Vacation rentals in Amagansett

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Top-rated vacation rentals in Amagansett

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Guest favourite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Nov. 23 – 30

$840 CAD per night

Guest favourite

Cabin in Montauk

4.96 out of 5 average rating, 423 reviews

Montauk | Tiny Cottage in Private Hither Woods

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Sep. 11 – 18

$557 CAD per night

Guest favourite

Home in Amagansett

4.96 out of 5 average rating, 75 reviews

Casa Amagansett

*REMODELED FEB 2022* Casa Amagansett is a classic Hamptons bungalow, 3 minutes from the beach. Our 3br/2b home features a beautiful kitchen with 2 sinks, a laundry room, a truly sunny Sunroom, and gorgeous outdoor space. We are perfectly situated minutes from the beach, the Amagansett LIRR train station, grocery stores, and great shops & dining. There are four bicycles available for easy breezy access to everything nearby. Suitable for couples, families, business travelers, and friends.

Sep. 26 – Oct. 3

$800 CAD per night

Guest favourite

Home in East Hampton

4.95 out of 5 average rating, 371 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and check-out are NOT available in season

Jun. 6 – 13

$982 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 28 reviews

Storybook Cottage Seconds to East Hampton Village

Beach Cottage at edge of East Hampton Village. This fresh and bright cottage with three bedrooms and two new bathrooms is a compact and convenient jewel box with everything you'd expect in the Hamptons - including a beautiful pool with built-in hot tub. Just blocks from the heart of East Hampton on a quiet no-traffic cul-de-sac, not far from beach, shopping, dining and train... sparkling kitchen with new 'retro style' appliances, gleaming hardwood floors throughout, and a cozy front porch.

Oct. 23 – 30

$781 CAD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 119 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

May 21 – 28

$1,187 CAD per night

Guest favourite

Home in East Hampton

4.96 out of 5 average rating, 55 reviews

East Hampton Family Vacation Home

East Hampton Family Vacation Home! Located on a private street in the quiet East Hampton Springs Neighborhood. 4 Bedrooms / 4 Baths, sleeps 6 adults / 5 children. Heated saltwater pool with large surrounding patio with new pool cabana is perfect for indoor/outdoor entertaining. Gourmet kitchen, screened porch, 65 inch TV , Weber grill, bikes, fire pit, hammocks . Notes: utilities included, pool heater usage is at renters expense, $300/wk cleaning fee.

Jan. 22 – 29

$892 CAD per night

Guest favourite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Oct. 9 – 16

$1,079 CAD per night

Guest favourite

Home in Amagansett

4.92 out of 5 average rating, 13 reviews

Chic Walk to the Beach in Amagansett

Located on the idyllic Amagansett Lanes, this dream-like two bedroom, one bath home marries nature, art and design to create the ultimate, sun-filled beach getaway. Moments from the Amagansett Square and Ocean Beaches - everything you need is within walking distance, whether it be a morning coffee at Jack's Stir Brew, fresh local produce from Amber Waves Farm or a stroll along Atlantic Beach.

Apr. 17 – 24

$674 CAD per night

Guest favourite

Home in Montauk

4.91 out of 5 average rating, 415 reviews

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Dec. 7 – 14

$332 CAD per night

Guest favourite

Cottage in East Hampton

4.98 out of 5 average rating, 262 reviews

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

Jan. 21 – 28

$446 CAD per night

Guest favourite

Home in Amagansett

4.97 out of 5 average rating, 34 reviews

Wonderful Amagansett Home - Bay View & Heated Pool

Beautifully designed home located just a few minutes to ocean beaches, town & Vineyards. Heated pool, large BBQ grill , spacious living, water views and a large expansive deck are just a few of the highlights. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

May 6 – 13

$669 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Amagansett vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Amagansett's top sights

Indian Wells Beach61 locals recommend

The Stephen Talkhouse136 locals recommend

La Fondita63 locals recommend

Indian Wells Tavern20 locals recommend

Cirillos Markets Amagansett IGA51 locals recommend

Hampton Chutney Co.69 locals recommend

Other great vacation rentals in Amagansett

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 12 reviews

Historic East Hampton Home - Private Beach Access

Dec. 4 – 11

$826 CAD per night

Guest favourite

Guest suite in East Hampton

5.0 out of 5 average rating, 6 reviews

1 Bedroom Apartment with Pool in Springs

Jan. 21 – 28

$229 CAD per night

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 14 reviews

Cozy Beach Oasis in East Hampton + Pool

Oct. 3 – 10

$1,284 CAD per night

Superhost

Home in Amagansett

4.9 out of 5 average rating, 20 reviews

Classic Hamptons Cottage - Heart of Amagansett

Jan. 24 – 31

$1,023 CAD per night

Guest favourite

Cottage in Montauk

4.97 out of 5 average rating, 31 reviews

Sharkey Cottage

Sep. 2 – 9

$1,295 CAD per night

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 10 reviews

Designer East Hampton with Bay Views + Pool

Apr. 29 – May 6

$1,377 CAD per night

Guest favourite

Cottage in Sag Harbor

5.0 out of 5 average rating, 29 reviews

Luxury Gem At The Heart of Sag Harbor Village

Jun. 23 – 30

$1,216 CAD per night

Superhost

Home in East Hampton

5.0 out of 5 average rating, 5 reviews

Waterfront Oasis + Pool/Spa & Private Beach

Nov. 11 – 18

$1,492 CAD per night

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Quick stats about vacation rentals in Amagansett

Total rentals	280 properties
Rentals with a pool	180 properties have a pool
Pet-friendly rentals	110 properties allow pets
Family-friendly rentals	230 properties are a good fit for families
Total number of reviews	3.4K reviews
Nightly prices starting at	$207 CAD before taxes and fees

Vacation rentals in Amagansett

Top-rated vacation rentals in Amagansett

Home in East Hampton

Cabin in Montauk

Home in Amagansett

Home in East Hampton

Cottage in East Hampton

Home in East Hampton

Home in East Hampton

Apartment in Sag Harbor

Home in Amagansett

Home in Montauk

Cottage in East Hampton

Home in Amagansett

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Amagansett vacation rentals

Stay near Amagansett's top sights

Other great vacation rentals in Amagansett

Home in East Hampton

Guest suite in East Hampton

Home in East Hampton

Home in Amagansett

Cottage in Montauk

Home in East Hampton

Cottage in Sag Harbor

Home in East Hampton

Quick stats about vacation rentals in Amagansett

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore