% of vacation homes in Southold are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Trail Recommendations in Southold, NY Area?
Best Trails In Southold, NY
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If you like outdoor activities, we highly recommend you to visit those famous trails: Long Pond Greenbelt Trail, Mountain Laurel Loop Trail, Morton National Wildlife Trail, Mashomack Preserve, Southold Bayview Trail, Hashamomuck Pond, Sound View Dunes Park Forest Trail, Horton Point Lighthouse, Arshamomaque Preserve Trails, Dam Pond Trail.
Where Are The Campgrounds in Southold, NY Area?
Top Rated Campgrounds In Southold, NY
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The best RV campgrounds here in Southold are: Niantic / I-95 Exit 72 KOA, Salem Farms Campground, Sunfox Campground, Grandview Camping Resort, Wolf's Den Family Campground, Odetah Camping Resort, Acorn Acres Campground, Nelson's Family Campground, Little City Campground, Markham Meadows Campground.
What are the Airports in Southold, NY?
Suggested Airports in Southold, NY
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Other Vacation Rentals Ideas

Airbnb, Holiday Beachfront House with Fireplace in Southold, NY

Historical Bed and breakfast<br>
Fireplace
2.0 (3 reviews)
Historical Bed and breakfast<br>
B & B · 12 Guests · 6 Bedrooms
$3,750 /night*
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3 BR East Hampton NW Cottage, Steps to Sammy's Beach
Fireplace
5.0 (5 reviews)
3 BR East Hampton NW Cottage, Steps to Sammy's Beach
Holiday home · 8 Guests · 4 Bedrooms
$472 /night*
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Close to Shinnecock: gracious home, salt water pool, billiards, piano, fireplac
Fireplace
Close to Shinnecock: gracious home, salt water pool, billiards, piano, fireplac
Holiday home · 10 Guests · 5 Bedrooms
$1,429 /night*
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Airbnb, Vacation Rentals, Cottage with Full Kitchen, and Other Rental Options in Southold, NY

Rustic Lodge - Ideal For the Fall foliage weekends,Holiday retreats
Full Kitchen
4.8 (15 reviews)
Rustic Lodge - Ideal For the Fall foliage weekends,Holiday retreats
Lodge · 6 Guests · 3 Bedrooms
$500 /night*
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Historic Sag Harbor Village Gem
Full Kitchen
4.9 (42 reviews)
Historic Sag Harbor Village Gem
Cottage · 2 Guests · 1 Bedroom
$500 /night*
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Pace's Place Close to North Fork Vineyards
Full Kitchen
4.8 (33 reviews)
Pace's Place Close to North Fork Vineyards
Cottage · 4 Guests · 2 Bedrooms
$375 /night*
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Airbnb, Pet Friendly Vacation Rentals, Cottage in Southold, NY

1- 2 bedroom apt on 9 acre estate property
Pets Welcome
4.6 (13 reviews)
1- 2 bedroom apt on 9 acre estate property
Cottage · 2 Guests · 1 Bedroom
$175 /night*
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Cottage on Beach front Estate
Pets Welcome
5.0 (18 reviews)
Cottage on Beach front Estate
Cottage · 6 Guests · 3 Bedrooms
$300 /night*
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Whaling Captain Pierson's Cottage
Pets Welcome
4.8 (40 reviews)
Whaling Captain Pierson's Cottage
Cottage · 2 Guests · 1 Bedroom
$315 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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