Vacation rentals in Shinnecock Hills

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Top-rated vacation rentals in Shinnecock Hills

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Guest favourite

Guest suite in Hampton Bays

4.98 out of 5 average rating, 315 reviews

CHARMING OCEAN BUNGALOW

My ocean Bungalow is super well located in Hampton Bays. You will be 10 minutes away from the center of town where the Hampton Bays train station is. You also have Starbucks, Ride Aid, king Kullen, and great eateries at your fingertips. You will also have another two great supermarkets; Stop&Shop and Wild by Nature natural food store. You will be staying in a room with a feeling of a Junior Suite with approximately 400sq feet, a much larger area than a standard room. It has an attached small full bathroom, a living space that I call “home theater” with a 75” smart TV, a wet Bar with Coffee, Expresso and Tea, your own refrigerator. No heavy cooking is allowed indoors but I will offer a grill outside, for the most gastronomically inclined guests ... there’s no dining area but you are more welcome to use the dining table at the outdoor stone patio. One of the nicest thing about our location is that we are 5 minutes from Ponquogue Beach with excellent near by restaurants such as Oklands, Sundays on the Bay, on Beach Road and Dockers waterside on Dune Road. Meschutt beach is also a great location with live music throughout the summer, not a beach for surfers or adventure swimmers, since it’s on Peconic Bay, but on a plus side, there’s a full outdoor bar for adults, I love their Rum punch, and a full service snack bar, and a gift shop that sells beach gear... etc.

Oct. 27 – Nov. 3

$406 CAD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 20 reviews

Modern Southampton home, heated pool, pickleball

A modern style and freshly renovated Southampton home with waterfront views. 5 minutes from Southampton village & Coopers Beach. The house features 5 bedrooms, 4 bathrooms, including 2 ensuites. Brand-new kitchen with large Restoration Hardware dining table that seats 12 (+8 around the oversized counter). Expertly styled. Two fireplaces. Perfect for couples and/or families (equipped with 2 cribs, pack and play,xl playpen,toys,high chair). Total beach vibes with a heated pool and new patio area.

Oct. 26 – Nov. 2

$1,328 CAD per night

Guest favourite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

May 5 – 12

$510 CAD per night

Guest favourite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Aug. 28 – Sep. 4

$595 CAD per night

Guest favourite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Sep. 21 – 28

$502 CAD per night

Guest favourite

Vacation home in Southampton

4.98 out of 5 average rating, 41 reviews

5BR, Luxury Home, Pool, Yard Close to Beach & Town

Magnificent Renovated 4,416 sq ft. Contemporary on .67 acre has 5 bedrooms 5 full bathrooms Enter into light filled living areas, faulted ceiling , fireplace with stone , white panel wainscoting and eat in kitchen with island seating , stainless steel appliances and door to a wrap around rear deck. A family room has French Doors , Bar , to the pool and expansive backyard. The beautifully appointed master suite features a vaulted ceiling in the bedroom, walk in closets & Luxe bath.

Jan. 22 – 29

$1,281 CAD per night

Guest favourite

Apartment in Hampton Bays

4.97 out of 5 average rating, 340 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Sep. 30 – Oct. 7

$407 CAD per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 34 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

Apr. 18 – 25

$1,273 CAD per night

Guest favourite

Home in Southampton

4.91 out of 5 average rating, 179 reviews

Peaceful Hamptons Cottage

Looking for a getaway? Nestled into one of the largest preserves in the Hamptons, this sunny newly renovated beachy cottage is the perfect retreat. The legendary Hamptons beaches, wineries, Southampton Village, and the world famous golf courses are less than a 10 minute drive away. There are many nearby essential shops, farm stands & restaurants. Set up for WFH with hi-speed wifi and a desk. Abuts a large nature preserve with hiking paths. Lots of deer will roam by your window!

Jul. 14 – 21

$904 CAD per night

Guest favourite

Apartment in Hampton Bays

4.98 out of 5 average rating, 82 reviews

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

Nov. 12 – 19

$366 CAD per night

Guest favourite

Apartment in Southampton

4.96 out of 5 average rating, 165 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Jun. 30 – Jul. 7

$713 CAD per night

Guest favourite

Guest suite in Cutchogue

4.88 out of 5 average rating, 586 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Oct. 15 – 22

$248 CAD per night