Search Holiday Rentals in Amagansett

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Amagansett holiday rentals

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is £153
includes taxes & fees
17 May - 18 May
Windward Shores Ocean Resort

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (281 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is £184
includes taxes & fees
10 Jun - 11 Jun
The Surf Club

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is £153
includes taxes & fees
18 May - 19 May
Montauk Oceanside Suites

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is £691
includes taxes & fees
18 May - 19 May
Offshore Residences

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,343 reviews)
"Had a wonderful stay"
United States
Meghan
The price is £153
includes taxes & fees
27 May - 28 May
Montauk Manor

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is £236
includes taxes & fees
15 Jun - 16 Jun
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is £202
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is £157
includes taxes & fees
17 May - 18 May
Driftwood Resort

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is £456
includes taxes & fees
28 May - 29 May
Seabreeze 4 Charming Cottage walk to US Open

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is £237
includes taxes & fees
17 May - 18 May
American Beech in Greenport - Petite King Room 7

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
9.8 out of 10, Exceptional, (84 reviews)
"We had a wonderful stay at this cottage. It was 2 of us and 2 dogs. The property was perfect for the pups, had beautiful views of the water and walking distance to town. Very relaxing and had everything we needed for our stay. Pat was a great host and we will be back in the future!"
United States
LAURA
Cottage on Beach front Estate with Dockage .Walk to Village

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is £539
includes taxes & fees
17 May - 18 May
Northfork Townhouse walk to all

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
10.0 out of 10, Exceptional, (18 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is £641
includes taxes & fees
1 Jun - 2 Jun
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is £943
includes taxes & fees
20 May - 21 May
BlackBerry Private home with jacuzzi yearlong

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is £243
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
Renovated Townhouse walk to all

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is £1,250
includes taxes & fees
21 May - 22 May
Minutes from the beach, brand new 4 bedroom

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is £849
includes taxes & fees
18 May - 19 May
Beachfront Greenport Villa

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is £1,845
includes taxes & fees
18 May - 19 May
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Safari Tent Glamping,S6-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
United States
Lorraine
The price is £241
includes taxes & fees
31 May - 1 Jun
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
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.
Save an average of 15% on thousands of hotels when you're signed in

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 £153 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?

An awe-inspiring 8,000 SF custom oceanfront mansion retreat on two...: This highly rated holiday home rental in 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. It has 7 bedrooms, as well as a kitchen with a stovetop, a microwave and kitchenware, so that you can cook with friends or family. You can relax into your holiday with a balcony and 1 hot tub.

How many holiday rentals are there in Amagansett?

With 132 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.