The 14 Dreamiest Island Airbnbs for Weekend Trips From NYC

Summer in New York City can be a lot — rooftop drinks at golden hour, yes; subway platforms that feel like kiln rooms and the smell of garbage in 90-degree heat, no thanks. By the time June rolls around, even the most committed New Yorkers start eyeing the calendar for a weekend getaway. And some of the easiest ways to escape the city are on islands just across the water.

There’s a whole lineup of beaches and islands within a few hours of the city. You’ve probably been to a few already, but this is the season to go back with a plan — not just for a beach day, but for a proper stay. A few days surrounded by water is often enough to clear your head and make the city feel a little less everything when you return.

On Block Island, you can hike through grassland trails that end in Atlantic views and spend the afternoon at peaceful beaches without cell service. Shelter Island has stretches of uncrowded shoreline and Airbnbs that feel like home by the second night. Fire Island brings energy in the summer, but step a few boardwalks away from the Pines or Cherry Grove, and you’ll find stretches of dune-backed sand where it’s surprisingly quiet. And then there’s Newport, where you can build a weekend around music festivals or birdwatching along the coast.

Once you’ve settled on an island, the place you stay can shape the entire trip. An Airbnb gives you more flexibility — space to spread out, a kitchen to cook in, and a better sense of what the place is actually like outside of the high season. I’ve rounded up Airbnbs across eight islands within an easy drive from the city, from breezy beach cottages and architectural stunners to private compounds with docks and views you can enjoy from a kayak. There are picks for groups, solo travelers, couples, families, and last-minute planners. I’ve also included seasonal events worth planning around, local spots to eat, and enough practical detail that all you really need to do is get a ferry ticket, a friend with a car, or the willingness to brave Friday traffic.

We hope you love the island Airbnbs near New York City we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.

Photo: Nicola Pulham / Shutterstock

The island is officially called Aquidneck, but for most people it’s just Newport. What makes it ideal for a weekend away isn’t just its shoreline or Gilded Age mansions, but how much there is to do without needing to drive far.

This year, the Newport Folk Festival (July 25 — 27) and Newport Jazz Festival (August 1 — 3) return to Fort Adams with lineups that pull bigger and more unexpected names every year — The Roots, De La Soul, and Janelle Monáe are all set to play. There’s also the Newport Classical summer season, which pairs chamber concerts with unexpected venues like vineyards, churches, and historic estates — and in May, the Newport Food Truck & Craft Beer Festival kicks off summer with local brewers and street food favorites.

Big-name festivals aside, this is an island best enjoyed outdoors. The Norman Bird Sanctuary has seven miles of trails through coastal woods and salt marshes, and is a favorite spot for local twitchers hoping to spot ospreys, egrets, and migrating shorebirds. Over at Brenton Point, the windy overlook is a go-to for picnicking, kite-flying, and watching seabirds ride the updrafts along the cliffs.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

If you’re staying with friends or family, this three-bedroom home in Portsmouth offers a quieter perch at the northern end of Aquidneck Island, with front-row views of the Mt. Hope Bridge and Hog Island Lighthouse. The house sits right on the island’s West Shore, and a private staircase off the back lawn leads directly to the beach — perfect for swimming, beachcombing, or watching the sunset roll in across Narragansett Bay. Floor-to-ceiling windows, vaulted ceilings, and an open-plan layout keep the interiors bright and breezy, while a wrap of couches in the living room makes the space ideal for unwinding after a day outside. You’ll be close to both Newport and Bristol, but you might find it hard to leave.

Or base yourself in a romantic Airbnb just outside downtown Newport, and you’ll be within walking distance of great restaurants like the recently opened Mediterranean eatery Flora, with breathtaking harbor views and a seasonal, seafood-forward menu inside the Gardiner House hotel and local institutions like The Black Pearl, famous for its clam chowder and dockside dining on Bannister’s Wharf.

Six guests, three bedrooms
Price: $450 per night

Photo: SEALANDSKYPHOTO / Shutterstock

Block Island sits just 13 miles off the coast of Rhode Island. It’s small — barely 10 square miles — but packed with coastal trails, swimmable beaches, and no-frills spots to eat, drink, and stay. Cars are allowed, but bikes and mopeds tend to take over in the summer. From New York, the most scenic route is to Montauk, then a ferry across.

If you haven’t been in a few years, the food scene has had a quiet glow-up. Payne’s Donuts is still essential for a paper bag of sugary crullers in the morning, and Persephone’s Kitchen does locally-sourced brunch. For lunch, The Surf is casual and chic for fish tacos with a view. At night, The National draws a steady crowd with live music, fire pits, and a menu that runs from fresh seafood to stacked burgers — a proper end-of-day spot after a day out on the island.

Once you’ve eaten your way through town, head out to the trails. Clay Head Trail (known locally as “the Maze”) winds through golden grasslands and ends at one of the best views of the Atlantic in the state. A few miles south, you’ll find Rodman’s Hollow — a 40-acre nature preserve carved by glaciers, where unmarked paths lead to spectacular views over the island’s southern coast. Crescent Beach and Mansion Beach offer swimmable stretches of sand and smaller coves and rocky outcrops reward anyone willing to veer off the main paths.

If you’re heading over in July, the island’s Fourth of July parade is worth planning around — it’s small, a little chaotic, and proudly homemade, with everything from fire trucks and decorated bikes to costumed dogs. Live music and pop-up food stands keep things going well past sunset.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Many of Block Island’s Airbnbs fall into two styles: classic beach houses that haven’t changed much in decades, and contemporary builds designed to frame the landscape. This three-bedroom home leans toward the latter. The stunning property is perched on the second highest hill on the island and offers floor-to-ceiling windows and sweeping views across the Atlantic and Long Island Sound.

Designed by Rhode Island–based architect Jim Estes, the house opens onto an open-plan main floor where the kitchen, dining, and living areas all connect, with glass doors leading out to a deck and shaded pergola perfect for al fresco meals. The bedrooms are simple and spacious, with a private balcony off the primary suite and additional sleeping options downstairs for larger groups. There’s a fire pit for cooler nights, a rain shower for sandy afternoons, and plenty of open lawn for kids (or adults) to sprawl, play, or take in the views. It’s just a short bike ride or drive from the ferry, the beach, and Mohegan Bluffs.

For something closer to town, this three-bedroom stay ($439 per night) in the heart of New Harbor offers walkable access to restaurants, marinas, and the ferry. It’s the only house in the commercial district, but it’s backed by open space, so the deck still feels private, with sunset views over the water.

Eight guests, three bedrooms
Price: $700 per night

Photo: James Kirkikis / Shutterstock

Fire Island is one of those places that hardly needs an introduction — especially if you’ve lived in New York long enough to start checking the ferry timetable as soon as it hits 70 degrees. You probably already know about the no-car policy, the boardwalks that double as runways, and the Pines vs. Grove dynamic. What’s easy to forget, though, is how many ways there are to experience the island, and how much is still happening beyond the social calendar.

The island is made up of around 17 communities. Ocean Beach is the most developed, with shops, a few bars, and the closest thing to a main street. Cherry Grove has long been a cultural hub for queer nightlife and creative energy, while the Pines is more polished and home to some of the island’s most architecturally ambitious houses. Other areas like Kismet, Atlantique, and Saltaire skew more residential and family-oriented, with quieter beaches and boardwalks that feel like an extension of people’s front yards.

There are nearly 30 miles of beach to explore, plus kayaking, clamming, tidepooling, and the elevated boardwalk through the Sunken Forest — a rare coastal woodland where American holly and other hardwoods grow in a protected hollow between the dunes.

But if you are going to party, this summer’s calendar brings plenty of reasons to visit. Highlights include the Fire Island Invasion (July 4 — 6), a wild celebration that spills from Cherry Grove into the Pines; the BOFFO Performance Festival (July 12), with art and music installations across the island; and the Fire Island Dance Festival (July 18 — 20).

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Staying on Fire Island in peak season means planning ahead. Many rentals book out months in advance, especially in the Pines and Cherry Grove.

One of the most sought-after Airbnbs on the island, this mid-century architectural standout is at the edge of the Fire Island National Seashore, with uninterrupted views of the dunes, ocean, and bay. The main house is pyramid-shaped and framed by a wall of glass that gives the open living, dining, and kitchen area the feel of a light-drenched lookout post. A double-sided fireplace anchors the space, while multiple dining areas — indoors, on the upper deck, and by the pool — make it easy to settle in for a full weekend.

The 800-square-foot master suite includes a California king, a private office, and sliding doors that open out to the pool deck. Across the way, two guest cabana rooms share a detached bathroom, offering just enough separation for groups traveling together. Outside, there’s a heated saltwater pool, a hot tub, and a full outdoor kitchen. It’s rare to find this kind of privacy with views like these — so if you’re visiting this summer (or even next), book like yesterday.

For something smaller — but no less charming — this two-bedroom cottage ($675 per night) sits a few houses from the ocean a short walk from the ferry. The multi-level wraparound deck is outfitted with comfortable outdoor furniture, perfect for pre drinks or dinners. It’s quiet, unfussy, and ideal for couples or solo travelers.

Six guests, three bedrooms
Price: $1,125 per night

Photo: cwieders / Shutterstock

Long Beach Island (LBI) doesn’t try to compete with flashier shore towns — which is exactly why people keep going back. It’s flat and easygoing, with miles of bikeable streets, low-rise beach houses, and boardwalks that lead straight into the sand. There’s no central scene — just a stretch of towns that each do their own thing, from the historic fishing docks of Barnegat Light to the arcades and oyster bars of Beach Haven.

Most New Yorkers drive the two hours (give or take, depending on how generous the Belt Parkway is feeling) to LBI. There’s a bus from Port Authority to Toms River, but you’ll still need a cab or ride-share for the last stretch. Either way, once you cross the bridge at Route 72, you’re in beach mode.

Beach Haven gets the most attention, and not just for its beaches — there’s a vintage amusement park, an old-school arcade, a local brewery, and a few decent spots for oysters and cocktails within walking distance of each other. Barnegat Light, at the opposite end, feels more residential, with commercial fishing boats docked just off the main drag and the lighthouse that gives the town its name open for climbs on clear days. In between are neighborhoods like Surf City and Loveladies — more spread out, quieter, and mostly residential, though you’ll still find a few charming coffee shops, general stores, and clam shacks along the way.

If you’re not on a towel or a surf board, there’s still plenty to do. Rent a bike and cruise the back roads, go crabbing in the bay, or walk the maritime forest trail at the Edwin B. Forsythe National Wildlife Refuge. Some come just for the birding, as the refuge is one of the best places in the state to spot herons and osprey in the wild.

Dining is low-key but improving. Delaware Ave. Oyster House in Beach Haven does local seafood right without trying too hard, while Raimondo’s in Ship Bottom leans more traditional Italian — white tablecloths and all. The Arlington is a good call for beer and burgers, and Blue Water Café does reliable brunch. Just know that in high season, most places fill up by early evening, so if you’re not on a patio with a drink by then, you’re probably waiting for one.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

After dinner, you could technically drive back, but it makes a lot more sense to stay the night. There’s no shortage of vacation rentals, but in high season, the good ones book fast. Airbnbs here range from classic shingled cottages to newer builds with outdoor showers and rooftop decks. Most are walkable to the beach, and a lot of them come with bikes, beach chairs, and a handwritten list of where to get the best crumb cake.

One standout is this four-bedroom waterfront home in Ship Bottom. Each bedroom has its own bathroom and a view of the water. A rooftop deck, private dock, and direct beach access make it easy to spend the day outside, whether you’re bringing paddleboards or just a book and a beach blanket.

Another option for groups is this newly built four-bedroom house ($1,500 per night) in Surf City, just two blocks from the beach. It sleeps up to 12, with multiple living spaces, a rooftop deck, and a private pool out back. There’s an elevator for easy access across floors, plus extras like bikes, beach gear, and even an ice maker in the garage for cooler refills before you hit the sand.

12 guests, four bedrooms
Price: $478 per night

Photo: Cavan-Images/ Shutterstock

You won’t hear anyone say Martha’s Vineyard is a cheap getaway — but for all its reputation, the island still feels grounded. Beyond the well-heeled visitors and historic homes, there are dusty bookstores in West Tisbury, old fishing boats out of Menemsha, and fried clams served on paper trays at roadside takeout windows. Nearly forty percent of Martha’s Vineyard remains in its natural state, making it the perfect getaway for nature lovers.

From New York, most people drive up to Woods Hole and catch the ferry to Vineyard Haven or Oak Bluffs. If you want to skip the traffic altogether, Seastreak runs a seasonal ferry from Manhattan that gets you there in just over five hours — slower than flying, but arguably more enjoyable.

This summer, Martha’s Vineyard is marking the 50th anniversary of Jaws with walking tours of filming locations, outdoor screenings, and talks with members of the original crew. On August 15, the annual Oak Bluffs fireworks return to Ocean Park, preceded by a concert from the Vineyard Haven Band.

Food-wise, in Vineyard Haven, The Maker Pasta Shop Café is opening in May and will likely become a neighborhood staple for a bowl of ragù and a glass of wine. For drinks, Bad Martha’s Brewery in Edgartown is still a reliable stop, and if you’re after something a little more dressed up, The Attic in Vineyard Haven has a well-curated wine list — mostly bottles, with a lovely by-the-glass selection and small plates.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Airbnbs here are on the higher side, especially in summer, but grab some friends, split the cost, and Martha’s becomes more than just a playground for the East Coast elite.

If you’re looking to stay somewhere that feels like its own little corner of the island, this five-bedroom home in West Tisbury fits. Set on over five acres along Watcha Pond, the property includes direct water access and a barrier beach just a paddle away. The main house was completed in 2024, with nearly every room facing the pond or the Atlantic. Outside, there’s a heated pool and hot tub tucked into native gardens, and kayaks and paddleboards ready to go.

For something smaller, this three-bedroom Cape-style home ($599 per night) is just outside Oak Bluffs. It offers gorgeous pond views, a deck for outdoor meals, a private patio off the primary suite, and a loft sleeping space.

10 guests, five bedrooms
Price: $1,350 per night

Photo: Bokic Bojan/ Shutterstock

Much like Martha’s Vineyard’s, Nantucket’s reputation tends to precede it: expensive, exclusive, and deeply seasonal. And while there’s truth to that, it doesn’t mean the whole island runs on rosé and white jeans. You’ll spot the designer sandals and champagne coolers, but you’ll also see fishermen unloading gear on the docks, fifth-generation locals running breakfast spots, and there’s a long list of things to do that won’t cost more than a bike rental.

For New Yorkers, getting there is straightforward. You can fly directly into Nantucket Memorial Airport or take Seastreak’s seasonal ferry from Manhattan, with a brief stop in Oak Bluffs. The more common option is to drive to Hyannis and catch the ferry from there — especially if you’re bringing bikes or beach gear for the weekend.

Some of the best things to do on Nantucket don’t cost anything. Dionis and Steps are quieter — ideal if you simply want to sit, read, or swim without the scene. Surfside and Cisco tend to draw bigger crowds, with surfers in the lineup, volleyball nets in the sand, and coolers packed for the day. The Sconset Bluff Walk winds along the eastern edge of the island past sea cliffs and weathered summer houses, with open views of the Atlantic. You can walk it out and back in under an hour, stop for photos near Sankaty Head Lighthouse, or detour into Sconset for coffee or a sandwich before looping back.

If you’d like to time your visit around an event, this summer’s calendar kicks off early: the Nantucket Wine & Food Festival runs May 14 — 18, followed by the Book Festival (June 12 — 15) and the Film Festival (June 25 — 30). July brings the Comedy Festival (July 10 — 12), and on August 9, the Boston Pops concert returns to Jetties Beach with fireworks and a stage set against the Atlantic.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Like Martha’s Airbnbs on Nantucket aren’t cheap, but they are gorgeous. If you’re browsing, it’s worth checking Airbnb’s Design Category — the rates are usually higher, but the properties tend to be more thoughtfully styled and comfortable for groups.

This six-bedroom home sits just outside Nantucket’s Historic District and works well for groups who want easy access to town. The layout spans three floors, with bedrooms on each level, including three on the ground floor. There’s a chef’s kitchen, a bluestone patio with a grill and dining setup, and off-street parking for multiple cars, which is rare for this part of the island. Town is about a 10-minute walk, and there are bikes if you’d rather ride.

For solo travelers or couples, a two-bedroom cottage ($680 per night) offers a quieter stay in a residential neighborhood near Surfside. You can walk to grocery stores, restaurants, and the local bus stop, and the beach is a five-minute drive. Inside, there’s a king bed in the primary bedroom, a rain shower and soaking tub in the main bath, and a washer and dryer for longer stays. The patio includes a grill and fire pit, with enough room to unwind outside without leaving the house.

13 guests, six bedrooms
Price: $700 per night

Photo: Joao Paulo V Tinoco/ Shutterstock

Getting to Shelter Island isn’t difficult — unless you try to leave Manhattan on a Friday after 3 PM. Most people drive, then take one of the two short car ferries: from Greenport on the North Fork or from North Haven near Sag Harbor. You don’t need a reservation, just line up and roll on. If you time it right, the whole trip takes about three and a half hours. If you don’t, you’ll be sitting in Hamptons traffic with everyone else who had the same idea.

Once you’re across, Shelter Island feels like a real island escape. It’s not as sleepy as the North Fork, nor as snooty as the Hamptons. It’s small enough to bike across (if you don’t mind the hills), and the close-knit community means that if you show up twice in one summer, the person pouring your coffee will probably remember your order.

There are four main beaches, and which one you choose mostly depends on what kind of day you’d like to have. Wades Beach is the most family-friendly, with lifeguards, bathrooms, and calm water. Crescent Beach (aka Louis’ Beach) is livelier, especially late in the day when the Sunset Beach crowd filters down the shoreline with drinks in hand. Shell Beach is a narrow stretch better suited to birdwatching and quiet walks. And Menhaden Lane, on the east side of the island, is where you go if you would like to get through a few uninterrupted chapters.

If you’re planning to park at any beach between May 15 and September 15, you’ll need a permit — either online through ParkMobile or in person at the Town Clerk’s office. Daily passes are $25, weekly is $100, and yes, they do check.

After a day at the beach, there are a handful of places worth planning your night around. This summer, Sunset Beach Hotel’s mezzanine is expected to fill up fast on weekends — especially Sundays — with DJs, drinks, and a crowd that leans more Sag Harbor than sleepy beach town, though weekday lunch remains an easy walk-in. Over at The Pridwin, the Terrace remains one of the best places on the island for a proper cocktail and sunset view, whether or not you’re staying there. Flora, inside the Gardiner House, continues to draw a steady crowd for Mediterranean plates and harbor views, but the bar at The Chequit tends to be easier to land a table at. Léon 1909 is still the spot for standout French-Italian, cooked over an open fire. But keep in mind it’s normally packed by 6 PM on weekends.

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Photo: Airbnb

Shelter Island isn’t huge, but where you stay makes a difference. Some people want to be near Sunset Beach for the social scene, others might prefer something with water access and a bit more privacy.

Set on seven acres at the end of a long drive on the Menantic Peninsula, this four-bedroom estate feels more like a private compound than a vacation rental. Every room looks out over the water, and the open-plan layout — cathedral ceilings, skylights, and oak floors — gives the interior an airy, all-day-bright feel. There are two balconies, a large gas fireplace, and a full chef’s kitchen with marble counters and high-end appliances. Outside, you’ve got direct beach access, a long dock for boating or fishing, and a sunset-facing hot tub that overlooks the bay. It’s quiet, private, and just a five-minute drive to town.

Or there’s this three-bedroom home near Hay Beach has garden-facing picture windows, a home office and gym, and a newly added barrel sauna off the lawn. It’s an easy pick for smaller groups looking for something relaxed and design-forward, just a short walk from quiet shoreline.

Eight guests, four bedrooms
Price: $959 per night