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

Amagansett Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Amagansett holiday rentals

Iron/ironing board, free WiFi, individually decorated

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 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 S$705
includes taxes & fees
9 Aug - 10 Aug
Windward Shores Ocean Resort
Iron/ironing board, free WiFi

2. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (439 reviews)
"The location is amazing, and the customer service is excellent. Unfortunately, the mattress and the air conditioning were the worst I’ve ever experienced, which made my stay much less comfortable."
United States
Carlos
The price is S$537
includes taxes & fees
3 Sept - 4 Sept
Montauk Oceanside Suites
Lobby

3. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,381 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is S$704
includes taxes & fees
13 Aug - 14 Aug
Montauk Manor
Terrace/patio

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (280 reviews)
"Great place!"
United States
Christine
The price is S$607
includes taxes & fees
9 Aug - 10 Aug
Cliffside Resort Condominiums
Living area

5. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (290 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is S$700
includes taxes & fees
3 Sept - 4 Sept
The Surf Club
Free WiFi, individually decorated, individually furnished, bed sheets

6. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (245 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is S$936
includes taxes & fees
6 Sept - 7 Sept
Driftwood Resort
Flat-screen TV

7. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is S$927
includes taxes & fees
10 Aug - 11 Aug
North Fork Resort
Living area

8. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 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 S$1,490
includes taxes & fees
11 Aug - 12 Aug
Offshore Spa & Residences
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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"I like"
Eliana 1-night trip
Posted less than an hour ago
The Bentley Hotel Southampton

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.

How many holiday rentals are there in Amagansett?

With 127 Expedia holiday rentals, you're guaranteed to find just the right place for your Amagansett stay.

What can I see and do in Amagansett?

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