Beachfront holiday rentals in Sag Harbor

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Incredible 2 Bedroom Waterfront Cottage!

An amazing & unique experience on the North Fork of Long Island. Sitting on a bluff 15’ above our private beach, this 3 season multi-family property boasts panoramic views of the LI Sound. Amazing sunset/sunrise views, fishing, beach combing, swimming, wineries, restaurants, shopping. Huge 2nd story deck for evening cocktails. Full kitchen, BBQ, loads of amenities. Updated inside & out. Private beach shared only with other guests of the property Please note there is some noise from passing cars

White Beach House

This clean, bright, and airy cottage offers a serene escape with stunning views of Napeague Harbor. Just a short walk away lies one of the most beautiful ocean beaches The home feature- 3 comfortable bedrooms & 3 full bathrooms and an outdoor shower Inside, The cottage is well-appointed and designed. While the train from Amagansett to Montauk does pass behind the house, it does not obstruct the tranquil bay views. Please note: Due to health concerns, we are unable to accommodate animals.

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

LoveCedarPt - Explore the Hamptons & Montauk, Eat, Provision and Glamp in Comfort at the 607 acre Cedar Point County Park on Northwest Harbor near Sag Harbor & E. Hampton. Lodge overnight in comfort & style in our furnished platform Safari Tents in a perfect tree meadow on the bluffs overlooking the bay and Shelter Island with sunsets 2nd to none. For 2025, we have 16 tents with queen beds and linens. Tents are covered with large rain flies that make a covered porch for the Adiron

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.

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Renovated Oceanfront Montauk Studio Retreat

Experience the ultimate Montauk getaway in this stylish, renovated oceanfront studio. Perched on the 2nd floor, your private balcony offers front row seats to the Atlantic-keep your eyes peeled for dolphins and whales which are frequently spotted right from the unit! Whether you're grabbing a lobster roll from the award winning food truck, dipping into the indoor pool or ending your night with a private bonfire on the beach, this is the perfect place for your east end escape.

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

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

Historic Home + Private Waterfront Access

A rare piece of East Hampton architectural history. Designed in 1958 by Kaneji Domoto, a student of Frank Lloyd Wright, this mid-century home celebrates indoor-outdoor living with walls of glass, abundant natural light, and panoramic views of Three Mile Harbor. Set among mature trees with a private staircase down to the water, the home offers a truly unique Hamptons experience - from sunrise coffees to unforgettable sunsets.