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Featured Holiday Homes in Amagansett

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Hampton Bays NY
When you stay at this vacation home in Hampton Bays, you'll be on the waterfront, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new windowBayfront 5 bedrooms family home. Panoramic sea view from all rooms
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
Located in Southampton, this vacation home is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new windowDelightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
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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
The price is AU$1,182 per night from 1 June to 2 June
AU$1,182
1 June - 2 June
includes taxes & fees
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new windowCharming Two-Story Retreat in Southampton Village walk to town, beach and train.
Vacation Getaway - Nature Retreat with Modern Comforts

Vacation Getaway - Nature Retreat with Modern Comforts

East Hampton NY
With a stay at this vacation home in East Hampton, you'll be within a 10-minute drive of The Hamptons Beaches and LongHouse Reserve.
Opens in a new windowVacation Getaway - Nature Retreat with Modern Comforts
Driftwood Cottage by Rove Travel | Serene Cottage

Driftwood Cottage by Rove Travel | Serene Cottage

East Hampton NY
With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and First United Methodist ...
Opens in a new windowDriftwood Cottage by Rove Travel | Serene Cottage
Beautiful Private 4 BR, Heated Pool. Close to Everything!

Beautiful Private 4 BR, Heated Pool. Close to Everything!

East Hampton NY
With a stay at this vacation home in East Hampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Three Mile Harbor.
Opens in a new windowBeautiful Private 4 BR, Heated Pool. Close to Everything!
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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 windowBlue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom

Southampton NY
The price is AU$1,545 per night from 15 May to 16 May
AU$1,545
15 May - 16 May
includes taxes & fees
With a stay at this vacation home in Southampton, you'll be within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new windowMinutes from the beach, brand new 3 bedroom
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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
1259 Holiday Homes
Lowest Price
AU$268
Highest Price
AU$1,545
Popular accommodation
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, The SandPiper , Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Charming Two-Story Retreat in Southampton Village walk to town, beach and train., Vacation Getaway - Nature Retreat with Modern Comforts, Driftwood Cottage by Rove Travel | Serene Cottage, Beautiful Private 4 BR, Heated Pool. Close to Everything!, Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office, Minutes from the beach, brand new 3 bedroom

Top trending hotels in Amagansett

Sea Crest Resort

Sea Crest Resort

2.5 out of 5
2166 Montauk Hwy Amagansett NY
The price is AU$344 per night from 28 May to 29 May
AU$344
28 May - 29 May
includes taxes & fees
When you stay at Sea Crest Resort in Amagansett, you'll be on the beach, just steps from The Hamptons Beaches and 6 minutes by foot from Hither Hills State ...
Opens in a new windowSea Crest Resort
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
The price is AU$283 per night from 17 May to 18 May
AU$283
17 May - 18 May
includes taxes & fees
With a stay at Windward Shores Ocean Resort in Amagansett (Napeague), you'll be within a 5-minute drive of The Hamptons Beaches and Hither Hills 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$1,316 per night from 19 May to 20 May
AU$1,316
19 May - 20 May
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
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Ocean Vista Resort

Ocean Vista Resort

2.5 out of 5
2136 Montauk Hwy Amagansett NY
The price is AU$268 per night from 17 May to 18 May
AU$268
17 May - 18 May
includes taxes & fees
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
Don't see what you're looking for?
See all available properties in Amagansett
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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.