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Airbnb, Vacation rentals and hotel deals in Southold, NY

Cozy family cottage on Shelter Island
Holiday home · 2 Guests · 1 Bedroom
$425 /night*
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6.0 (1 review)
Beautiful Cottage in private Sag Harbor community nxt to beach & nature preserve
Cottage · 2 Guests · 1 Bedroom
$650 /night*
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10 (16 reviews)
POOL + Private Beach near Greenport!
Holiday home · 2 Guests · 1 Bedroom
$600 /night*
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10 (8 reviews)
Shelter Island Hidden Waterfront Gem
Holiday home · 2 Guests · 1 Bedroom
$500 /night*
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9.0 (28 reviews)
House on Chase Creek
B & B · 2 Guests · 1 Bedroom
$166 /night
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9.8 (8 reviews)
Cozy Beach Cottage with private shared beach
Cottage · 2 Guests · 1 Bedroom
$350 /night*
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10 (17 reviews)
Newly-Renovated Modern Home+HotTub! Southampton/Sag Oasis Steps to Beach/Tennis
Holiday home · 2 Guests · 1 Bedroom
$850 /night*
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9.8 (17 reviews)
Southampton Private getaway. Private heated salt pool & beach-family fun.
Holiday home · 2 Guests · 1 Bedroom
$800 /night*
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9.8 (35 reviews)
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
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10 (36 reviews)
Renovated Sag Harbor Village 4 Bedroom With Pool + New Bronco with Beach Pass!
Holiday home · 2 Guests · 1 Bedroom
$1,250 /night*
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10 (27 reviews)
Historic Luxury Seaside Getaway
Holiday home · 2 Guests · 1 Bedroom
$795 /night*
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9.8 (24 reviews)
Relaxed Village Farmhouse
Holiday home · 2 Guests · 1 Bedroom
$500 /night*
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10 (3 reviews)
Gorgeous Four Bedroom Home in Sag Harbor with Pool/water access
Holiday home · 2 Guests · 1 Bedroom
$700 /night*
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9.8 (59 reviews)
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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8.0 (184 reviews)
Sound View Greenport
Hotel · 2 Guests · 1 Bedroom
$201 /night
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8.7 (150 reviews)
The Harbor Front Inn
Hotel · 2 Guests · 1 Bedroom
$167 /night
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9.8 (55 reviews)
Cottage on Beach front Estate
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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Southampton Stunner: Modern & Bright, Pool, Beach & More!
Holiday home · 2 Guests · 1 Bedroom
$950 /night*
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9.7 (39 reviews)
The Menhaden Hotel
Hotel · 2 Guests · 1 Bedroom
$336 /night
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10 (145 reviews)
Private & Spacious Five Room Suite<br>Steps To Bay Beach and walk to Village.
Apartment · 2 Guests · 1 Bedroom
$450 /night*
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Airbnb, Holiday Beachfront House with Air Conditioning in Southold, NY

ZEY HOTEL
B & B · 2 Guests · 1 Bedroom
$400 /night
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Rosemorran Retreat
Holiday home · 2 Guests · 1 Bedroom
$997 /night
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9.3 (3 reviews)
Arbor View House Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$394 /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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$100 to 150
$150 to 200
$150 to 200
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$200 to 250
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$250 to 300
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$300 to 350
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$350 to 400
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$450 to 500
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$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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Airbnb, Holiday Beachfront House with Fireplace in Southold, NY

9.8 (26 reviews)
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
Holiday home · 2 Guests · 1 Bedroom
$967 /night*
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9.8 (18 reviews)
Storybook Beautiful 3-Bedroom Cape
Holiday home · 2 Guests · 1 Bedroom
$350 /night*
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9.3 (3 reviews)
Arbor View House Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$394 /night
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Airbnb, Vacation Rentals, Cottage with Full Kitchen, and Other Rental Options in Southold, NY

9.8 (69 reviews)
'The Gate House' on Beach front Estate Walk to Village
Cottage · 2 Guests · 1 Bedroom
$250 /night*
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9.8 (59 reviews)
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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9.8 (55 reviews)
Cottage on Beach front Estate
Cottage · 2 Guests · 1 Bedroom
$300 /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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