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Featured Holiday Homes in Amagansett

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk NY
When you stay at this vacation home in Montauk, you'll be on the beach, just steps from The Hamptons Beaches and 10 minutes by foot from Second House ...
Opens in a new windowUnobstructed Ocean Views ! A Beautiful Montauk Getaway
The SandPiper

The SandPiper

Greenport, NY
With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport ...
Opens in a new windowThe SandPiper
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton NY
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Southampton Golf Range.
Opens in a new windowDelightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
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Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Southampton NY
With a stay at this vacation home in Southampton, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and Southampton Historical Museum.
Opens in a new windowBeachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access

Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access

East Hampton NY
With a stay at this vacation home in East Hampton (Clearwater Beach), you'll be within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.
Opens in a new windowSerene Hamptons Retreat with Pool, Bocce Court & Private Beach Access
Aqua Vista

Aqua Vista

Greenport, NY
With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport ...
Opens in a new windowAqua Vista
1820 Whaling Captain's Home - A walk to a coffee or cocktail!

1820 Whaling Captain's Home - A walk to a coffee or cocktail!

Greenport NY
A stay at this vacation home places you in the heart of Greenport, within a 10-minute walk of Greenport Harbor Brewing Company and Eastern Long Island ...
Opens in a new window1820 Whaling Captain's Home - A walk to a coffee or cocktail!
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Montauk NY
With a stay at this vacation home in Montauk, you'll be on the beach, within a 5-minute drive of The Hamptons Beaches and Second House Museum.
Opens in a new windowHither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Southampton NY
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Southampton Historical Museum.
Opens in a new windowCharming Two-Story Retreat in Southampton Village walk to town, beach and train.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Amagansett Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Amagansett vacation homes are the perfect way for you to wing it.

Holiday houses in Amagansett let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Amagansett in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Amagansett adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Amagansett with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Amagansett vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Amagansett Holiday Homes essential information

Accommodation
1340 Holiday Homes
Lowest Price
AU$269
Highest Price
AU$1,006
Popular accommodation
Unobstructed Ocean Views ! A Beautiful Montauk Getaway , The SandPiper , Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️, Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access, Aqua Vista , 1820 Whaling Captain's Home - A walk to a coffee or cocktail!, Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready, Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Top trending hotels in Amagansett

Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
The price is AU$269 per night from 22 Mar to 23 Mar
AU$269
22 Mar - 23 Mar
includes taxes & fees
With a stay at Windward Shores Ocean Resort in Amagansett (Napeague), you'll be within a 15-minute walk of The Hamptons Beaches and Napeague State Park.
Opens in a new windowWindward Shores Ocean Resort
The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 out of 5
273 Main Street Amagansett NY
The price is AU$1,006 per night from 22 Mar to 23 Mar
AU$1,006
22 Mar - 23 Mar
includes taxes & fees
With a stay at The Roundtree, Amagansett in Amagansett (Amagansett North), you'll be within a 5-minute drive of Amagansett Square and Indian Wells Beach.
Opens in a new windowThe Roundtree, Amagansett
Sea Crest Resort

Sea Crest Resort

2.5 out of 5
2166 Montauk Hwy Amagansett NY
The price is AU$349 per night from 22 Mar to 23 Mar
AU$349
22 Mar - 23 Mar
includes taxes & fees
When you stay at Sea Crest Resort in Amagansett, you'll be on the beach, within a 5-minute walk of The Hamptons Beaches and Hither Hills State Park.
Opens in a new windowSea Crest Resort
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Ocean Vista Resort

Ocean Vista Resort

2.5 out of 5
2136 Montauk Hwy Amagansett NY
When you stay at Ocean Vista Resort in Amagansett, you'll be on the beach, within a 10-minute walk of The Hamptons Beaches and Hither Hills State Park.
Opens in a new windowOcean Vista Resort
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.