![]() | Beautifully refreshed cottage in Sag Harbor 47 Stoney Hill Rd | $4,000April 1-30th 2026 $19,000August 1st to Labor Day 2026 $19,000August 1-31st 2026 $4,000January 1-31st 2026 $35,000July 1st thru Labor Day 2026 $16,000July 1-31st 2026 $4,000March 1-31st 2026 $40,000Memorial Day to Labor Day 2026 $4,000November 1-30th 2026 $4,000October 1-31st 2026 $4,000September 1-30th 2026 $4,000Winter 2026 |
![]() | The LUXURY RESORT SouthamptonWebID# 2380760 June 1-30th 2026 $100,000 June-July 2026 $225,000 July 1-31st 2026 $199,000 July 1st thru Labor Day 2026 $350,000 Memorial Day to Labor Day 2026 $450,000 August 1-31st 2026 $199,000 August 1st to Labor Day 2026 $225,000 8 BR 11 bath | $225,000August 1st to Labor Day 2026 $199,000August 1-31st 2026 $350,000July 1st thru Labor Day 2026 $199,000July 1-31st 2026 $225,000June-July 2026 $100,000June 1-30th 2026 $450,000Memorial Day to Labor Day 2026 |
![]() | Newly Restored Southampton Summer Home 6 McGregor Dr | $60,000August 1st to Labor Day 2026 $50,000August 1-31st 2026 $100,000July 1st thru Labor Day 2026 $50,000July 1-31st 2026 $45,000June 1-30th 2026 $120,000Memorial Day to Labor Day 2026 $165,000Year round 2026 |
![]() | Southampton Summer Rental 4BR w Pool, Jeep Wrangler & Beach Pass 21 Kennedy Dr | $115,000April through Labor Day 2026 $19,000April through May 2026 $8,000April 1-30th 2026 $42,500August 1st to Labor Day 2026 $42,500August 1-31st 2026 $42,500July 1-31st 2026 $70,000June-July 2026 $82,000July 1st thru Labor Day 2026 $105,000May through Labor Day 2026 $90,000Memorial Day to Labor Day 2026 $8,000November 1-30th 2026 $12,000October 1-31st 2026 $15,000September 1-30th 2026 $175,000Year round 2026 $10,000May 1-31st 2026 $45,000June 1-30th 2026 |
![]() | Proven Sag Harbor Rental — Holiday Warmth, Summer Perfection 19 Tredwell Ln | $40,000August 1-31st 2026 $35,000July 1-31st 2026 |
![]() | Waterfront in Sag Harbor Village! 11 Bluff Point Rd | $40,000August 1st to Labor Day 2026 $40,000August 1-31st 2026 $75,000July 1st thru Labor Day 2026 $35,000July 1-31st 2026 $95,000Memorial Day to Labor Day 2026 $6,500April 1-30th 2026 $6,500January 1-31st 2026 $6,500March 1-31st 2026 $6,500November 1-30th 2026 |
![]() | Newly Renovated 6 Bedroom Southampton Home 106 Henry Rd | $40,000April through May 2026 $20,000April 1-30th 2026 $60,000August 1st to Labor Day 2026 $12,000January 1-31st 2026 $12,000March 1-31st 2026 $25,000May 1-31st 2026 $12,000November 1-30th 2026 $12,000October 1-31st 2026 $20,000September 1-30th 2026 $225,000Year round 2026 |
![]() | Exquisite Newly Renovated Southampton Village Home 81 Leos Ln | $30,000April 1-30th 2026 $25,000January 1-31st 2026 $375,000July 1st thru Labor Day 2026 $150,000June 1-30th 2026 $25,000March 1-31st 2026 $40,000May 1-31st 2026 $425,000Memorial Day to Labor Day 2026 $25,000November 1-30th 2026 |
![]() | Beautiful Southampton Village Retreat Pool + Tennis 298 Narrow Ln | $30,000January 1-31st 2026 $30,000March 1-31st 2026 $30,000November 1-30th 2026 $175,000August 1st to Labor Day 2026 |
![]() | Gorgeously Renovated Southampton Village Home! 241 Hill St | $125,000August 1st to Labor Day 2026 $100,000July 1-31st 2026 $50,000June 1-30th 2026 $250,000Memorial Day to Labor Day 2026 $50,000September 1-30th 2026 |
![]() | Amazing Southampton Summer Retreat! 126 Somerset Ave | $185,000August 1st to Labor Day 2026 $350,000July 1st thru Labor Day 2026 $175,000July 1-31st 2026 $235,000June-July 2026 $70,000June 1-30th 2026 $400,000Memorial Day to Labor Day 2026 $40,000April 1-30th 2026 $25,000January 1-31st 2026 $25,000March 1-31st 2026 $50,000May 1-31st 2026 $25,000November 1-30th 2026 $25,000October 1-31st 2026 $45,000September 1-30th 2026 |
![]() | Nice and Easy Summer Rental in Shinnecock Hills SouthamptonWebID# 1086530 June 1-30th 2026 $25,000 July 1-31st 2026 $22,000 July 1st thru Labor Day 2026 $50,000 Memorial Day to Labor Day 2026 $59,000 August 1st to Labor Day 2026 $29,000 September 1-30th 2026 $11,900 October 1-31st 2026 $9,800 4 BR 3½ bath | $9,800October 1-31st 2026 $11,900September 1-30th 2026 $59,000Memorial Day to Labor Day 2026 $22,000July 1-31st 2026 $50,000July 1st thru Labor Day 2026 $29,000August 1st to Labor Day 2026 $25,000June 1-30th 2026 |
![]() | Perfection on Shinnecock Bay 46 Atterbury Rd | $10,000November 1-30th 2026 $10,000October 1-31st 2026 $25,000September 1-30th 2026 $75,000July 1-31st 2026 $100,000June-July 2026 $35,000June 1-30th 2026 |
![]() | Canal Front - 4 Bedroom - Hampton Bays Southampton | $10,000September 1-30th 2026 $15,000August 1st to Labor Day 2026 $30,000July 1st thru Labor Day 2026 $15,000July 1-31st 2026 $10,000June 1-30th 2026 $40,000Memorial Day to Labor Day 2026 |
![]() | Sag Harbor Waterfront Home 27 Clearview Dr | $55,000August 1st to Labor Day 2026 $95,000July 1st thru Labor Day 2026 $50,000August 1-31st 2026 $115,000Memorial Day to Labor Day 2026 $25,000June 1-30th 2026 $45,000July 1-31st 2026 |
![]() | Water Mill -Big Blue Open Skies-Yearly Rental 896 Deerfield Rd, Water Mill | $4,500December 1-31st $4,500January 1-31st 2026 $4,500February 1-28th 2026 $4,500March 1-31st 2026 $4,500April 1-30th 2026 $16,000May 1-31st 2026 $35,000June 1-30th 2026 $30,000Short term 2026 $60,000July 1-31st 2026 $70,000August 1-31st 2026 $150,000Memorial Day to Labor Day 2026 |
![]() | Southampton Retreat 30 Rosko Ln, Southampton | $40,000October 1-31st $40,000November 1-30th $50,000December 1-31st $30,000January 1-31st 2026 $25,000February 1-28th 2026 $40,000March 1-31st 2026 $55,000April 1-30th 2026 $80,000May 1-31st 2026 $200,000June 1-30th 2026 $110,000July 1-31st 2026 $130,000August 1-31st 2026 $80,000September 1-30th 2026 |
![]() | Sagaponack Elegance with Pool and Tennis June 1-30th 2026 $150,000 July 1-31st 2026 $250,000 July 1st thru Labor Day 2026 $500,000 August 1st to Labor Day 2026 $275,000 Short term 2026 $50,000 Year round 2026 $695,000 September 1-30th 2026 $145,000 FURNISHED 8 BR 6½ bath | $150,000June 1-30th 2026 $500,000July 1st thru Labor Day 2026 $250,000July 1-31st 2026 $275,000August 1st to Labor Day 2026 $145,000September 1-30th 2026 $50,000Short term 2026 $695,000Year round 2026 |
Spacious Rental across from Beach with rooftop deck & more 23 Hedges Banks Dr | $130,000July 1st thru Labor Day 2026 | |
![]() | Gorgeous Sag Harbor Home Sag HarborWebID# 5001020 June 1-30th 2026 $35,000 July 1-31st 2026 $70,000 August 1-31st 2026 $70,000 August 1st to Labor Day 2026 $72,000 September 1-30th 2026 $20,000 October 1-31st 2026 $7,500 November 1-30th 2026 $7,500 March 1-31st 2026 $7,500 January 1-31st 2026 $7,500 April 1-30th 2026 $7,500 4 BR 3 bath | $7,500April 1-30th 2026 $72,000August 1st to Labor Day 2026 $70,000August 1-31st 2026 $7,500January 1-31st 2026 $70,000July 1-31st 2026 $35,000June 1-30th 2026 $7,500March 1-31st 2026 $7,500November 1-30th 2026 $7,500October 1-31st 2026 $20,000September 1-30th 2026 |
![]() | Southampton Waterfront Paradise! SouthamptonWebID# 4931644 July 1st thru Labor Day 2026 $120,000 August 1st to Labor Day 2026 $80,000 6 BR 6½ bath | $80,000August 1st to Labor Day 2026 $120,000July 1st thru Labor Day 2026 |
![]() | East Hampton Village Fringe East HamptonWebID# 4860076 July 1-31st 2026 $90,000 July 1st thru Labor Day 2026 $185,000 Memorial Day to Labor Day 2026 $225,000 August 1st to Labor Day 2026 $100,000 October 1-31st 2026 $45,000 November 1-30th 2026 $45,000 6 BR 4½ bath | $100,000August 1st to Labor Day 2026 $185,000July 1st thru Labor Day 2026 $90,000July 1-31st 2026 $225,000Memorial Day to Labor Day 2026 $45,000November 1-30th 2026 $45,000October 1-31st 2026 |
![]() | Tastefully decorated on the outskirts of East Hampton Village! East HamptonWebID# 4897985 August 1-31st 2026 $100,000 August 1st to Labor Day 2026 $100,000 5 BR 5½ bath | $100,000August 1st to Labor Day 2026 $100,000August 1-31st 2026 |
![]() | East Hampton Village Rental East HamptonWebID# 4786226 June 1-30th 2026 $50,000 July 1-31st 2026 $70,000 July 1st thru Labor Day 2026 $151,500 Memorial Day to Labor Day 2026 $170,000 August 1-31st 2026 $80,000 August 1st to Labor Day 2026 $80,000 September 1-30th 2026 $50,000 5 BR 5 bath | $80,000August 1st to Labor Day 2026 $80,000August 1-31st 2026 $151,500July 1st thru Labor Day 2026 $70,000July 1-31st 2026 $50,000June 1-30th 2026 $170,000Memorial Day to Labor Day 2026 $50,000September 1-30th 2026 |
![]() | Serene Seaside Summer Sanctuary in Amagansett 40 Bluff Rd | $150,000Memorial Day to Labor Day |
![]() | Bridgehampton Perfect Hamptons Getaway and More BridgehamptonWebID# 4887994 August 1st to Labor Day 2026 $69,500 4 BR 3 bath | $69,500August 1st to Labor Day 2026 |
Ocean Views, Beach Access, Designer Hither Hills House 46 Edison Dr | $315,000Memorial Day to Labor Day 2026 $170,000June-July 2026 $75,000June 1-30th 2026 $220,000July 1st thru Labor Day 2026 $95,000July 1-31st 2026 $145,000August 1st to Labor Day 2026 $130,000August 1-31st 2026 $15,000January 1-31st 2026 $15,000February 1-28th 2026 $15,000March 1-31st 2026 $50,000April through May 2026 $15,000April 1-30th 2026 $40,000May 1-31st 2026 $55,000September 1-30th 2026 $18,000October 1-31st 2026 $18,000November 1-30th 2026 $18,000December 1-31st 2026 $450,000Year round 2026 | |
Designer Waterfront Cottage 144 Gerard Dr | $15,000November 1-30th 2026 $15,000December 1-31st 2026 $285,000Year round 2026 $175,000Memorial Day to Labor Day 2026 $95,000June-July 2026 $45,000June 1-30th 2026 $60,000July 1-31st 2026 $100,000August 1st to Labor Day 2026 $90,000August 1-31st 2026 $12,000January 1-31st 2026 $12,000February 1-28th 2026 $12,000March 1-31st 2026 $15,000April 1-30th 2026 $25,000May 1-31st 2026 $40,000September 1-30th 2026 $15,000October 1-31st 2026 | |
![]() | Refined Restoration in Southampton Village - 6 Bed With Pool 305 North Main St | $145,000July 1st thru Labor Day 2026 $200,000Memorial Day to Labor Day 2026 $50,000June 1-30th 2026 $75,000July 1-31st 2026 $80,000August 1-31st 2026 $75,000August 1-31st 2026 |
![]() | Stunning Estate:Luxury Living Just Minutes from the Ocean! 108 Fairfield Pond Ln | $275,000August 1st to Labor Day |
![]() | Sleek & Chic on the Beach 2 Mitchell Dunes Ln | $250,000Memorial Day to Labor Day $200,000July 1st thru Labor Day $100,000July 1-31st $100,000August 1st to Labor Day $25,000Short term |
![]() | Southampton Summer or Year Round Rental Close to Village & Beach 16 Kings Ln | $75,000July 1st thru Labor Day $96,000Year round $15,000September 1-30th |
![]() | 5 BR 4 bath | $65,000August 1st to Labor Day |
![]() | East Hampton Village Fringe East HamptonWebID# 4893002 June 1-30th 2026 $20,000 July 1-31st 2026 $55,000 Memorial Day to Labor Day 2026 $130,000 August 1-31st 2026 $65,000 September 1-30th 2026 $20,000 October 1-31st 2026 $10,000 November 1-30th 2026 $10,000 4 BR 4 bath | $65,000August 1-31st 2026 $55,000July 1-31st 2026 $20,000June 1-30th 2026 $130,000Memorial Day to Labor Day 2026 $10,000November 1-30th 2026 $10,000October 1-31st 2026 $20,000September 1-30th 2026 |
![]() | Southampton New Construction with Pool House 264 S Magee St | $85,000August 1-31st $25,000September 1-30th $85,000July 1-31st $190,000July 1st thru Labor Day $290,000Year round |
![]() | Sagaponack 4BD/4BA. 1.2mi to beach w/ Pool House 5 Ranch Ct, Sagponack, NY 11962 | $105,000August 1-31st $110,000August 1st to Labor Day $22,500September 1-30th $20,000October 1-31st $13,500November 1-30th $13,500December 1-31st $12,500January 1-31st $12,500February 1-28th $12,500March 1-31st $15,000April 1-30th $17,500May 1-31st $35,000June 1-30th $95,000July 1-31st $205,000Memorial Day to Labor Day $215,000Extended season $220,000Year round $215,000April through Labor Day $30,000April through May $210,000May through Labor Day |
| 1031 found | ||