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Ocean View Cottage: Yale, Beach, Wedding & Golf

The Island Sound Cottage is pet friendly, has been newly renovated (not a shared space). 15 mins to Yale & Downtown; unobstructed ocean view from the living room & balcony. Located in a beautiful and safe location. This pristine home comes with breathtaking ocean views! Head out your front door to stroll along the famous Pardee Seawall Park on The Long Island Sound. Enjoy this colonial cottage with big windows, skylights, balcony, plenty of sunlight and sunset. *Fully enclosed backyard.

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond -Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action. NOTE: Due to water leakage issues, the bath in pool house is not available

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

Duffy's On Lake Montauk 3

Recently renovated in soft blues and whites, these sleek units offer a full kitchen, washer/dryer, living area and large deck steps from Lake Montauk. Paddle boards , kayaks and beach chairs offered. All units have Bose players and Roku. The units sit at a 90 degree angle to the lake with partial lake views from the deck. The lake and beachfront are a 1 minute walk from the unit. PRICES INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAX

Hamptons Waterfront Suite | Private Hot Tub

✔ Separate private guest suite with its own entrance ✔ Entire back property exclusively yours (not shared) ✔ Year-round saltwater hot tub ✔ Private dock + 2-person kayak ✔ Fire pit, lounge chairs & beach towels ✔ Stunning waterfront sunrise & sunset views ✔ Private porch & outdoor shower ✔ 55" Smart TV & electric fireplace ✔ Self check-in & central air ✔ 19 minutes to Southampton Village ✔ Adults only – No pets – No children

4 Bedroom MTK Retreat 5 min walk to Private Beach

Spacious Montauk retreat with big fenced yard, decks, and fire pit—walk to private lifeguarded beach, restaurants, and live music. Newly renovated kitchen and floors. Sleeps 8 adults + 1 child; crib, Pack & Play, bed rails, and toddler chair available. Outdoor shower and BBQ for easy summer living. Enjoy Culloden Beach sunsets and bonfires. Perfect for families or friends looking to relax and explore. Min rental age: 30

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

Dockside 2BR - Marina - Dining - Charter Access Un

Any closer to the marina and you’d be swimming in the Atlantic. Our sweet little cottage sits right on Westlake Marina. From your front door, you can book a charter, grab a bowl of Westlake Fish House’s famous clam chowder, or walk to Gosman’s for a sundae and a sunset. Inside enjoy heated floors, plush beds, and a fully-equipped kitchen, making this a perfect place to land after all the Montauk fun.

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Center of Town + Ideal for Beach, Golf & Tennis

Our home is centrally located in Montauk. 5 minutes +/- from everywhere you want to be. Montauk Downs State Park is directly across the street, providing public access to golf, tennis, pickleball, swimming and a patio bar/grill that overlooks the golf course. Quiet neighborhood + private backyard setting. Convenience and relaxation at its finest!