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Featured Holiday Homes in Amagansett

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Southampton
When you stay at this vacation home in Southampton, you'll be by the sea, a 4-minute drive from The Hamptons Beaches and 6 minutes from Cooper's Beach.
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Stunning New Designer Renovation

Stunning New Designer Renovation

Sag Harbor
With a stay at this vacation home in Sag Harbor, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Oakland Cemetery.
Stunning New Designer Renovation
4-bedroom house is across the street from private beach and walk to town

4-bedroom house is across the street from private beach and walk to town

2 out of 5
Montauk
With a stay at this vacation home in Montauk, you'll be within a 15-minute drive of The Hamptons Beaches and Montauk Point.
4-bedroom house is across the street from private beach and walk to town
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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
When you stay at this vacation home in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard

Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard

Montauk
When you stay at this vacation home in Montauk, you'll be on the beach, a 1-minute drive from The Hamptons Beaches and 6 minutes from Montauk Point.
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
Charming Village home in the heart of Southampton

Charming Village home in the heart of Southampton

Southampton
When you stay at this vacation home in Southampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.
Charming Village home in the heart of Southampton
Stunning Hampton Holiday Family Fantasy for your Team

Stunning Hampton Holiday Family Fantasy for your Team

East Hampton
With a stay at this vacation home in East Hampton, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and The Jewish Center of the ...
Stunning Hampton Holiday Family Fantasy for your Team
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton
Located in Southampton, this vacation home is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk
When you stay at this vacation home in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
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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
1431 Holiday Homes
Lowest Price
AU$307
Highest Price
AU$932
Popular accommodation
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 , Stunning New Designer Renovation, 4-bedroom house is across the street from private beach and walk to town , Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready, Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard, Charming Village home in the heart of Southampton, Stunning Hampton Holiday Family Fantasy for your Team , Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Top trending hotels in Amagansett

Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
The price is AU$307 per night from 6 May to 7 May
AU$307
includes taxes & fees
6 May - 7 May
When you stay at Windward Shores Ocean Resort in Amagansett, you'll be on the beach, within a 15-minute walk of The Hamptons Beaches and Napeague State ...
Windward Shores Ocean Resort
The Hermitage

The Hermitage

3.5 out of 5
2148 Montauk Highway, Amagansett, NY
The price is AU$932 per night from 4 Jun to 5 Jun
AU$932
includes taxes & fees
4 June - 5 June
When you stay at The Hermitage in Amagansett, you'll be by the ocean, within a 5-minute walk of The Hamptons Beaches and Hither Hills State Park.
The Hermitage
Ocean Vista Resort

Ocean Vista Resort

2.5 out of 5
2136 Montauk Hwy, Amagansett, NY
The price is AU$336 per night from 16 May to 17 May
AU$336
includes taxes & fees
16 May - 17 May
When you stay at Ocean Vista Resort in Amagansett, you'll be on the beach, and a 4-minute walk from The Hamptons Beaches and 8 minutes by foot from Napeague ...
Ocean Vista Resort
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The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 out of 5
273 Main Street, Amagansett, NY
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.
The Roundtree, 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.