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Hamptons.com
March 20, 2015

The Who, What, When And Where Of Hamptons Rentals

Sponsored Guest Post by Gary R. DePersiaby Sponsored Guest Post by Gary R. DePersia
in Real Estate
Home Real Estate

Each year, by this time, hundreds of people have been pondering the above questions concerning rentals in the Hamptons. Should they rent? What should they rent? When should they look? And, where should they be looking? Veteran renters wrestle with this quandary every year with some direction gleaned from past seasons of experience while first timers are sometimes overwhelmed with choices and questions. But there are some easy guidelines to help with these decisions.

The Who: If you’re looking for more than a weekend in the Hamptons, then you are probably looking for a home to rent. Unlike most resort areas, the choices of hotels and large condo complex rentals are limited on the East End in comparison to the number of people looking to spend time out here. The rental of a Hamptons home affords the space, privacy, amenities and ambiance not usually found in the limited number of hotels or inns scattered throughout the Hamptons. After all, it’s really inconvenient to go skinny dipping in the pool of a bed and breakfast with your significant other while the rest of the guests look on. Looking to buy? Then taking a test drive in a house or an area for a month or a summer could be the beginning of making that bigger decision.

The What: The larger the house, the more bedrooms, the better the amenities, and the more you are likely to pay. If costs are at all a factor, then it is imperative to figure out what you actually need. If it’s just you, your wife and two children most of the time, then resist looking at houses to accommodate a much larger group just because you are planning a big party one weekend. Don’t play tennis? Then don’t look at houses with tennis courts which will reduce your options and are bound to be much more money. Want waterfront but don’t have a boat? Then why do you need a house with a dock? Figure out what you actually need before embarking on your search. If you’re only going to use the house in July and August, then there is no need to spend the extra money for June when you might be overwhelmed with graduations, weddings or other June related activities. Ever think of an off-season rental? There are many options from mid-September through mid-May that are available at a fraction of the price of the summer season rates.

The When: When to start looking at rentals becomes a fine art for many veteran renters and should be for the “newbies” as well. There are many people who know where they want to rent and when they want to be there. For them, securing just the right house is much more important than saving money later on when landlords are more negotiable as the pool of renters starts to dwindle. Some of these savvy renters will start at the end of the previous summer season or during the fall to secure exactly what they want, knowing they will pay a fuller price. However, if you are flexible in your location, house choices, and amenities, then you might want to wait until later when landlords start to entertain lower offers. In addition, new options will appear on the market for shorter time frames as landlords hope to capture a broader range of people looking for partial season rentals.

The Where: If all of your friends are in East Hampton and your kids go to camp there, don’t look in Southampton which will add an hour of commuting each day and longer drives to see friends at night. If the focus of your weekends is not the beach, then it shouldn’t matter if you’re south of the highway or not. Why pay south of the highway prices if you want to hang out at your pool and tennis court all day with only occasional dips in the ocean?

Note to Landlords: First of all de-clutter. People have their own clutter at home and don’t want to deal with yours. If you have a bedroom that you use as an occasional office or den, return it to a true bedroom, if that’s not too difficult, as you get a larger pool of renters looking for more bedrooms and thus more money than you do for a cute den or office. And people… get rid of those boxy, 1980’s TVs. A good size flat screen in a living room or family room plus one in the master with smaller flat screens in the rest of the bedrooms goes a long way to attracting renters. When was the last time you checked into a decent hotel without one? Exactly!

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Spring Awakening: Toast To The End Of Winter With These Seven Spring-Themed Cocktails

Spring Awakening: Toast To The End Of Winter With These Seven Spring-Themed Cocktails

  • On August 25th, The Center at West Park held a special one-night-only reading of All The President’s Men at Guild Hall in East Hampton.⁠
⁠
📸: By Jessica Delane⁠
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#guildhall #centeratwestpark #easthampton #roberdowneyjr #markruffalo #reading
  • An inside look on the Hampton Classic
#hamptonclasic #horseshow
  • Check out the Top Hamptons Events This Weekend!⁠
⁠
⁠
📍 The Montauk General X Lands’ End⁠
🗓 Thurs, Aug 28 – Sun, Aug 31 | 10am–3pm⁠
📌 Montauk General Store at The Brunch Playhouse, 14 Amagansett Square⁠
🎁 Free limited-edition tote with orders over $100 (while supplies last)⁠
⁠
🐎 50th Annual Hampton Classic Horse Show⁠
🗓 Thurs, Aug 28 – Sun, Aug 31 | 8am–5pm⁠
📌 240 Snake Hollow Rd, Bridgehampton⁠
⁠
🍇 Wölffer Estate Vineyard PPL All-Star 2025⁠
🗓 Sat, Aug 30⁠
📌 Wölffer Estate Vineyard, Sagaponack⁠
🎾 World-class padel at the Hamptons’ most iconic vineyard⁠
⁠
😂 Zarna Garg at WHBPAC⁠
🗓 Sun, Aug 31 | 8pm–9:30pm⁠
📌 76 Main St, Westhampton Beach⁠
⁠
🎶 Joe Delia & Friends at The Clubhouse Hamptons⁠
🗓 Sun, Aug 31 | 6pm⁠
📌 174 Daniels Hole Rd, East Hampton⁠
⁠
🎧 Silent Disco Dance Party in the Garden⁠
🗓 Sun, Aug 31 | 8pm⁠
📌 Guild Hall, East Hampton⁠
⁠
👗 Marfa & Friends Trunk Show⁠
🗓 Thurs, Aug 28 – Sat, Aug 30⁠
📌 Sag Harbor⁠
⁠
🎬 Jaws’ 50th Anniversary Screening at Sunset Theater⁠
🗓 Fri, Aug 29 – Mon, Sept 1⁠
📌 Water Mill⁠
⁠
👠 Hamptons Fashion Week⁠
🗓 Sat, Aug 30 | 2pm⁠
📌 Location TBA⁠
⁠
🎸 Dogpark at The Stephen Talkhouse⁠
🗓 Sat, Aug 30 | 8pm⁠
📌 Amagansett⁠
⁠
🍴 Stirring The Pot: Florence Fabricant & Pete Wells⁠
🗓 Sun, Aug 31 | 11am–1pm⁠
📌 Guild Hall, East Hampton⁠
⁠
🌊 ANOTR at Surf Lodge⁠
🗓 Sun, Aug 31 | 4pm⁠
📌 Montauk⁠
⁠
🎷 Garden Concert ft. Freddy DeBoe⁠
🗓 Sun, Aug 31 | 6pm⁠
📌 Canoe Place Inn, Hampton Bays⁠
⁠
🔗 Link in Bio⁠
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#hamptons #wolffer #padel #landsend #montauk #fashion
  • Earlier this month, Shelter Island’s Rams Head Inn hosted a riveting Gilded Age Finale screening featuring lead actress Cynthia Nixon, award-winning costume designer Kasia Walicka Maimone, and executive producer/director Michael Engler.⁠
⁠
📸:Rob Rich/SocietyAllure.com⁠
⁠
Check out the full gallery at Hamptons.com (Link in Bio)⁠
.⁠
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#ramsheadinn #gildedage #shelterisland #cynthianixon #shelterislandny
  • Culinary and lifestyle icon Ina Garten will host an intimate tea and garden tour at her famed East Hampton residence on Wednesday, August 27th from 4:00 – 6:00 p.m. A limited number of guests will be invited to share tea with Ina and walk with her through her celebrated gardens and grounds.⁠
⁠
Known for her signature warmth and effortless approach to cooking and entertaining, Ina has earned a devoted following across generations. With her calm presence, foolproof recipes, and signature phrases like “store-bought is fine,” she takes the pressure off hosting, making room for only joy at the table.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
.⁠
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#hamptons #inagarten #community #easthampton
  • The magic of The Soho Sessions returns to the Hamptons this summer, bringing a rare and intimate live performance to Stephen Talkhouse in Amagansett on Monday, August 25, 2025. This one-night-only event features Grammy Award-winning artist Maren Morris (with introduction by the actor Jason Biggs) and the genre-defying powerhouse Yola in a night of music with purpose and soul.⁠
⁠
It’s also a night for change. The event supports Music Will, the largest nonprofit music education program for schools in the U.S., which aims to reach 10 million students annually by 2030. It’s a cause that hits home for Morris: “I loved my choir and theatre classes in high school; they really shaped my theory and love for being creative in every medium,” she recalls. “It also teaches you how to be a team player and work together.”⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
.⁠
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#stephentalkhouse #talkhouse #amagansett #marenmorris #yola #concert #hamptons
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