Top 13 Hamptons Summer Weekend Rentals for Every Style

The Hamptons, a delightful group of seaside communities nestled on Long Island, New York, is the perfect spot for your summer getaways! Among these charming towns, East Hampton stands out with its beautiful beaches, fabulous dining options, and lively nightlife, making it an ideal destination for those seeking the best of what the Hamptons have to offer. Whether you want to unwind in the serene atmosphere of East Hampton or have a bit of fun exploring its vibrant social scene, you'll find a wide array of rental choices to suit your needs. Check out this carefully curated list of the top 13 summer weekend rentals in East Hampton, all designed to bring you relaxation and enjoyment! From luxurious accommodations to cozy beachside cottages, East Hampton has something for everyone looking to make the most of their summer in the Hamptons.

1. Oceanfront Oasis in Montauk

This luxurious oceanfront property boasts breathtaking views of the Atlantic Ocean. With direct beach access, it is perfect for sunbathing, swimming, and evening strolls along the shore. The sound of the waves crashing against the rocks creates a soothing soundtrack, enhancing the serene atmosphere of this coastal retreat. Imagine waking up to the gentle sea breeze and the vibrant colors of the sunrise painting the sky, setting the tone for a perfect day by the beach.

Features

• 5 bedrooms, 4 bathrooms
• Private pool and hot tub
• Spacious outdoor deck with BBQ grill

The interior boasts a lovely open-concept design that welcomes in natural light through large windows, creating a warm and inviting atmosphere. The fully equipped kitchen and elegant dining area are perfect for cozy family gatherings or entertaining friends. Each bedroom is beautifully decorated, providing a peaceful retreat with soft bedding and en-suite bathrooms that feel like a spa experience. You’ll especially love the master suite, which features a private balcony where you can enjoy your morning coffee while taking in the breathtaking ocean views.

Beyond its luxurious amenities, this property is conveniently located close to some of Montauk's best attractions. Just a short drive away, you can wander through charming local shops, savor fresh seafood at popular restaurants, or dive into outdoor adventures like surfing and hiking in the nearby state parks. Plus, the vibrant nightlife of Montauk has something for everyone – from beach bonfires to lively live music events, you'll always find something fun to enjoy during your stay!

2. Charming Cottage in Sag Harbor

This quaint cottage offers a cozy retreat with a touch of rustic charm. Located in the heart of Sag Harbor, it is just a short walk to local shops and restaurants, making it an ideal spot for those who appreciate both tranquility and convenience. The surrounding area is steeped in history, with many buildings dating back to the 19th century, providing a picturesque backdrop for your stay.

Highlights

• 2 bedrooms, 1 bathroom
• Quaint garden area
• Close proximity to the bay

With its vintage decor and comfortable furnishings, this cottage provides a warm atmosphere. Enjoy morning coffee on the porch or an evening barbecue in the garden, where you can soak in the serene surroundings. The garden is not only a perfect spot for relaxation but also features a variety of seasonal flowers and herbs, inviting you to explore your green thumb or simply enjoy the beauty of nature.

As you venture out, you'll find that Sag Harbor is a treasure trove of activities. Spend your days exploring the charming streets lined with art galleries and boutiques, or take a leisurely stroll along the waterfront, where you can watch the boats sail by. For those interested in history, the Sag Harbor Whaling and Historical Museum provides a fascinating glimpse into the town's maritime past. Whether you're seeking adventure or simply a peaceful escape, this cottage serves as the perfect home base for your Sag Harbor experience.

If you're looking to explore beyond the mainland, Shelter Island is an easy ferry ride from the Hamptons and offers a unique, laid-back atmosphere that contrasts with the hustle and bustle of other parts of the region. Known for its peaceful surroundings and unspoiled nature, Shelter Island is a haven for outdoor enthusiasts who enjoy hiking, kayaking, and biking. Renting a private home on the island allows you to experience a slower pace of life while still having easy access to the Hamptons’ best beaches, restaurants, and cultural attractions. This hidden gem is the ultimate escape for those looking to recharge and reconnect with nature.

3. Modern Villa in East Hampton

This contemporary villa is designed for those who appreciate modern aesthetics. With sleek lines and high-end finishes, it offers a luxurious stay just minutes from the beach. The architectural design seamlessly integrates indoor and outdoor spaces, allowing natural light to flood the interiors while providing stunning views of the surrounding landscape. The use of natural materials, such as wood and stone, adds warmth to the modern design, creating a welcoming atmosphere that invites relaxation and enjoyment.

Amenities

• 4 bedrooms, 3 bathrooms
• Infinity pool with ocean views
• Home theater system

This spacious living area invites you to unwind in comfort, while the gourmet kitchen is truly a chef's paradise. Equipped with top-of-the-line appliances and plenty of counter space, it inspires culinary creativity and is perfect for hosting friends. The outdoor area boasts cozy lounge furniture, creating a lovely spot for evening cocktails. Just picture yourself enjoying a refreshing drink as you watch the sunset painting the sky in beautiful shades of orange and pink. If you love cooking outdoors, you’ll appreciate the built-in barbecue grill that enhances the outdoor dining space, making every alfresco meal a delightful celebration.

4. Historic Estate in Southampton

This stunning estate combines history with modern luxury. Set on sprawling grounds, it offers a unique glimpse into the past while providing all the comforts of today. The estate's rich history is reflected in its architecture, which showcases intricate details and craftsmanship that have stood the test of time. Each room tells a story, with original features lovingly preserved alongside contemporary amenities that cater to modern living.

Unique Features

• 7 bedrooms, 6 bathrooms
• Formal gardens and tennis court
• Historic architecture with modern updates

Guests can wander through the beautifully manicured gardens or enjoy a fun game of tennis before retreating to the elegant living spaces. This lovely estate is perfect for large gatherings or sweet family reunions. Besides the main residence, the property features charming outbuildings that serve as cozy guest accommodations or private retreats. This allows visitors to enjoy their own space while still feeling connected to the larger group. The estate's expansive grounds are not only a feast for the eyes but also provide plenty of opportunities for outdoor activities, from leisurely strolls along the tree-lined paths to delightful picnics on the lush lawns. 

As evening falls, the estate transforms into a magical setting, with the gentle glow of lanterns illuminating the pathways and the soothing sounds of nature creating a serene backdrop. The spacious dining area, featuring a grand table, warmly invites guests to gather for memorable meals, where stories can be shared and laughter can fill the halls. Whether hosting a formal dinner party or a casual barbecue, the estate's versatile spaces effortlessly accommodate every occasion, making it a truly enchanting destination for relaxation and celebration.

For those who appreciate a mix of history and modern luxury, East Hampton is home to some of the most remarkable estates in the Hamptons. Whether you’re looking for a comfortable house with traditional charm or a modern architectural masterpiece, the area has plenty of vacation rental options to suit every taste. With tree-lined streets, elegant mansions, and a vibrant arts scene, this charming village offers a serene retreat that is perfect for unwinding while still being close to high-end shopping and gourmet restaurants. If you’re seeking an estate that blends classic charm with contemporary comforts, this is the perfect spot for your summer weekend escape.

5. Beach House in Amagansett

This charming beach house is perfect for families or groups looking for a laid-back atmosphere. Located just steps from the beach, it offers a relaxing getaway. The soothing sound of waves crashing against the shore and the gentle sea breeze create an idyllic setting for unwinding and reconnecting with loved ones. With its cozy interiors and inviting decor, this beach house feels like a home away from home, making it an ideal retreat for those seeking both comfort and adventure.

Family-Friendly Features

• 3 bedrooms, 2 bathrooms
• Kid-friendly amenities
• Outdoor shower

The open living area is perfect for family activities, and the outdoor space features a lovely patio for al fresco dining. With the beach just a stone's throw away, spontaneous beach days and sunset picnics are always within reach. Families can enjoy building sandcastles, collecting seashells, or simply relaxing under the warm sun. For those who love to cook, the fully equipped kitchen has everything you need to whip up fresh seafood from local markets, making mealtimes truly enjoyable. Plus, the beach house comes stocked with games and books, ensuring that evenings are filled with laughter and cherished moments together.

As the sun dips below the horizon, the outdoor patio changes into a magical gathering spot where families come together around a fire pit, roasting marshmallows and sharing stories beneath the stars. The surrounding area boasts a variety of recreational activities, from biking along picturesque trails to discovering nearby nature reserves. Whether it's a morning jog on the beach or an afternoon of kayaking in the serene waters, adventure awaits at every turn. This beach house is not just a cozy retreat; it’s a gateway to creating unforgettable memories in a stunning coastal setting.

6. Luxurious Penthouse in Bridgehampton

This penthouse offers an upscale experience with stunning views of the surrounding area. Perfect for couples or small groups, it combines luxury and comfort.

Key Features

• 2 bedrooms, 2 bathrooms
• Rooftop terrace with hot tub
• High-end appliances and furnishings

With its modern amenities and chic decor, this penthouse is an excellent choice for those looking to indulge. Enjoy evenings on the rooftop terrace, soaking in the hot tub under the stars.

7. Rustic Retreat in Water Mill

For travelers who enjoy an active getaway, East Hampton is a paradise for outdoor enthusiasts. From scenic hiking trails and biking routes to world-class fishing and beach activities, this area offers endless opportunities to explore the great outdoors. Rent a vacation rental near the shore and start your morning with a refreshing paddleboarding session before heading out to discover local parks and nature preserves. The area’s breathtaking landscapes make it an ideal destination for those who love adventure and appreciate the natural beauty of the Hamptons.

This rustic retreat offers a peaceful escape surrounded by nature. With ample outdoor space, it’s perfect for those looking to unwind and reconnect with the outdoors.

Outdoor Amenities

• 4 bedrooms, 3 bathrooms
• Large backyard with fire pit
• Access to hiking trails

The cozy interior features a fireplace and comfortable furnishings, making it a great spot for family gatherings. The outdoor fire pit is perfect for roasting marshmallows and sharing stories under the stars.

8. Elegant Manor in Westhampton Beach

This elegant manor offers a sophisticated atmosphere with luxurious amenities. Ideal for those looking to host events or family gatherings, it provides ample space and comfort.

Event-Friendly Features

• 6 bedrooms, 5 bathrooms
• Grand dining room
• Outdoor pool and cabana

The beautifully designed interior is complemented by an expansive outdoor area, perfect for hosting summer parties. The grand dining room can accommodate large dinner parties, making it a versatile choice for entertaining.

9. Cozy Bungalow in East Quogue

This cozy bungalow offers a charming and intimate setting for couples or small families. With a relaxed vibe, it’s perfect for a weekend getaway.

Comfortable Amenities

• 2 bedrooms, 1 bathroom
• Private patio with seating
• Short drive to the beach

Guests can enjoy the comfortable furnishings and inviting decor. The private patio is an excellent spot for morning coffee or evening relaxation, providing a tranquil escape.

10. Contemporary Home in Southampton

This contemporary home features modern design elements and high-end finishes. It’s perfect for those looking for a stylish and comfortable stay.

Modern Features

• 5 bedrooms, 4 bathrooms
• Smart home technology
• Heated pool

The open floor plan allows for seamless flow between the living, dining, and kitchen areas. The heated pool provides year-round enjoyment, while the outdoor lounge area is perfect for soaking up the sun.

11. Seaside Villa in Montauk

This seaside villa offers stunning ocean views and a luxurious atmosphere. Ideal for those looking to indulge in a beachside retreat, it combines comfort and elegance.

Luxury Amenities

• 4 bedrooms, 3 bathrooms
• Infinity pool overlooking the ocean
• Private beach access

The spacious living areas are designed for relaxation, while the outdoor spaces provide breathtaking views. The infinity pool is perfect for cooling off on hot summer days.

For travelers seeking a more secluded and intimate retreat, Shelter Island offers some of the most tranquil vacation rental options in the Hamptons. Whether it’s a cozy beach cottage or a sprawling waterfront estate, this amazing location provides unparalleled access to nature, local farm-to-table dining, and some of the best sunset views in the region. A private home on the island offers a true escape, where you can enjoy peaceful surroundings while taking in the amazing views of Peconic Bay. Whether you’re watching sailboats drift by or spotting wildlife in the Mashomack Preserve, Shelter Island is the perfect spot to experience the Hamptons at a slower, more relaxed pace.

12. Family-Friendly Home in Hampton Bays

This family-friendly home is designed with comfort and convenience in mind. With plenty of space for children and adults alike, it’s perfect for family vacations.

Family Amenities

• 5 bedrooms, 4 bathrooms
• Game room with pool table
• Large backyard for outdoor activities

The game room provides entertainment for all ages, while the spacious backyard is perfect for outdoor games and activities. The home’s proximity to local attractions makes it an ideal base for family adventures.

13. Luxurious Retreat in Shelter Island

This luxurious retreat offers a serene escape from the hustle and bustle of everyday life. Nestled in a quiet area, it’s perfect for those looking to unwind and recharge.

Relaxation Features

• 3 bedrooms, 2 bathrooms
• Private hot tub and sauna
• Access to nearby nature trails

With its tranquil atmosphere and luxurious amenities, this retreat is ideal for relaxation. The private hot tub and sauna provide the perfect way to unwind after a day of exploring the beautiful surroundings.

Your Perfect Hamptons Getaway Awaits

Choosing the right rental in the Hamptons can elevate a summer getaway into an unforgettable experience. Whether you’re seeking a luxurious villa, a charming cottage, or a family-friendly home, the options are plentiful. Each of these top 13 rentals offers unique features and amenities, ensuring that visitors can find the perfect place to relax, unwind, and enjoy the beauty of this iconic destination.

For an all-encompassing luxury experience, pairing a stunning vacation rental with a stay near Sunset Beach is a fantastic choice. This popular summer destination is famous for its lively atmosphere, oceanfront dining, and breathtaking sunset views. Whether you're staying in a private home with an infinity pool or a comfortable house with direct beach access, the combination of amazing views and upscale amenities ensures an unforgettable Hamptons getaway. Sunset Beach is also known for its vibrant nightlife, making it the perfect spot to relax during the day and celebrate in style after the sun sets.

To truly elevate your stay, why not add a sprinkle of adventure by chartering a private yacht with Yacht Hampton? Just picture yourself spending a glorious day cruising along the breathtaking coastline, basking in the sunshine, and savoring a delightful meal with friends and family right on the water. It’s a wonderful way to craft even more cherished memories during your getaway!

Imagine the ideal rental paired with an incredible yacht adventure—your time in the Hamptons is bound to be truly amazing! Are you ready to make waves? Dive into Yacht Hampton for all the details on how to make your summer getaway completely unforgettable!