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
An aerial view captures the serene neighborhood, showcasing small homes interspersed with trees and greenery. The bay can be seen in the distance, along with the nearby beach access. The well-maintained grounds of the property highlight a clean, welcoming environment.
Home in Shirley
4.94 out of 5 average rating, 205 reviews

Waterview Beach House: 3 Kings + Putting Green

Unwind at this 3-story waterview beach home in Shirley, NY. Bellport Bay is right across the street with easy beach access. 0.4 mi to Shirley Beach 1.8 mi to Smith Point Beach — perfect for ocean days or Fire Island trips. Featuring: • 3 king beds + 1 full + 3 sofa beds • 70” living room TV + 3x 50” bedroom TVs • Fully equipped kitchen • BBQ grill, fire pit & putting green on premium turf • 6 beach chairs + 2 umbrellas included • High-speed WiFi & keyless entry Your Long Island beach escape!

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, 53 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!

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, 136 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
4.99 out of 5 average rating, 67 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.

Top guest favourite
A contemporary home with large windows overlooks a serene pool area. Lush greenery surrounds the property, providing a natural backdrop. Sun loungers are positioned beside the pool on spacious stone decking, inviting relaxation and outdoor enjoyment.
Home in Westhampton Beach
4.94 out of 5 average rating, 144 reviews

Hamptons Oasis: pool, grill, lush landscape

Kick back and relax in this calm, stylish, contemporary masterpiece. 4 beds, 3 baths, eco pool, and expansive outdoor living space. Architecturally impressive structure surrounded by lush landscape and tastefully decorated. The outdoor space includes a pool, a new outdoor grill, a fire pit, pool lounge chairs, a dining table under a wisteria pergola and an outdoor sofa area big enough to fit your entire party. Fully equipped kitchen. Short drive to the beach and to downtown Westhampton.

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

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, 150 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

Top guest favourite
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, 153 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!

Top guest favourite
A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.
Home in Westhampton Beach
4.93 out of 5 average rating, 165 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

Top guest favourite
Home in Remsenburg - Speonk
5.0 out of 5 average rating, 20 reviews

Westhampton Retreat to the Woods

Newly renovated 3-bedroom, 2-bath home on 1.5 private acres just minutes from the beach. Features an open kitchen, two new bathrooms, and modern finishes. Outdoors, enjoy a hammock lounge, al fresco dining, outdoor shower, and expansive grounds. The highlight: a heated saltwater pool kept at 80°. Perfect for family, friends, or a romantic Hamptons getaway. Pool is open from Memorial Day until late September, d pending on weather conditions.

Popular amenities for Eastport holiday rentals