Tips for Booking your Summer Hamptons Rental

By HRES Staff - July 2, 2019

So, you’re finally spending a summer in the Hamptons, or maybe you’re just seeking a new town out on the South Fork for a change in beach scenery. With so many options (seriously, which beach? What town do I want to be closest to? Am I going for young and carefree, or a kid-friendly environment?), you may be scratching your head wondering determining your perfect fit may seem a bit easier with a few of these tips…

Book Early.

If you’re reading this right now, you should be booking your rental for summer 2020 (yes, I know, we’re in 2019). Of course, you’ll still be able to snag a coveted pied-à-terre for short term, but your options will be limited and the price points will have less room to budge. 

Know the Rules.

The Hamptons take pride in what/who they are, and they do so by establishing guidelines that prevent overcrowding while ensuring the safety and peace of all. Each township has its own rules, but most hamlets require 14-night minimum stays, including East Hampton and Southampton. These rules have been established to maintain the Hamptons’ low-key yet luxe ambiance. Note: some hamlets simply have restrictions; others require actual permits for your stay.

Most Hamptons towns rely on homeowners and residents to stay on board with the reasoning behind the regulations, so they’re not strictly enforced by the town, but if you’re a homeowner renting the property out, failure to abide by the rules will open you up to liability and/or risk if there is another violation or circumstance that draws attention to the rental, such as excessive noise or accidents (like an accidental smoke alarm from a cooking incident…little things you have to keep in mind!). As a renter, in most agreements, if you break any rules – regardless of how minor – the owner has the right to evict your rental with no refund regardless of how many nights you have left.

Finding Your Perfect Hampton Fit

Your perfect fit is a determined by your budget and what vibe you’re aiming for during your stay. What can you expect to pay? It’s not all about million-dollar rentals like this $1.4 million Southampton mansion (yes, that is about $467,000 per month); in fact, the average seasonal rental is somewhere around $60,000 (about $30,000 per month), but you can generally find smaller cottages for $15,000 per month – perfect for a romantic getaway.

The search: if you’re looking up rentals online, don’t be surprised if you see the same rental 2, 3, even 10 times – Hamptons rentals are not exclusive listings, meaning anyone can list them/

Ocean proximity: Rule of thumb: closer to the ocean (in Hamptons language, “south of the highway”) = more expensive.

Keep in mind, if you are getting a deal on a house that’s not as close to the ocean, it may not be the hop, skip, and jump across the street to the beach you have in mind; it often ends up as more of a 10-15 minute car ride, and if that’s the case, you could be looking at the need for special parking passes, which will run you approximately $375 for the season (regardless of how long you’re there) and tend to sell out long before the summer starts – good news is, you may be able to use this lack of day pass included in your rental as a reason to get a lower price. 

Beach parking day passes are available, but tend to sell out first thing in the morning – so wake up bright and early if you want one! Biking is always an option, as is a free shuttle that runs daily (but hey, it’s vacation – don’t you want to run on your own schedule?).

City proximity: are you running far, far away from the city and have no intention of looking back until the season’s over, or do you see yourself needing to make it back to the city relatively frequently through the duration of your stay?

  • If you’re escaping every aspect of the city: we suggest Montauk (the furthest away you can get), East Hampton, or Sag Harbor.
  • If you’re going to need to get back to the city and don’t want the stress of traffic to give you a heart attack before you get there: we suggest Quogue, Hampton Bays (both the closest to the city, and also generally more budget-friendly), or Southampton.
  • If you want to be central: Southampton is home to the most restaurants, shops, and activities – though all Hamptons have their own little village, if you have a family (or a large group of people) who are always needing distraction other than the beautiful beaches, consider staying in, or close to, Southampton.

Your time: just because rentals tend to be listed at “seasonal” (full summer) rates doesn’t mean you must rent the entire season; it may be better for your schedule – and your budget – to just rent 2-4 weeks, and that’s totally fine. 

No matter which hamlet you choose, we’re sure that a summer in the Hamptons will leave you coming back for more – there’s nothing like the salty ocean air and the warm, starlit nights that you’ll experience here.

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