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Hamptons.com
May 23, 2023

Can’t Miss Hamptons Rentals: Memorial Day–Labor Day

David Andrewsby David Andrews
in Real Estate, Trending
Home Real Estate
Can’t Miss Rentals: Memorial Day–Labor Day

Below are some of the hottest rental properties still available from Memorial Day thru Labor Day. This guide is organized by hamlet with a range of price points. Listings are provided by the Hamptons’ largest locally-owned brokerage Firm, Saunders & Associates. 

 

Additional rental dates are available; please contact the listing agent for more details!

 

West of the Canal


35 Beach Lane, Quogue

MD–LD: $315k

Aimee Fitzpatrick Martin || (631) 357-0016 || [email protected] 

 

 

33 Dolphin Road, East Quogue

MD–LD: $45k

Camille C. Cutler || (917) 756-5550 || [email protected] 

 

14 East Rampasture Road, Hampton Bays

MD–LD: $40k

The Laura Dalessandro Team || (419) 340-4154 || [email protected] 

 

 

Southampton – South


1880 Meadow Lane, Southampton

MD–LD: $650k

The Vince Horcasitas Team || (516) 768-7330 ||[email protected] 

 

 

1431 Meadow Lane, Southampton

MD–LD: $500k

Mark Greenwald || (917) 596-4426 || [email protected] 

 

272 Downs Path, Southampton

MD–LD: $120k

Drew Green || (516) 314-2508 || [email protected] 

 

23 Pulaski Avenue, Southampton Village

MD–LD: $90k

The Wines Team || (631) 876-5826 || [email protected] 

 

 

Southampton – North


184 Big Fresh Pond Road, Southampton

MD–LD: $135k

Susan Penzner || (917) 680-1909 || [email protected]

 

78 Sandy Hollow Road, Southampton

MD–LD: $175k

Krae Lylla Team || (516) 769-7877 || [email protected] 

 

 

Water Mill


5 Reed Pond Court, #5, Water Mill

MD–LD: $97k

Ed Gaetjens || (201) 707-7178 || [email protected] 

 

235 Roses Grove Road, Water Mill

MD–LD: $550k

Hans F. Von Schirach || (516) 901-2344 || [email protected] 

 

 

Sag Harbor Village


40 Lincoln Street, Sag Harbor

MD–LD: $275k

Peter Cook || (631) 806-2772 || [email protected] 

 

233 Madison Street, Sag Harbor

MD–LD: $180k

Susan Lahrman || (631) 506-1353 || [email protected] 

 

94 Brandywine Drive, Sag Harbor

MD–LD: $120k

The Connolly Team || (631) 259-6224 || [email protected] 

 

 

Sag Harbor Town


9 Margaret Drive, Sag Harbor

MD–LD: $85k

Sarah Doud || (631) 745-2127 || [email protected]

 

1635 Sagg Road, Sag Harbor

MD–LD: $50k

Susan Lahrman || (631) 506-1353 || [email protected] 

 

895 Brick Kiln Road, Sag Harbor

MD–LD: $65k

Drew Green || (516) 314-2508 || [email protected]  

 

 

Shelter Island


1887 Dering Harbor Village, Shelter Island

MD–LD: $120k

Penelope A. Moore || (917) 208-5519 || [email protected] 

 

 

Bridgehampton


252 Highland Terrace, Bridgehampton

MD–LD: $450k

Whitney St. John Fairchild || (631) 680-7097 || [email protected]

 

773 Ocean Road, Bridgehampton

MD–LD: $295k

Vincent Horcasitas || (516) 768-7330 || [email protected] 

 

 

Sagaponack


69 Soctline Drive, Sagaponack

MD–LD: $250k

Laura White || (631) 478-8385 || [email protected] 

 

749 Sagg Main Street, Sagaponack

MD–LD: $150k

Jane Gill || (516) 909-9591 || [email protected] 

 

Wainscott


107 Town Line Road, Wainscott

MD–LD: $250k

Nancy Mizrahi || (917) 854-9933 || [email protected] 

 

5 Judson Lane, Wainscott

MD–LD: $255k

Stephen J. Hartigan || (917) 843-8907 ||[email protected] 

 

 

East Hampton Village


8 Toilsome Lane, #8, East Hampton Village

MD–LD: $255k

The Wilson Team || (631) 219-2771 ||  [email protected] 

 

37 Church Street, East Hampton

MD–LD: $160k

John Pizzo || (631) 377-1434 || [email protected] 

 

25 Mcguirk Street, East Hampton

MD–LD: $140k

William Schumann || (631) 335-5151 || [email protected] 

 

 

Northwest Woods


12 Harbor Street, East Hampton

MD–LD: $90k

The Connolly Team || (631) 259-6224 || [email protected] 

 

3 Rolling Wood Lane, East Hampton

MD–LD: $90k

Rebecca Underdown || (760) 208-8880 || [email protected] 

 

 

Springs


563 Springs Fireplace Road, East Hampton

MD–LD: $75k

Alfredo Barreto || (631) 255-1854 || [email protected] 

 

21 Tyrone Drive, East Hampton

MD–LD: $39k

Darius Narizzano || (631) 255-0169 || [email protected] 

 

 

Amagansett


197 Skimhampton Road, Amagansett

MD–LD: $500k

Ed Bruehl || (646) 752-1233 || [email protected] 

 

80 Osprey Road, Amagansett

MD–LD: $65k

Sarah Minardi || (631) 987-8916 || [email protected] 

 

 

Montauk


90 Grant Drive, Montauk

MD–LD: $85k

Gary Cooper || (917) 969-0203 || [email protected]

 

75/81 East Lake Drive #6, Montauk

MD–LD: $25k

 John Capano || (917) 626-8086 || [email protected] 

 

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LOCAL EVENTS

Events

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Aperitivo (Sunset Cocktails)

October 9 @ 05:00 PM - October 9 @ 08:00 PM
The Baker House 1650
09
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09
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Emilio Moro Wine Dinner at R.AIRE

October 9 @ 06:30 PM - October 9 @ 08:30 PM
259 East Montauk Hwy, Hampton Bays, NY, 11946
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R.AIRE Wine Dinner with Emilio Moro

October 9 @ 06:30 PM - October 9 @ 09:30 PM
259 E Montauk Hwy, Hampton Bays, NY 11946
09
Oct
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“The First Science from the Vera Rubin Observatory” (A Free, Virtual Lecture)

October 9 @ 07:00 PM - October 9 @ 08:00 PM
Hamptons Observatory with Suffolk County Community College (online)
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Rita Cantina Reopens in East Hampton for the Season

Rita Cantina Reopens in East Hampton for the Season

  • 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.⁠
⁠
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. ⁠
⁠
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.⁠
⁠
📸: Jess Dalene⁠
⁠
⁠
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!⁠
⁠
🎬 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.⁠
⁠
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. ⁠
⁠
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.”⁠
⁠
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. ⁠
⁠
@yayapublicity⁠
⁠
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. ⁠
⁠
📸: Danté Crichlow for The Apollo⁠
⁠
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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