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

Amagansett Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Amagansett vacation rentals

Terrace/patio

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (334 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is ￥21,043
￥28,384 total
includes taxes & fees
Nov 16 - Nov 17
Windward Shores Ocean Resort
A spacious hallway with high ceilings, arched columns, and chandeliers.

2. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,425 reviews)
"We’ve been to Montauk Manor many times. The inside pool area is updated and nice to use. Gavin a restaurant there is quite convenient. The units are comfortable and lovely with fully stocked kitchens."
United States
barbara
The price is ￥22,136
￥28,416 total
includes taxes & fees
Nov 30 - Dec 1
Montauk Manor
Front of property

3. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (461 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
The price is ￥21,733
￥26,566 total
includes taxes & fees
Nov 16 - Nov 17
Montauk Oceanside Suites
A patio with a wooden table and chairs, a door with a number, and a mailbox.

4. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is ￥35,935
￥79,192 total
includes taxes & fees
Nov 16 - Nov 17
Charming Accommodations in the Hamptons
A wooden deck with a white round table and two white cushioned chairs.

5. 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 ￥41,158
￥56,147 total
includes taxes & fees
Nov 16 - Nov 17
Offshore Spa & Residences
A house with a sliding glass door, a white door, and a small porch with potted plants.

6. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is ￥46,345
￥97,109 total
includes taxes & fees
Nov 16 - Nov 17
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A small cabin with a porch, surrounded by trees and a fenced area.

7. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is ￥35,935
￥79,375 total
includes taxes & fees
Nov 16 - Nov 17
Lovely studio with AC in charming Sag Harbor
A backyard patio with outdoor furniture, a large umbrella, and a stone fireplace.

8. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
United States
Suzanne B.
The price is ￥142,014
￥330,854 total
includes taxes & fees
Nov 22 - Nov 23
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
A rectangular swimming pool with a brick border, surrounded by lush green trees and a brick patio with white lounge chairs.

9. Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great clean beautiful property."
United States
ANGELA S.
The price is ￥112,116
￥212,395 total
includes taxes & fees
Dec 1 - Dec 2
Spacious house in East Hampton with heated pool + WFH
Terrace/patio

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ￥30,679
￥52,770 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

11. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is ￥13,655
￥36,402 total
includes taxes & fees
Nov 22 - Nov 23
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

12. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is ￥15,172
￥37,041 total
includes taxes & fees
Nov 30 - Dec 1
The SandPiper
A beach with sand dunes and a wooden bench.

13. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is ￥60,690
￥108,023 total
includes taxes & fees
Nov 17 - Nov 18
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

14. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
The price is ￥15,172
￥38,320 total
includes taxes & fees
Nov 18 - Nov 19
Aqua Vista
A modern wooden building with large windows, a balcony, and a view of autumn trees.

15. Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street

Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street
East Hampton
The price is ￥126,791
￥185,916 total
includes taxes & fees
Nov 16 - Nov 17
Serene Chic Hamptons oasis jus 1 block to waterfront + 8 minutes to Main Street
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

16. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ￥49,775
￥56,868 total
includes taxes & fees
Nov 16 - Nov 17
North Fork Resort
A beach with people relaxing, a pier extending into the water, and a clear sky.

17. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥20,842
￥55,561 total
includes taxes & fees
Nov 16 - Nov 17
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

18. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
The price is ￥9,575
￥72,542 total
includes taxes & fees
Nov 22 - Nov 23
Steps to the beach | Seabreeze Cottage #3
An outdoor dining area with hanging lights, palm trees, and a bar.

19. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is ￥31,782
￥45,983 total
includes taxes & fees
Nov 16 - Nov 17
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

20. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥31,143
￥68,424 total
includes taxes & fees
Nov 16 - Nov 17
Beach Block Hideaway
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"The stay was amazing. Great room, great amenities, great location, great staff!"
Juwon 1-night trip
Posted 2 hours ago
Offshore Montauk

Find out more about Amagansett

Search for holiday rentals in Amagansett on Expedia! You can easily find your home rentals, villas, holiday apartments in Amagansett using one of the methods below:

  • View our selection of featured holiday rentals in Amagansett
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  • Enter your travel dates to view the best deals on holiday rentals in Amagansett while they last

Look no further and take a look at our great range of rental properties in Amagansett!

Frequently asked questions

Can I find vacation rentals in Amagansett?

Yes, we offer vacation rentals near well known sights in Amagansett, or you can select a more remote 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 coffeehouses during your trip.

What are some of the best vacation rentals in Amagansett?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : You might want to consider this vacation home rental near Amagansett, which is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 vacation rentals are there in Amagansett?

With 123 Expedia vacation rentals, you're sure 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 vacation rentals like in Amagansett?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Amagansett. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for small groups.