A coastal sunset with a beach, ocean waves, and a road leading to a distant town.

Holiday Rentals in Amagansett

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Our top choices for Amagansett holiday rentals

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (325 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is €167
includes taxes & fees
18 Oct - 19 Oct
Windward Shores Ocean Resort

2. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is €149
includes taxes & fees
13 Oct - 14 Oct
Driftwood Resort

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,415 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is €172
includes taxes & fees
2 Nov - 3 Nov
Montauk Manor

4. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (456 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is €154
includes taxes & fees
19 Oct - 20 Oct
Montauk Oceanside Suites

5. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (303 reviews)
"Staff are nice"
United States
na
The price is €272
includes taxes & fees
26 Oct - 27 Oct
The Surf Club

6. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
United States
Frank
The price is €436
includes taxes & fees
1 Nov - 2 Nov
Offshore Spa & Residences

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is €271
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums

8. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is €272
includes taxes & fees
13 Oct - 14 Oct
North Fork Resort
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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Top Amagansett Hotel Reviews

Find out more about Amagansett

Everything you need to know about Amagansett holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Amagansett holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Amagansett holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Amagansett holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Amagansett. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Amagansett holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Amagansett holiday rentals we have selected for you start as low as €149 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Amagansett rentals

At Expedia, we put the best Amagansett holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Amagansett rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Amagansett holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Amagansett. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Amagansett?

Yes, there are holiday rentals close to the most popular sights in Amagansett, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Amagansett. Make sure you have time to check out the seafood restaurants and coffee shops during your trip.

What are some of the best holiday rentals that Amagansett has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Amagansett is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many holiday rentals are there in Amagansett?

With 123 Expedia holiday rentals, you're guaranteed to find just the right place for your Amagansett stay.

What can I see and do in Amagansett?

Indian Wells Beach and Amagansett Beach are a couple of scenic spots to enjoy the outdoors, whereas Amelia Cottage Museum is one of the cultural attractions. While here, Hither Hills State Park and The Hamptons Beaches are other places worth a visit.

What are holiday rentals like in Amagansett?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Amagansett. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.