Vacation Rentals in Suffolk County NY
Explore Red Cottage’s collection of Suffolk County vacation rentals on Long Island, where the city finally loosens its grip and the coastline takes over. From the wide, golden beaches of the Hamptons to the vineyard-lined roads of the North Fork, Suffolk County is the kind of destination where every weekend feels like it was designed for exactly this: salt air, great food, and a house that makes you want to stay an extra night.
Whether you’re after a quiet surf town morning in Montauk, an afternoon tasting your way through North Fork wineries, or a long weekend in a design-forward home steps from the beach, Suffolk County delivers without trying too hard. If upstate is more your speed, our Catskills vacation rentals and Hudson Valley vacation rentals offer a different kind of escape, but when the plan is sun, salt, and seafood, Long Island is where you want to be. Our homes come equipped with full kitchens, outdoor entertaining spaces, pools, and the kind of thoughtful details that turn a rental into a real getaway. Browse below to find your next Long Island escape.
What Guests Are Saying About Their Suffolk County Stay
We stayed here for our wedding weekend and we never wanted to leave! The home and property are absolutely beautiful, exactly as pictured. We will definitely be back! This home will always hold a special place in our heart.
My family had a great 10 day stay! Felt right at home and really got to relax and enjoy the peaceful pool/hot tub! Highly recommended!
Beautiful property with everything we needed, loved the pool & hotub after visiting nearby beach!
An excellent property in a very convenient area. Can enjoy both the north and south fork options when it comes to things to do and amenities, the house in great shape, modernized amenities and a peaceful backyard. Would stay again no questions!
House was very welcoming and as described in the ad. Host communication was speedy and helpful. Would definitely stay again!
This divine spot was a haven of nature and delightful moments spent sitting in and around the gorgeously designed and furnished countryside modern & uber comfortable beach cottage…. We loved the bikes too!
Discover Suffolk County
Suffolk County spans the eastern stretch of Long Island, and it rewards the kind of trip where you let the day unfold. Beaches, wine trails, fishing villages, farm stands, and some of the best restaurants within driving distance of the city are all here, and none of it feels rushed.

Suffolk County’s coastline is the main event, and it earns it. On the South Shore, Coopers Beach in Southampton and Main Beach in East Hampton consistently rank among the best in the country, with wide sand, clean water, and a scene that manages to feel both polished and relaxed. Head farther east and Ditch Plains in Montauk is where the surfers go, while Ponquogue Beach in Hampton Bays is a local favorite for families and sunset watchers. Most of our Suffolk County homes put you within a short drive of all of it, so a full day on the sand still ends with a hot shower, a home-cooked meal, and your own deck at golden hour.

The North Fork is Long Island’s wine region, and it has quietly become one of the best tasting trails on the East Coast. Start at Macari Vineyards in Mattituck for a tasting with views that stretch across the fields to the Sound. Croteaux Vineyards in Southold is all rosé, all the time, and it works. Bedell Cellars and Sparkling Pointe are worth a stop, especially if you’re building the afternoon around a few pours and a long lunch. The whole corridor from Riverhead to Greenport is easy to cover in a day, with farm stands, roadside produce, and enough character to keep the drive interesting.

Some of the best days in Suffolk County happen between plans. Sag Harbor is a former whaling village with bookshops, galleries, a restored cinema, and the kind of Main Street that makes an afternoon feel like a proper outing. Greenport, on the North Fork, has a walkable waterfront, a classic carousel, and a food scene that punches well above its size. Montauk village is more laid back, with fish markets, surf shops, and a harbor that still feels like a working town. And Shelter Island, accessible only by ferry, is the kind of place where the pace drops the moment you drive off the boat.

For a proper outdoor reset, Suffolk County has more options than most people realize. Ditch Plains in Montauk is the go-to surf spot, with consistent breaks that draw everyone from beginners to regulars who have been coming for years. The Peconic Bay side is built for kayaking and paddleboarding, with protected waters and access points scattered from Riverhead to Southold. On Shelter Island, the Mashomack Preserve is 2,000 acres of trails, tidal creeks, and coastal forest, and it feels a world away from the South Fork scene. Montauk Point State Park offers cliffside hikes and views from the lighthouse that are worth the drive alone.
The food scene in Suffolk County is reason enough to book the trip. In East Hampton, Nick and Toni’s is a local institution with wood-fired Italian that has earned its reputation over decades. The Crow’s Nest in Montauk is a waterfront spot where the lobster roll and the sunset compete for your attention. For something more casual, the Clam Bar at Napeague is a roadside seafood stand that has become a rite of summer for anyone driving between Amagansett and Montauk. On the North Fork, Noah’s in Greenport and First and South in the same town are excellent picks for a meal that feels elevated without the scene.
Suffolk County Through the Seasons
Suffolk County takes on a different character with each season, every one offering its own unique charm. Use the guide below to compare typical weather, crowds, and rates so you can plan around beach days, wine tasting, fall foliage, or a quiet winter reset.
| Month | Typical Weather | Avg Temp (°F) | Crowd Level | Nightly Rates | Best For… |
|---|---|---|---|---|---|
| January | ❄️ Cold, quiet | 25–38 | Low | $ | 🏠 Off-season deals, cozy weekends, empty beaches |
| February | ❄️ Cold, crisp | 26–40 | Low | $ | 🏠 Winter escapes, romantic getaways |
| March | 🌨️ Chilly, thawing | 32–48 | Low | $ | 🚗 Early spring drives, shoulder-season pricing |
| April | 🌸 Cool, bright | 42–58 | Low – Medium | $$ | 🌿 Blooming gardens, opening weekends, farm stands |
| May | 🌿 Mild, fresh | 52–67 | Medium | $$ | ⛵ Beach walks, vineyard openings, Memorial Day |
| June | 🌤️ Warm, early summer | 62–77 | High | $$$ | 🏖️ Beach season starts, surfing, outdoor dining |
| July | ☀️ Hot, peak summer | 68–83 | Very High | $$$$ | 🎉 Full beach mode, festivals, farm-to-table dining |
| August | ☀️ Hot, humid | 67–82 | Very High | $$$$ | 🏄 Surfing, kayaking, long weekends, Montauk |
| September | 🌙 Warm days, cool nights | 60–75 | Medium – High | $$$ | 🍷 Wine harvest, fewer crowds, perfect beach weather |
| October | 🍁 Crisp, fall color | 49–63 | Medium | $$ | 🚗 Fall foliage, harvest festivals, scenic drives |
| November | 🌨️ Cool, quiet | 39–52 | Low | $ | 🏠 Peaceful stays, off-season charm |
| December | ❄️ Cold, festive | 30–42 | Low – Medium | $$ | 🎄 Holiday escapes, winter beach walks, cozy nights |
Frequently Asked Questions
Most of Suffolk County is about 1.5 to 2.5 hours from Manhattan by car, depending on where you’re headed and how traffic cooperates. The Hamptons and Montauk are roughly 2 to 3 hours via the Long Island Expressway or Sunrise Highway. The LIRR also runs to several Suffolk County towns, making a car-free trip possible if you plan ahead.
Coopers Beach in Southampton, Main Beach in East Hampton, and Ditch Plains in Montauk are the headliners. Ponquogue Beach in Hampton Bays is a favorite for families. On the North Shore, the quieter bay beaches offer a calmer, more private experience. If you’re looking for something different, take the ferry to Shelter Island for a truly secluded beach day.
Summer (June to August) is peak season for beach days and outdoor dining, with rates and crowds to match. September and October offer warm weather, thinner crowds, and wine harvest season on the North Fork, making them a great sweet spot. Winter and early spring are quiet and affordable, ideal for a low-key escape.
Pet policies vary by home. Check each listing for details on pet-friendly options, any associated fees, and house rules. Many of our properties welcome dogs, so your trip doesn’t have to start with a goodbye at the door.
Beyond the beaches and wine country, you’re also within reach of our Sullivan County vacation rentals for a mountain and river-town experience on the same trip. If you’re looking to extend your stay or plan a second getaway, the Catskills and Hudson Valley are only a few hours north.