Holiday rentals in Eastport

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Top-rated holiday rentals in Eastport

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A two-story blue house is set in a well-maintained yard with green grass and neatly trimmed hedges. A double garage doors are visible on the left, and a front porch with steps leads to the main entrance, framed by decorative shrubs.
Home in Center Moriches
4.92 out of 5 average rating, 52 reviews

Peaceful and Bright 4 Bedroom Getaway Home

Come relax with your family in our quiet and peaceful home at any time of the year! It is your quick getaway from city/work life. Each room is spacious and the kitchen is open and welcoming for our special guests. In the backyard is a fire pit and a canal that leads out to the bay of the South Shore of the Long Island Sound. You can enjoy our patio with a beautiful view. Our bathrooms are newly renovated. Brookhaven beach/playground access is a five minute drive away. We hope you can enjoy!

Guest favourite
A bright and airy living space features a cozy beige sofa facing large windows with water views. A staircase leads to the upper level, and natural light illuminates the open layout. Light-colored furniture and decorative accents create a relaxing coastal ambiance.
Home in Westhampton Beach
4.97 out of 5 average rating, 38 reviews

Magnificent Bayfront Retreat

Welcome to the Hamptons! The view from this home, that sits right on the water, boasts the most beautiful sunsets that need to be seen to be believed. Whether you’re spending the day in the sun on the beach (a short 5 minute walk), grilling on the deck watching the sunset over the bay, soaking in the hot tub, fishing on the private dock, or lounging on the couch watching a movie on our 75 inch TV after a day of fun in the sun, this home is a perfect getaway for you, your family, and friends!

Top guest favourite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck
4.93 out of 5 average rating, 134 reviews

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Top guest favourite
Home in Mastic
4.98 out of 5 average rating, 66 reviews

Modern Hamptons Home

Escape to a beautifully renovated Hamptons retreat designed for comfort, privacy, and effortless outdoor living. Enjoy a spacious deck and private fenced backyard featuring a unique outdoor lounge, BBQ grill, fire pit, and refreshing outdoor shower. Inside, bright and stylish spaces offer all the comforts of home. Perfect for relaxing, dining outdoors, and creating memorable moments with family and friends, all while being conveniently located near beaches, restaurants, shopping, and local.

Guest favourite
The image captures a spacious outdoor area featuring a large, heated swimming pool surrounded by lounge chairs. A well-maintained lawn is visible, along with a charming cottage that includes an inviting porch. Lush greenery and trees form a serene backdrop.
Cottage in Remsenburg - Speonk
4.98 out of 5 average rating, 40 reviews

Newly built cottage near the bay and hamptons

Kick back and relax by the amazing pool in this calm, newly built stylish space hosted by a super host! In the estate area of Remsenburg ten minutes from Westhampton Beach Main Street and fifteen minutes from several beaches. At the end of a private road across from the Moriches bay. Wonderful area to bike and walk. Tour options available and include sunset cruising, fishing, etc. Inquire within! Vineyards about 40 minutes away. Exclusive access to 1300 square foot cottage. 2 bed/2 bath!

Top guest favourite
A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.
Cottage in Riverhead
4.98 out of 5 average rating, 182 reviews

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.

Guest favourite
Home in Mastic
4.96 out of 5 average rating, 184 reviews

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Top guest favourite
Home in Westhampton
5.0 out of 5 average rating, 22 reviews

Chic Hamptons Gateway | Pool, Hot Tub, Beach

Stylish & airy Hamptons retreat on over an acre, minutes to ocean beaches and Westhampton Village. Thoughtfully designed, this home features 4 bedrooms, 3 full baths, and a modern open layout across 2 floors. Outside, a heated pool, hot tub and fully fenced yard offer space to unwind in privacy. Clean design, abundant natural light, seamless indoor-outdoor flow, and a calm vibe make this home ideal for an escape. Enjoy peaceful mornings, beach walks, and cozy nights by the fireplace.

Guest favourite
A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.
Home in Mastic
4.87 out of 5 average rating, 149 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favourite
A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.
Home in Hampton Bays
4.87 out of 5 average rating, 137 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will open May 23, 2026 and close on Labor Day.

Superhost
A spacious room features a queen-size bed adorned with a light gray quilt. Bedside tables with lamps flank either side, and a decorative bench sits at the foot of the bed. Natural light filters through the sheer curtains, enhancing the calming color palette.
Flat in North Fork
4.93 out of 5 average rating, 152 reviews

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

Guest favourite
A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.
Home in Westhampton Beach
4.98 out of 5 average rating, 173 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Popular amenities for Eastport holiday rentals