Vacation rentals in Amagansett

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Top-rated vacation rentals in Amagansett

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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

Oct. 8 – 15

$462 CAD per night

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.

Feb. 3 – 10

$839 CAD per night

Guest favourite

Cottage in Montauk

4.97 out of 5 average rating, 31 reviews

Sharkey Cottage

Booking now for spring, summer & fall 2024! Lovely Sharkey waterfront, large 1BR cottage sits on a great lawn w/4 other cottages on Ft Pond Bay. Sharkey is steps away from our private beach w/ private beach path & benches, has indoor & outdoor showers, dining areas, wrap around patio, full kitchen, gas grill & is dog-friendly. A unique Montauk experience w/ quiet beach & the best sunsets in town! Walking distance to LIRR, Duryea's Lobster Deck-Market, Roberta's Pizza, Surf Lodge & The Montauket.

Oct. 3 – 10

$587 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. 28 – Oct. 5

$800 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 29 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

$780 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.

Nov. 29 – Dec. 6

$999 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. 24 – 31

$1,078 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 20 reviews

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Nov. 3 – 10

$502 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.

Jun. 20 – 27

$988 CAD per night

Guest favourite

Home in Montauk

4.91 out of 5 average rating, 416 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.

Mar. 7 – 14

$332 CAD per night

Guest favourite

Cottage in East Hampton

4.98 out of 5 average rating, 263 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).

Nov. 12 – 19

$445 CAD per night

Guest favourite

Cottage in Amagansett

4.94 out of 5 average rating, 17 reviews

Wonderful cottage in the middle of Amagansett.

Enjoy a stylish experience at this centrally-located place in the middle of Amagansett. Walk to everything, beach, restaurants, bars and farmer markets. Freshly renovated and perfect for a getaway to the beach. No car needed as its a walk to the bus and train, but on site parking is also available.

May 16 – 23

$533 CAD per night