
Holiday houses in The Hamptons
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Top-rated holiday rentals in The Hamptons
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Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Silver House: 3BR Home with Private Beach Access
Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Sag Harbor Village Cottage with Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Charming Southampton Light filled Cottage
Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

PICTURE PERFECT SOUTHAMPTON HOME-
Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Spacious East Hampton Getaway with Pool
This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

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.

Light-filled Sag Harbor village gem
Midcentury style in the heart of Sag Harbor Historic district. Soaring 20-foot floor-to-ceiling windows and skylights throughout offer the ideal indoor-outdoor experience for enjoying all seasons. Featured in Home & Garden, the house is situated on sprawling grounds, one of the largest lots in Sag Harbor. In the winter, enjoy the Scandinavian sauna and lounge in front of the fireplace. Gunite pool open May 25 to Sept 3.

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Serene 3 Bed 2.5 Bath House w/Heated Pool
Situated off a quiet lane on a half-acre, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 3 wonderful bedrooms 2 modern bathroom and a heated saltwater pool ( See Pool heat and Pool Closure Details ) with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!
Popular amenities for The Hamptons holiday rentals
Other great holiday rentals in The Hamptons

Hamptons Tiny House!

Chic Hamptons Retreat | Fireplace, Hot Tub, Beach

Storybook Cottage Seconds to East Hampton Village

The Hideaway | Clearwater Beach

The Perfect Summer Beach Home in Sag Harbor

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Cedar Hot Tub, Suana, Heated Pool walk to water

Stylish Beauty with Tennis
Frequently Asked Questions
How is the weather in The Hamptons?
The Hamptons has a temperate climate. Summers are warm, with highs around 80°F (27°C), while winters are cooler, with temperatures averaging 38°F (3°C). Spring and fall are generally mild. Remember to pack your swimsuit for the summer, and a cozy jacket for cooler evenings.
What are some of the best things to do in The Hamptons?
Popular activities in The Hamptons include sunbathing at the pristine beaches, exploring the Parrish Art Museum, and visiting the local wineries. You can also enjoy a leisurely walk around the East Hampton Windmill or take a scenic bike ride along the Montauk Point State Parkway.
What is the best time of year to visit The Hamptons?
The Hamptons is most popular in the summer, from Memorial Day to Labor Day. This is when you can enjoy events like the Hampton Classic Horse Show, the East Hampton Artists & Writers Charity Softball Game, and the Southampton August Fair.
What are the best places to stay in The Hamptons?
Popular areas to stay in The Hamptons include the vibrant towns of Southampton and East Hampton. For those seeking a more laid-back vibe, Montauk and Amagansett are often recommended. If you're looking for a mix of both, consider staying in the charming village of Sag Harbor.
What are the best places to visit in The Hamptons?
In The Hamptons, you might enjoy visiting the historic Montauk Point Lighthouse, the serene LongHouse Reserve, or the iconic Maidstone Club. You could also explore the Parrish Art Museum or take a leisurely stroll around the beautiful Elizabeth A. Morton National Wildlife Refuge.
What are some hiking trails in The Hamptons?
The Hamptons is home to several hiking trails. The Hither Hills State Park trail, the Mashomack Preserve trails on Shelter Island, and the Walking Dunes trail in Napeague are all frequently suggested. These provide opportunities to explore the beautiful natural scenery of The Hamptons.
What are some family activities to do in The Hamptons?
Families often enjoy visiting the Children's Museum of the East End, exploring the Montauk Point Lighthouse, or spending a day at Cooper's Beach. You might also consider taking a stroll around the Southampton Arts Center or exploring the fascinating exhibits at the South Fork Natural History Museum.
What are some of the best day trip ideas in The Hamptons?
Day trips from The Hamptons often include a visit to the beautiful Shelter Island, exploring the bustling town of Riverhead, or a ferry ride to Block Island. You might also consider heading to the North Fork for a change of scenery, known for its beautiful vineyards and charming farm stands.
Destinations to explore
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- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Cedar Beach
- Brownstone Adventure Sports Park
- Woodmont Beach
- Sunken Meadow State Park
- Silver Sands Beach
- Napeague Beach
- Amagansett Beach
- Jennings Beach
- Wildemere Beach
- Sandy Beach
- Seaside Beach
- Ninigret Beach
- Outer Beach at Smith Point County Park




