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129 Houses

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Hilltop Haven in Montauk with Heated Pool perfect for Families

Montauk house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Heated pool Private pool Fishing Golf course on site or within 15 min walk

All filters match

Price per night from

$687

These homes match some but not all of your filters. Clear all filters

2 of 4 match: Fishing, Private pool, Golf course on site or within 15 min walk, Heated pool

2 of 4 filters match

Price per night from

$172

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

3 of 4 filters match

Price per night from

$2,519

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$3,272

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$1,309

Abigail ‘s Nest

Brimfield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

3 of 4 match: Heated pool, Fishing, Golf course on site or within 15 min walk, Private pool

3 of 4 filters match

Price per night from

$1,031

Elegance,Privacy, French Farm House

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$1,088

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$1,374

BEAUTIFUL AND PEACEFUL RESORT-LIKE SPLIT LEVEL HOUSE FOR NON-SMOKERS ONLY

Worcester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$172

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$2,521

5 bedroom Private Family Get Away

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$1,374

Montauk Oceanfront Estate

Montauk manor house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$17,175

Magnificent private Southampton Estate

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$5,153

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$985

Exquisite Hamptons Mansion Retreat

Water Mill house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$628

New Reno Westhampton Beach Heated Pool Steps to Town

Westhampton Beach house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 16

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,428

Heated Pool 6+ Bedrooms , 4.5 BA

Noyack house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,719

Boutique Waterfront Home with Pool in Heart of North Fork

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$430

East Hampton Charming Cottage South Of the Highway Near Ocean/ Further Lane

East Hampton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,918

Village traditional on a quiet cul de sac

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,276

Greenport Beach House

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$916

Beautiful Bridgehampton Home

Bridgehampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,718

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 4 match: Heated pool, Private pool, Fishing, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$974

Chic 3 Bed Cottage w/Modern Pool, 5 Mins from Town

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$657

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$1,145

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$3,272

Luxury Oceanfront House, Pool+Jacuzzi facing the ocean, call for Deals!

Westhampton Beach house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$1,500

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$573

Elegant Meadowbrook Estate for Family Gatherings, Retreats and Special Events

Marlborough manor house

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 22

3 of 4 match: Golf course on site or within 15 min walk, Fishing, Heated pool, Private pool

3 of 4 filters match

Price per night from

$4,122

Artist get away

Southbridge apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Private pool, Fishing, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$172

2 of 4 match: Heated pool, Private pool, Fishing, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$1,260

Brand new, Hamptons beach house w/gunite pool & spa

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$2,055

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$342

Family Vacation Home, heated pool

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,254

Airy, Woodsy, Walk to Beach, New Saltwater Pool!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,064

Amagansett w/pool last two weeks of August

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$1,603

Coastal Haven: Private Pool, Bay Access, Water Sports

Aquebogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$370

Modern North Fork Haven: Beachfront,Private Pool

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 17 minutes

2 of 4 match: Fishing, Golf course on site or within 15 min walk, Heated pool, Private pool

2 of 4 filters match

Price per night from

$842

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