Amagansett Holiday Rentals

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Holiday Rentals in Amagansett

View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$387
per night
29 May - 30 May
Windward Shores Ocean Resort
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1022)
"Best affordable hotel in Montauk"
The price is NZ$499
per night
12 Jun - 13 Jun
Montauk Manor
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very good, (220)
"Very nice location and nice condo"
The price is NZ$346
per night
29 May - 30 May
The Surf Club
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Apartment | Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (299)
"Great place to stay"
The price is NZ$314
per night
12 Jun - 13 Jun
Montauk Oceanside Suites
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (187)
"Well maintained upscale resort. "
The price is NZ$298
per night
30 May - 31 May
Driftwood Resort
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is NZ$506
per night
23 Jun - 24 Jun
Cliffside Resort Condominiums
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (62)
"Pictures don’t do it justice! So relaxing. Quiet and clean. Best we could ask for. The deck is great. It was bit cold so we couldn’t use the pool but we would love to be back for the summer! Very close to close to everything but still extremely quiet. Kelly was also an amazing host. She responded quickly and assisted with a parking question we had. Couldn’t ask for anything more. 5 stars!"
Newly Renovated Montauk Condo with Ocean Views!
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (72)
"We had the best time at Rick’s house in the Hamptons! We’d love to come back!"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (25)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Lobby
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (28)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (73)
"We enjoyed our stay. No complaints. Great location."
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
The price is NZ$972
per night
13 Jun - 14 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
On the beach, sun-loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (91)
"Had great time at property. Very close to town and beach. Would highly recommend."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Lobby
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
Beach
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
9.8 out of 10, Exceptional, (31)
"The cabin was cosy and functional, and in a quiet location. Very happy."
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
Microwave, oven, stovetop, coffee/tea maker
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
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See all available properties in Amagansett
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.

Other types of properties in Amagansett you may be interested in

Studio Unit Upper Oceanfront 'San Remo'  | Terrace/patio
Sea Crest Resort
2.5 star property
9.0 out of 10, Wonderful, (364)
"Amazing. I will come again "
The price is NZ$310
per night
29 May - 30 May
Sea Crest Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$387
per night
29 May - 30 May
Windward Shores Ocean Resort
Beach nearby, white sand, sun-loungers, beach umbrellas
The Roundtree, Amagansett
4.5 star property
9.8 out of 10, Exceptional, (75)
"The best hotel in the Hamptons! Luxury hospitality without pretension. Quiet, simple and the only one worth the price tag. You will pay the same if not more at any other local hotel and receive the worst service. It would be so easy for Roundtree to just rely on the high summer months to make money and rob you because they can, but they don't. The whole team works with an integrity uncommon to the area. Easy walk to everything in town and while they don't have a restaurant or bar they make up...
The price is NZ$1,104
per night
3 Jun - 4 Jun
The Roundtree, Amagansett
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Amagansett holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Amagansett. 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 Amagansett. 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 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 holiday 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 Amagansett short-term rentals, that won’t be hard to do.

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?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: This holiday home rental outside of Amagansett offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Amagansett?

With 145 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 Amelia Cottage Museum and East Hampton Historical Society, whereas Amagansett Square 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.

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