Amagansett Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Amagansett

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (285)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is AU$509
includes taxes & fees
22 June - 23 June
Windward Shores Ocean Resort

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1198)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is AU$673
includes taxes & fees
22 June - 23 June
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (383)
"great place to stay"
The price is AU$347
includes taxes & fees
23 June - 24 June
Montauk Oceanside Suites

Offshore Montauk

4.0 star property
The price is AU$791
includes taxes & fees
26 June - 27 June
Offshore Montauk

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (223)
"The staff was very friendly I will definitely be back again 👍"
The price is AU$619
includes taxes & fees
22 June - 23 June
Driftwood Resort

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (256)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is AU$478
includes taxes & fees
1 July - 2 July
The Surf Club

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (221)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is AU$531
includes taxes & fees
22 June - 23 June
Cliffside Resort Condominiums

3-bedroom Montauk Coastal Getaway

3-bedroom Montauk Coastal Getaway

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (66)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Charming Montauk Getaway centrally located

9.6 out of 10, Exceptional, (43)
"Quiet, private, well-appointed spot with everything you need for a getaway. Conveniently located within walking distance to town, it has its own outdoor area perfect for lounging and cooking out. We loved it!"
Charming Montauk Getaway centrally located

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

10.0 out of 10, Exceptional, (5)
"Michael's cottage was incredibly well-appointed. The location to Southampton, Coopers Beach and neighboring townships made this very convenient for my trip. The true star of this cottage is the upstairs deck which was perfect for relaxing and stargazing. I will certainly return next summer. "
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (86)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

10.0 out of 10, Exceptional, (83)
"Great time"
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

9.4 out of 10, Exceptional, (10)
"I stayed here with family recently and loved the house. The location was private and convenient. The management company was available to answer our questions. It was perfect for an off season get away. "
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

10.0 out of 10, Exceptional, (7)
"We thoroughly enjoyed the home, and Carter was extremely helpful throughout our stay. The private parking access to the beach was awesome!"
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (7)
"Great place! Great communication with property owner!"
The price is AU$717
includes taxes & fees
23 June - 24 June
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

9.8 out of 10, Exceptional, (100)
"Had a great experience at this property!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (26)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
The price is AU$930
includes taxes & fees
23 June - 24 June
Location and views! Located directly on Shinnecock Bay!

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

9.8 out of 10, Exceptional, (87)
"This unit is just gorgeous breathtaking views!!!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
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

Frequently asked questions

Can I find holiday rentals in Amagansett?

Yes, there are holiday rentals in Amagansett close to Shinnecock Museum, 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?

3-bedroom Montauk Coastal Getaway: This holiday home rental outside of Amagansett offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Amagansett?

With 135 Expedia holiday rentals, you're guaranteed to find just the right place for your Amagansett stay.

What can I see and do in Amagansett?

Cultural attractions include Sag Harbor Whaling Museum and Amelia Cottage Museum, whereas Atlantic Avenue Beach and Amagansett Beach are a couple of picturesque spots to enjoy the outdoors. 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.