The ultimate renter's guide to the Hamptons

Even though it’s only 90 miles from New York City, the Hamptons is another world filled with sandy beaches, quaint main streets, celebrities, and restaurants.

The Hamptons can make for a relaxing getaway, or a party-filled weekend. But no matter what you’re going for. one challenge remains: it can be extremely stressful to find a place to stay.

Since it’s officially Hamptons renting season, we broke down the 10 most popular hamlets by reputation, with suggestions for hotels, restaurants, and average rental prices from Memorial Day through Labour Day.

Keep reading to see our ultimate Hamptons rental guide for 2015.

East Hampton

When it comes to nightlife, East Hampton has you covered with raging dance clubs like SL East and the Pink Elephant.

It also has stellar beaches, tons of shopping, and top-notch restaurants. The ultra rich love East Hampton, especially away from the hustle and bustle of the public beaches, where glamorous homes can be found.

If you’re looking for a rental deal, look inland — the closer you are to the beach, the more expensive it will be. Plus, this is one of the most popular hamlets during the tourist season so it’s best to get your rental early.

Average Rental Prices for Memorial Day through Labour Day*: ~$US36,000 to ~$US150,000

Hotels: Baker House 1650, c/o The Maidstone, The 1770 House

Restaurants: Fresno, Nick & Toni’s, The Living Room, East Hampton Grill, Luigi’s Italian Specialties

Southampton

Southampton hamptonsAPSouthampton is for old money and billionaires.

Another popular town, Southampton puts all other villages to shame when it comes to three things: shopping, celebrities, and real estate.

This hamlet is packed with stores and is a favourite spot for people who have money and want to be seen. There are a lot of epic, multi-million dollar mansions that line the ocean as well as popular hotspots and restaurants where the blue bloods hang out.

Average Rental Prices for Memorial Day through Labour Day*: ~$US40,000 to ~$US210,000

Hotels: A Butler’s Manor

Restaurants: Saaz Indian Cuisine, Red Bar Brasserie, La Parmigiana Italian Restaurant

Sag Harbour

Aerial view sag harbour hamptonsJulie Zeveloff/Business InsiderSag Harbour is an artists’ enclave.

Known as a haven for artists, this former whaling village is one of the prettiest towns on the South Fork, with cute storefronts and old-school Hamptons appeal.

It also has fantastic real estate and a funky Main Street with delicious restaurants. Plus, it’s not too far from the popular Long Beach.

Average Rental Prices for Memorial Day through Labour Day*: ~$US27,000 to ~$US110,000

Hotels: The American Hotel

Restaurants: Estia’s Little Kitchen, The Dock House, The Beacon

North Haven

North Haven backyard sceneSotheby’s International RealtyThere’s not a whole lot to do in North Haven.

If Sag Harbour is where the wealthy artists live, than North Haven is its family-oriented suburb. The mansions here keep getting more and more expensive, but there’s not a whole lot to do in this tiny hamlet.

Renters can expect extremely high rental prices across the board, with plenty of deluxe mansions up for grabs. North Haven is located between East and Southampton and has a large amount of waterfront real estate, which also factors into the high price points.

Average Rental Prices for Memorial Day through Labour Day*: ~$US47,000 to ~$US190,000

Hotels: N/A

Restaurants: N/A

Westhampton/Westhampton Beach

Westhampton is the closest town on the list to New York City, meaning you’ll have a shorter commute as well as access to clean, beautiful beaches right off the exit.

This is a popular hamlet for people renting and co-renting homes. It has restaurants and stores to keep you busy, but is much more affordable than Southampton.

Average Rental Prices for Memorial Day through Labour Day*: ~$US40,000 to ~$US100,000

Hotels: Beaver Damn Creek House

Restaurants: Starr Boggs, Boom Burger, Pizzetteria Brunetti, The Patio Restaurant

Sagaponack

One of the oldest hamlets in the area, this tiny village is renowned for its rural beauty and has some of the most scenic beaches in the area.

The major downside of Sagaponack is that its too small for any theatres or shopping. For those, you would need to travel to nearby Southampton or East Hampton. But the real estate here is top notch — and über expensive.

Average Rental Prices for Memorial Day through Labour Day*: ~$US65,000 to ~$US290,000

Hotels: N/A

Restaurants: Sagg Main Store

Amagansett

Technically within the town of East Hampton, Amagansett has its own special style with delicious restaurants and really nice, sandy beaches.

Amagansett is a lovely resort town for the more low-key Hamptons visitor. It has great boutiques and a musical venue called Stephen Talkhouse where Jon Bon Jovi has performed unannounced.

Average Rental Prices for Memorial Day through Labour Day*: ~$US46,000 to ~$US170,000

Hotels: Hermitage Resort, Inn at Windmill Lane

Restaurants: Mary’s Marvellous

Water Mill

Wind mill at Water Mill new york hamptonsShutterstockWater Mill is super picturesque.

Artists, authors, and actors love Water Mill for its charming residential community. You’re not going to find a lot of parties or nightlife in this quiet hamlet, but if relaxation is what you’re after, Water Mill delivers.

But don’t let the pastoral setting fool you. Lots of celebrities and executives have homes here for the summer to capitalise on the idyllic surroundings.

Average Rental Prices for Memorial Day through Labour Day*: ~$US45,000 to ~$US150,000

Hotels: N/A

Restaurants: Robert’s, Sabrosa Mexican Grill

Montauk

Montauk surfing hamptons ditch plains beachFlicker/offmetro.comSurfers love Montauk.

During the day, surfers flock to Montauk’s Ditch Plains Beach for the best waves on Long Island before the pubs take over with a nightlife scene that draws both hipster and local crowds to this fisherman’s village.

Best for families, Montauk has become the most expensive place to stay in New York State. For tourist attractions, there are plenty of lighthouses to visit, beaches to walk down, and lobster to enjoy.

Average Rental Prices for Memorial Day through Labour Day*: ~$US50,000 to ~$US150,000

Hotels: Ruschmeyer’s, Panoramic View, Solé East Resort

Restaurants: St Peter’s Catch, Zum Schneider Montauk, South Edison, Dave’s Grill

Bridgehampton

Bridgehampton polo hamptonsTana Lee Alves/ShutterstockBridgehampton is big with the equestrian crowd.

Bridgehampton is a trendy vacation destination for the super rich — in fact, about two-thirds of its population are part-time home owners (which means rentals are not hard to come by!).

This town is really big with the equestrian crowd since Bridgehampton hosts the annual Hampton Classic Horse Show in late August. There are also cute boutiques, wineries, and restaurants for vacationers to try.

Average Rental Prices for Memorial Day through Labour Day*: ~$US60,000 to ~$US190,000

Hotels: Bridgehampton Inn

Restaurants: Mercado, Topping Rose House

*Note: 2015 rental price ranges were for current four-bedroom rental homes and were averaged from Memorial Day through Labour Day prices on Brown Harris Stevens, Sotheby’s International Realty, and Corcoran Real Estate. Ranges do not account for rental outliers.

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