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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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LOCAL EVENTS

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Aperitivo (Sunset Cocktails)

October 9 @ 05:00 PM - October 9 @ 08:00 PM
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Emilio Moro Wine Dinner at R.AIRE

October 9 @ 06:30 PM - October 9 @ 08:30 PM
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R.AIRE Wine Dinner with Emilio Moro

October 9 @ 06:30 PM - October 9 @ 09:30 PM
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“The First Science from the Vera Rubin Observatory” (A Free, Virtual Lecture)

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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

  • The 33rd Hamptons International Film Festival kicked off last Friday with the U.S. premiere of A24’s Eternity starring Elizabeth Olsen, Miles Teller, and Callum Turner.⁠
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Elizabeth Olsen attended the premiere on Friday, and on Saturday sat down with IndieWire’s Editorial Director Kate Erbland at the Sag Harbor Cinema as a part of the festival’s “A Conversation With” series. Later that day, the second “A Conversation With” took place as Ethan Hawke and moderator Alison Stewart talked about Blue Moon, as well as Hawke’s filmography. ⁠
⁠
Sydney Sweeney received the festival’s Achievement in Acting Award following the U.S. premiere of her film Christy in East Hampton. ⁠
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Notable Guests included: Alessandro Nivola, Alec Baldwin, Amanda Peet, Tonatiuh, Miriam Shor, Lois Smith, Tim Blake Nelson, Mareille Enos, Bob Balaban, E. Jean Carroll, Roberta Kaplan, Ellen Barkin, Bernie Telsie, Bill Condon.⁠
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📸: Jess Dalene⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hiff #hamptonsinternationalfilmfestival #film #elizabetholsen #sydneysweeney #hamptons #hamptonsfilm⁠
  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
  • From world premieres at the Hamptons International Film Festival to SouthamptonFest! ⁠
⁠
Check out the Top Hamptons Events This Weekend!⁠
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🎬 33rd Hamptons International Film Festival⁠
📅 Oct 3 – 13, 2025 | 9AM – 10PM⁠
📍 Various Locations⁠
A global lineup of films, shorts & documentaries.⁠
⁠
🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
⁠
🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
⁠
🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
⁠
💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
📍 East Hampton⁠
Dance the night away w/ DJ Chile & more!⁠
⁠
🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
📍 Amagansett Life Saving Station⁠
Taste clam chowder, clam pies & cheer on the winners!⁠
⁠
🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
📍 Southampton Cultural Center⁠
Free community jazz jam – all are welcome.⁠
⁠
🌕 Full Hunter’s Super Moon Hike⁠
📅 Oct 6, 2025 | 6:30PM – 7:30PM⁠
📍 SOFO Museum Parking Lot⁠
Guided evening hike under the moonlight.⁠
⁠
✨ Which event are you most excited for?⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #hamptonsinternationalfilfestival #hiff #jazz #fullmoon #hike #film #levainbakery #community
  • So many fun fall activities in the Hamptons 🎃

@fairviewfarmatmecox 
@corwithsfarmstand 
@milkpailfarmorchard 

Check out our fall guide at Hamptons.com (Link in Bio)

#hamptons #fall #applepicking🍎 #pumpkin #maze #pettingfarm
  • As summer winds down and the cool breezes of fall approach, jewelry enthusiasts and fashion lovers alike are looking for the latest seasonal trends. Yael Fraynd, founder and president of Yaya Publicity, offers an insider’s perspective on what to expect this fall — especially for those embracing the chic lifestyle of the Hamptons.⁠
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Looking ahead to fall, Fraynd described the evolving styles with enthusiasm. For fall, expect to see bold statement pieces, rich gemstone colors like orange and a playful mix of metals. ⁠
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She also noted the influence of pop culture on jewelry trends, including celebrities like Taylor Swift, who is recently engaged, saying, “It could also be just, you know, with Taylor Swift, who has such a big effect on what people like.”⁠
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On the seamless transition from summer to fall styles, she observed, “In the summer, you see a bit of Western-inspired pieces, and I think that they really do kind of transition into fall really nicely. ⁠
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@yayapublicity⁠
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Read the full article at Hamptons.com (Link in Bio) ⁠
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#fall #falltrend #falljewelry #hamptons⁠
  • Apollo in the Hamptons returned with a celebratory evening at the EHP Resort & Marina (Si Si Restaurant) in East Hampton. The annual fundraiser supported Apollo’s year-round artistic and educational programs and its first full-scale renovation and restoration. ⁠
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📸: Danté Crichlow for The Apollo⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#apollo #apollotheater #hamptons #easthampton #benefit #fundraiser
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