Beach HouseMontauk Surf House
Montauk · Long Island
4 bd3 baSleeps 10
Ocean viewBeach accessHeated pool
from $890 / night
New York
Long Island vacation rentals
Beach towns, wine country, and Hamptons-style escapes just outside NYC.
Best time to visit
Memorial Day through Labor Day for beaches; fall for wine harvest and quieter inns.
Rental types
Beach cottages · Hamptons estates · Vineyard guest houses · Soundfront homes
Getting there
Reach the Hamptons and North Fork by car via I-495/LIE; JFK and LaGuardia are the closest major airports.
Why Long Island rewards a rental stay
A rental gives you the full summer-house experience — morning coffee on a deck, beach gear in the garage, and room for friends. The Hamptons get the headlines, but North Fork and the South Shore offer more space for the money.
Many rentals are weekly in peak season, with Saturday-to-Saturday turnover. Off-season and midweek stays can be much more flexible.
Things to do
- Catch waves and sunsets at Montauk Point and Ditch Plains
- Taste North Fork wines in Mattituck, Cutchogue, and Greenport
- Ferry out to Fire Island's car-free beach communities
- Explore the mansions and gardens of the Gold Coast
- Dine on fresh seafood in Sag Harbor and Greenport
- Bike the boardwalks and nature trails of Jones Beach
Booking tips for Long Island
Hamptons prices spike in July and August. If your dates are flexible, June and September offer warm water and lower rates. North Fork is quieter and more affordable, while Fire Island rentals often require ferry logistics.
- Saturday-to-Saturday rentals are common in summer
- Confirm beach access and parking permits
- Fire Island homes may require carrying luggage from the ferry dock
- Book Montauk and Hamptons homes months ahead for peak season
Where to stay in Long Island
The Hamptons
East Hampton, Southampton, and Montauk — high-end beach living and surf culture.
North Fork
Wine country, farm stands, and relaxed waterfront villages like Greenport.
South Shore
Long Beach, Fire Island, and family-friendly Atlantic beaches.
North Shore
Gold Coast mansions, harbors, and easy access from New York City.
Example rentals in Long Island
Browse all Long Island rentalsBeach HouseGuest CottageNorth Fork Vineyard Cottage
Greenport · Long Island
2 bd1 baSleeps 4
Vineyard viewsPatioFireplace
from $325 / night
Estate Guest HouseHamptons Modern Pool House
East Hampton · Long Island
3 bd3 baSleeps 6
Private poolTennis court accessGated
from $750 / night
Long Island FAQs
How far is Long Island from NYC?
The North Fork is about 90 minutes by car; Montauk can be 3+ hours in summer traffic. The LIRR train serves many towns.
Can I visit Fire Island for a day?
Yes, via ferry from Bay Shore, Sayville, or Patchogue. Cars are not allowed in most Fire Island communities.
Is the Hamptons only for luxury travelers?
Not entirely. While estates dominate the high end, you can find more modest cottages and guest houses, especially outside peak weeks.
What's the North Fork like?
Laid-back wine country with farm stands, vineyards, and small villages. It's less scene-driven than the Hamptons and great for food and wine trips.
Keep planning
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