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Top-rated vacation rentals in Southampton

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1 kati ya kurasa 2

Vila huko East Hampton

Skimhampton Road

The sounds of the city are miles away at this tranquil beach cottage. Exposed brick, creamy white walls, and glossy hardwood flooring detail a cozy atmosphere. Skylights punctuate the soaring ceilings and rows of elongated windows bathe the living space in a blanket of natural light. Drive 2 minutes to Amagansett where luxury boutiques, fine dining, and fitness classes satisfy every excursion. Plump couches invite you to sit down for a morning coffee while embracing the silence of the country. Fragrant rose bushes and dense shrubbery line the perimeter, giving you a sense of total privacy. Feel the fresh grass tickle your feet as you walk across the manicured lawn. A gunite saltwater pool is a refreshing option on summer scorchers, followed by the hot tub which will soak away your stress. When the sun sets, why not gather around the roaring patio fireplace? East Hampton Main Beach is a short, scenic route away where you’ll find a snack bar, gently rolling waves, and endlessly stretching shoreline. Visit a museum or winery in Sag Harbor, settle in at a small town café in Bridgehampton, or tee off at Sag Harbor Golf Course. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Master: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Walk-in closet, Fireplace, Television, Direct access to patio • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Walk-in closet, Lounge area • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 4: King size bed, Shared access to hallway bathroom with bedroom 5, Shower/bathtub combo, Dual vanity, Television • Bedroom 5: 2 Twin size beds, Shared access to hallway bathroom with bedroom 4, Shower/bathtub combo, Dual vanity, Television • Bedroom 6: 2 Twin size beds, Access to hallway bathroom with stand-alone shower, Dual vanity, Walk-in closet Additional bedding: • Bunk room: 2 Twin over double size bunk beds, Access to hallway bathroom with stand-alone shower, Dual vanity OUTDOOR FEATURES • Swimming pool - seasonal availability, heating included • Hot tub - seasonal availability, heating included • Chess set • Security cameras - outward facing • More under “What this place offers” below STAFF & SERVICES Extra cost (advance notice may be required): • Laundry service • More under “Add-on services” below LOCATION Points of Interest • 2 minute drive to Amagansett • 3 minute minute drive to East Hampton • 7.4 miles to Sag Harbor Golf Course • 8.2 miles to Bridgehampton • 8.5 miles to Sag Harbor Beach Access • 7 minute drive to East Hampton Main Beach • 8.3 miles to Havens Beach • 11 miles to Foster Memorial Town Beach Airport • 5.7 miles to East Hampton Airport (HTO) • 30 miles to Francis S. Gabreski Airport (FOK) • 94 miles to John F. Kennedy International Airport (JFK)

Okt 31 – Nov 7

$3,000 kwa usiku

Vila huko East Hampton

Ukadiriaji wa wastani wa 4.94 kati ya 5, tathmini 17

Chic Modern Oasis

Lush, green, and private, this modern oasis connects you to nature. Impeccably decorated, the serene estate recently underwent a renovation that left the interior with a sleek, natural palette, textured accent rugs, artful fixtures, and soft wooden décor. Located in the heart of East Hampton, you’re just a short 5-minute drive away from town where you’ll find beaches, lakes, and verdant vineyards. A multitude of windows set the interior ablaze during the brightest times of day, exuding a light and airy atmosphere. Flowing common spaces connect to the rest of the home; there are plenty of seating areas to gather around with the whole crew or to intimately converse in a small group. Sumptuous, sugar-white sofas invite you to take a seat in front of the roaring living room fireplace—perhaps with a cup of hot cocoa in hand? From the mahogany deck, stroll down the landscaped backyard to reach the heated saltwater pool. The 2-acre property features its own trails that wind their way through a dense forest. Endless beach shorelines, swaying ocean tides, and a lush nature reserve are less than 2 miles north; a tranquil walk or jog from the house. Rent a bike in nearby Amagansett and cycle around to various museums, parks, and squares. A trip to Sag Harbor will complete your stay with a selection of seaside restaurants serving the freshest fare and local wines. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM First floor • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television • Bedroom 2: Queen size bed, Ensuite bathroom with shower/bathtub combo, Television • Bedroom 3: 3 Twin size beds, Ensuite bathroom with stand-alone shower Ground floor • Bedroom 4: Queen size bed, Access to hallway bathroom with stand-alone shower, Television, Private balcony • Bedroom 5: Double size bed, Twin size bed, Access to hallway bathroom with stand-alone shower, Television Additional Bedding • Spare Room: Sofa bed OUTDOOR FEATURES • Terrace • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Des 20–27

$2,500 kwa usiku

Vila huko Southampton

Southampton Historic

An ideal location in the Arts Village neighborhood, this home is close to everything you want on your low-key retreat to the Hamptons. The quaint Tudor house, built circa 1892, has been extensively renovated. Leafy, towering trees frame the secluded property, ensuring a lavish sense of privacy. Visit a sprawling vineyard in Sag Harbor or head to the gently lapping ocean for an instant refresh. Throughout the 4,000 square feet of living area, a nostalgic dichotomy is created between original, antique detailing and contemporary upgrades. Art punctuates each room alongside décor sourced from Cuban flea markets. Exposed timber beam ceilings establish a lofty ambiance while dark hardwood floors circulate beneath intricately woven Turkish rugs. Natural light trickles in through an abundance of leaded glass windows, illuminating the open, flowing space. Seafood can be seared on the outdoor barbecue and served alfresco. The crackling wood-burning fireplace, framed by white-painted bricks, sits beneath a metallic Paul Morehouse sculpture—a focal point of the living room. Stargazing is serene from the bubbling comfort of the frothing hot tub. Main Street, the heart of Southampton, is within walking distance with posh boutiques, stimulating galleries, and a variety of restaurants serving fresh, palatable cuisine await. A short 3-minute drive and you’ll land yourself at Shinnecock Hills Golf Club. For a dose of sand and surf, Cooper's, Meschutt, and Little Plains beaches are nearby. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Walk-in closet, Television • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone rain shower • Bedroom 3: Double size bed, Ensuite bathroom with shower/bathtub combo • Bedroom 4: 2 Twin size beds, Access to hallway bathroom with stand-alone shower Additional Bedding • Spare Room: Queen size bed • More under “What this place offers” below FEATURES & AMENITIES • Nest thermometers Extra cost (advance notice may be required): • Activities & excursions • More under “Add-on services” below

Feb 15–22

$4,600 kwa usiku

Vila huko Amagansett

Amagansett Beach Home

Totally renovated 6 bedroom, 7.5 bathroom house with newly built outdoor amenities including a 46 ft long pool, an in-pool hot tub / spa, a Finnish sauna, a huge outdoor kitchen and bar area that includes an ice maker, dishwasher, sink with hot water, Green Egg grill, refrigerator and a 48" propane grill. Inside the main home, you will find indoor / outdoor spaces under a covered 500 sq porch, a chef's kitchen, a wet bar with an ice maker, 3 dedicated workspaces, a gym, and a movie theater.

Des 29 – Jan 5

$5,000 kwa usiku

Ukurasa wa mwanzo huko Sagaponack

Designer's Hamptons Stunner

A stunning retreat in Sagaponack, situated on 2.8 acres. Designed by renowned architect Robert A.M. Stern, and owned by a celebrated interior designer, the home exudes comfort & style, with access to East Hampton, Sag Harbor, and gorgeous ocean beaches. Hosting capabilities with connecting dining room and living room with fireplace, and expansive screened-in porch. The home features immaculately designed interiors, and outside are sprawling lawns, a large heated pool & spa, and tennis court.

Jan 17–24

$765 kwa usiku

Ukurasa wa mwanzo huko Sag Harbor

Home in Sag Harbor Village

‘Captains’ House located in Sag Harbor village. Beautiful home includes a large kitchen, dining rm, powder rm & 2 living rms w/ fireplace. 4 bedrooms ensuite. Separate apt w/ bedroom, living rm, kitchen, 2 baths & separate entrance. Yard is beautifully landscaped w/ a heated pool/ spa, outdoor kitchen/dining area, fire-pit & pool house w/ bathroom. House is located on Main St. edge of town. Walk to marina, cinema, theatre, museums, shopping & best restaurants in the Hamptons.

Ago 31 – Sep 7

$3,771 kwa usiku

Ukurasa wa mwanzo huko Amagansett

21 House at The Reform Club

The 21 House is a luxurious, immaculate four-bedroom private home. It is set on a serene, well-manicured private property on the grounds of The Reform Club. This sprawling residence features four king Duxiana beds, four private en-suite bathrooms and two powder rooms, four fireplaces, elegant dining room, spacious living room, full gourmet chef’s kitchen, outdoor dining areas and spa treatment room with a grand Michelangelo marble bathtub.

Ago 14–21

$7,392 kwa usiku