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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
Stay at this vacation home in Southampton. Enjoy free WiFi, a garden, and patios. Popular attractions The Hamptons Beaches and Our Lady of Poland Catholic Church ...
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Stunning New Designer Renovation

Stunning New Designer Renovation

Sag Harbor
Book a stay at this business-friendly vacation home in Sag Harbor. Enjoy free WiFi, private pools, and a fitness center. Popular attractions The Hamptons Beaches ...
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
Stay at this vacation home in Montauk. Enjoy a fitness center, a garden, and an in-room coffeemaker. Popular attractions Second House Museum and Kirk Park Beach ...
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
Book a stay at this beach vacation home in Montauk. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Second House Museum and Kirk Park ...
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
Stay at this vacation home in Montauk. Enjoy free WiFi, a garden, and patios. Popular attractions Montauk Point and Amsterdam Beach State Park are located ...
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
Stay at this vacation home in Southampton. Enjoy free WiFi, private pools, and patios. Popular attractions The Hamptons Beaches and North Main Street Historic ...
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
Book a stay at this family-friendly vacation home in East Hampton. Enjoy private pools, a water park, and a fitness center. Popular attractions The Hamptons ...
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
Book a stay at this family-friendly vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and ...
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
Book a stay at this beach vacation home in Montauk. Enjoy a beach locale, a garden, and patios. Popular attractions Montauk Point and Second House Museum are ...
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
NZ$332
Highest Price
NZ$1,088
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 NZ$332 per night from 15 May to 16 May
NZ$332
includes taxes & fees
15 May - 16 May
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Windward Shores Ocean Resort
The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 out of 5
273 Main Street, Amagansett, NY
Stay at this 4.5-star luxury hotel in Amagansett. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Amagansett Square and Amelia Cottage ...
The Roundtree, Amagansett
Ocean Vista Resort

Ocean Vista Resort

2.5 out of 5
2136 Montauk Hwy, Amagansett, NY
Book a stay at this beach hotel in Amagansett. Enjoy free WiFi, free parking, and a private beach. Popular attractions Walking Dunes Trailhead and Hither Hills ...
Ocean Vista Resort
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The Hermitage

The Hermitage

3.5 out of 5
2148 Montauk Highway, Amagansett, NY
The price is NZ$1,088 per night from 31 May to 1 Jun
NZ$1,088
includes taxes & fees
31 May - 1 June
Stay at this 3.5-star beach hotel in Amagansett. Enjoy free WiFi, an outdoor pool, and a private beach. Popular attractions Walking Dunes Trailhead and Hither ...
The Hermitage
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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.