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Featured Holiday Homes in Amagansett

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
Located in Montauk, this vacation home is by the sea, within a 5-minute drive of The Hamptons Beaches and Second House Museum.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk
With a stay at this vacation home in Montauk, you'll be on the beach, just a 1-minute walk from The Hamptons Beaches and 10 minutes by foot from Second House ...
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Exquisite New Hampton Home in a Perfect Location

Exquisite New Hampton Home in a Perfect Location

East Hampton
Located in East Hampton, this vacation home is by the ocean, a 1-minute drive from Three Mile Harbor and 6 minutes from East Hampton Village Nature Trail and ...
Exquisite New Hampton Home in a Perfect Location
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COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

Amagansett
With a stay at this vacation home in Amagansett (Beach Hampton), you'll be steps from The Hamptons Beaches and 14 minutes by foot from Amagansett Beach.
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton
With a stay at this vacation home in Southampton, you'll be within a 5-minute drive of Southampton Golf Range and North Main Street Historic District.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Center of Town - Ideal for Beach, Golf & Tennis

Center of Town - Ideal for Beach, Golf & Tennis

Montauk
With a stay at this vacation home in Montauk, you'll be next to a golf course, just a 2-minute walk from Montauk Downs State Park Golf Course and 7 minutes by ...
Center of Town - Ideal for Beach, Golf & Tennis
Cozy Seaside Cottage

Cozy Seaside Cottage

New Suffolk
Located in New Suffolk, this vacation home is within a 5-minute drive of Pugliese Vineyards and Castello di Borghese / Hargrave Vineyard.
Cozy Seaside Cottage
East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms

East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms

East Hampton
Located in East Hampton (East Hampton North), this vacation home is within a 5-minute drive of Old Hook Mill and First United Methodist Church.
East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms
Beautiful Private 4 BR, Heated Pool. Close to Everything.

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

East Hampton
When you stay at this vacation home in East Hampton, you'll be near the beach, within a 5-minute drive of Three Mile Harbor and Pollock-Krasner House and Study ...
Beautiful Private 4 BR, Heated Pool. Close to Everything.
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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
1122 Holiday Homes
Lowest Price
AU$265
Highest Price
AU$1,141
Popular accommodation
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready, Unobstructed Ocean Views ! A Beautiful Montauk Getaway , Exquisite New Hampton Home in a Perfect Location, COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Center of Town - Ideal for Beach, Golf & Tennis, Cozy Seaside Cottage, East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms, Beautiful Private 4 BR, Heated Pool. Close to Everything.

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$265 per night from 5 Jan to 6 Jan
AU$265
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Windward Shores Ocean Resort in Amagansett, you'll be on the beach, just a 1-minute walk from Napeague State Park and 11 minutes by foot from ...
Windward Shores Ocean Resort
Sea Crest Resort

Sea Crest Resort

2.5 out of 5
2166 Montauk Hwy, Amagansett, NY
The price is AU$428 per night from 26 Dec to 27 Dec
AU$428
includes taxes & fees
26 Dec - 27 Dec
Located in Amagansett, Sea Crest Resort is on the beach, within a 5-minute walk of The Hamptons Beaches and Hither Hills State Park.
Sea Crest Resort
The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 out of 5
273 Main Street, Amagansett, NY
The price is AU$1,141 per night from 5 Jan to 6 Jan
AU$1,141
includes taxes & fees
5 Jan - 6 Jan 2025
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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Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State ...
Gurney's Montauk Resort & Seawater Spa
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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.