Amagansett Vacation Rentals

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Our top choices for Amagansett vacation rentals

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is CA $218
CA $286 total
includes taxes & fees
May 12 - May 13
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,332 reviews)
"Incredible place to stay "
United States
melissa
The price is CA $207
CA $263 total
includes taxes & fees
May 25 - May 26
Montauk Manor

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $296
CA $339 total
includes taxes & fees
May 5 - May 6
North Fork Cottages & RV Resort

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
The price is CA $169
CA $208 total
includes taxes & fees
Apr 29 - Apr 30
Montauk Oceanside Suites

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is CA $229
CA $336 total
includes taxes & fees
May 11 - May 12
The Surf Club

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $229
CA $321 total
includes taxes & fees
May 11 - May 12
Cliffside Resort Condominiums

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is CA $294
CA $443 total
includes taxes & fees
May 25 - May 26
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is CA $294
CA $440 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

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 CA $231
CA $362 total
includes taxes & fees
Apr 28 - Apr 29
American Beech in Greenport - Petite King Room 7

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is CA $213
CA $288 total
includes taxes & fees
May 17 - May 18
Driftwood Resort

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is CA $750
CA $1,013 total
includes taxes & fees
Apr 29 - Apr 30
Offshore Residences

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is CA $294
CA $457 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

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 CA $492
CA $964 total
includes taxes & fees
Apr 28 - Apr 29
Northfork Townhouse walk to all

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 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 CA $923
CA $1,915 total
includes taxes & fees
Apr 29 - Apr 30
Minutes from the beach, brand new 4 bedroom

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $601
CA $1,142 total
includes taxes & fees
May 12 - May 13
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is CA $5,467
CA $8,779 total
includes taxes & fees
May 2 - May 3
Spacious 5-bedroom house with water views and 2 houses from the bay.

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 CA $1,729
CA $2,394 total
includes taxes & fees
Apr 28 - Apr 29
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is CA $3,690
CA $7,403 total
includes taxes & fees
Apr 28 - Apr 29
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is CA $1,229
CA $2,118 total
includes taxes & fees
May 1 - May 2
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Amagansett. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

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

How many vacation rentals are there in Amagansett?

With 131 Expedia vacation rentals, you're sure to find just the right place for your Amagansett stay.

What can I see and do in Amagansett?

The Hamptons Beaches and Amagansett Square 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 Indian Wells Beach 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.