Sign up for our Newsletter

Homes like this one on Dignans Road in Cutchogue offer breathtaking seaside views. (Photo courtesy of Town & Country Real Estate)

Even though spring is not officially here, it’s not too late to think about summer. Summer rentals, that is. 

“if you’ve been sleeping this winter, this month is the time to wake up and get out. By April, it will be too late,” says Town & Country agent Nicholas Planamento, a veteran in the Hamptons market who handles both sales and rentals. 

“The 2024 market came in with a boom and really started at the end of summer 2023 when many people renewed their [existing] leases,” Planamento says. “Between fall and the new year, many of the best rentals are taken.” Compounding that is a rental market that now reflects substantial home improvements—a trend driven by people who stayed at home during the coronavirus pandemic.

“Homeowners who invested time and money in amenities and improvements know they can charge top of the range and are not willing to rent for less,” the agent said. Though pricing has eased a bit since the height of the pandemic, he says “once that barn door is open, you never really close it.” 

Despite the challenges, Planamento says there are plenty of opportunities for those who want to shake a leg—fast. Here are a few to consider. Now, get hopping!

2430 Dignans Road, Cutchogue

As they say, go big or go home. And if you choose the former, then this four-bedroom, 3.5-bath house on the cliffs is your end-of-summer rental, available only for August through Labor Day. What’s “big” about this house, smack on Duck Pond Point, is the view over Long Island Sound,. The house leverages its privileged location with a wrap-around deck, windows everywhere, cathedral ceilings with skylights, and a windowed sunroom. The downstairs open format includes plenty of spaces for gathering. The upstairs mezzanine is equipped as a work space with a reading nook and telescope for stargazing. Bedrooms are in a connected annex with deck and pool access, and its own elevated deck. The large deck with its pool and hot tub is the spot for swimming, sunning, supping and staring over the water. A private walkway leads to the beach.

Pricing: $40,000/month

1600 Westview Drive, Mattituck

Coastal meets a little bit of country in this three-bedroom, three-bath home with flexible renting options. On a peninsula in Mattituck Inlet and at the gateway to wine country, you can indulge your passions for both water and wine. The 3,192-square-foot house features a light-filled open format on the first level, high ceilings, large windows and a gas-powered fireplace. The fully equipped chef’s kitchen can handle gatherings large and small; in addition to the outdoor entertainment space, there is a separate dining room. Upstairs bedrooms include a primary king suite with a spa bathroom and water views. The lower level features a media room, and two other areas in the house offer separate work spaces. Outside, you can watch the world go by from the front porch, or be secluded in the back yard with a fire pit, fully equipped cooking station with BBQ and pizza oven and al fresco dining area. 

Pricing: May (not including Memorial Day weekend): $10,000; June: $15,000; July: $18,000; August through Labor Day weekend: $20,000. Other options include July 1 through Labor Day: $38,000, September (not including Labor Day weekend): $10,000. For partial months, a two-week minimum is required.

1695 Old Woods Path, Southold

This circa 1880 six-bedroom, four-bathroom house offers both tree-lined privacy on Hog Neck Bay, a sugar-sand beach and proximity to town and North Fork amenities and attractions. Rustic paneling and beams ceilings, a wood-burning fireplace and homey touches throughout give this home away from home a nostalgic theme that recalls summer memories at the beach. Plenty of porches for spending time with a book, a cup of tea or a glass of wine, a large dining room for family and friends, and an outbuilding with dormitory-style space and private bath for overflow guests. Pets considered. Tenant pays all utilities and insurance required. 

Pricing: Memorial to Labor Day: $75,000; July $25,000; July to August: $55,000; August to Labor Day: $30,000. Off season pricing available.

11120 Main Road, East Marion

Water, water all around this house on Gardiner’s Bay overlooking Bug Light and Long Beach. In addition to the bay, Marion Lake is nearby and the grounds include a heated, waterside pool. The four-bedroom, two-bath home offers one-level living with an expansive southeast-facing back deck and yard. Floor-to-ceiling windows and sliding doors offer the consummate indoor/outdoor living. Inside offers an eat-in-kitchen and dining room, a living room fireplace, sunroom that doubles as an office or game room. Close proximity to area farmstands, lavender fields, wineries and destination restaurants in Greenport.

Pricing: April and May: $7,000/month; June: $20,000. The home is rented July to Labor Day and available again for the balance of September into October (request pricing for fall and later off-season)

430 Terry Lane, Southold

If you believe less is more, then this cozy boho cottage is for you. Perfect for a solo season or with another, this one-bedroom sunny home sits near Town Creek and Southold Bay beach by Founder’s Landing Park. Though compact, it has all the conveniences, including a full kitchen with dishwasher, breakfast bar and dining area. The private park-like grounds are lush with greenery, flowering shrubs and grasses, and sunny seating areas looking out toward the water. Private and pet friendly.

Price: Memorial to Labor Day: $19,000; June: $4,500; July: $7,000; August to Labor Day: $8,000; $2,300/month in winter/other off season.