Book Holiday Homes in Amagansett

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Amagansett

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

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

Southampton
Stay at this vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and Shinnecock Hills Golf ...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court-  WATCH VIDEO!!!

Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!

East Hampton
Book a stay at this golf vacation home in East Hampton. Enjoy private pools, a garden, and tennis courts. Popular attractions LongHouse Reserve and The Jewish ...
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Montauk
Stay at this vacation home in Montauk. Enjoy a beach locale, a garden, and patios. Popular attractions Second House Museum and Kirk Park Beach are located ...
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Save an average of 15% on thousands of hotels when you're signed in
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Greenport
Stay at this vacation home in Greenport. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Greenport Farmers' Market and Railroad Museum ...
Northfork Townhouse- walk to all/ newly renovated
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
Stay at this vacation home in Amagansett. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Amagansett Beach and Atlantic Avenue Beach ...
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 out of 5
Bridgehampton
The price is NZ$658 per night from 1 Dec to 2 Dec
NZ$658
includes taxes & fees
1 Dec - 2 Dec
Stay at this vacation home in Bridgehampton. Enjoy free WiFi, a garden, and patios. Popular attractions Channing Daughters Winery and South Fork Natural History ...
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Sagaponack
Stay at this vacation home in Sagaponack. Enjoy free WiFi, private pools, and a garden. Popular attractions Wolffer Estates Vineyard and SagPond Vineyards are ...
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton
Book a stay at this golf vacation home in East Hampton. Enjoy private pools, a water park, and a garden. Popular attractions Pollock-Krasner House and Study ...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Welcome to the J Luxury Southampton Estate w/Pool

Welcome to the J Luxury Southampton Estate w/Pool

Southampton
Stay at this vacation home in Southampton. Enjoy a sauna, onsite spa services, and balconies. Popular attractions Shinnecock Hills Golf Course and Shinnecock ...
Welcome to the J Luxury Southampton Estate w/Pool
Don't see what you're looking for?
See all available properties in Amagansett
View all properties
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
1132 Holiday Homes
Lowest Price
NZ$283
Highest Price
NZ$1,212
Popular accommodation
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!, Unobstructed Ocean Views ! A Beautiful Montauk Getaway , Northfork Townhouse- walk to all/ newly renovated, COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach, Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor , Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms, PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH, Welcome to the J Luxury Southampton Estate w/Pool

Top trending hotels in Amagansett

Sea Crest Resort

Sea Crest Resort

2.5 out of 5
2166 Montauk Hwy, Amagansett, NY
The price is NZ$415 per night from 8 Dec to 9 Dec
NZ$415
includes taxes & fees
8 Dec - 9 Dec
Book a stay at this beach hotel in Amagansett. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Walking Dunes Trailhead and Hither ...
Sea Crest Resort
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
The price is NZ$283 per night from 1 Dec to 2 Dec
NZ$283
includes taxes & fees
1 Dec - 2 Dec
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
The price is NZ$1,212 per night from 5 Dec to 6 Dec
NZ$1,212
includes taxes & fees
5 Dec - 6 Dec
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
Save an average of 15% on thousands of hotels when you're signed in
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is NZ$609 per night from 5 Dec to 6 Dec
NZ$609
includes taxes & fees
5 Dec - 6 Dec
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the room service in our reviews. ...
Gurney's Montauk Resort & Seawater Spa
Don't see what you're looking for?
See all available properties in Amagansett
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.