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Results: 43 Rentals

  • Private guest apartment close to beach with pool & tennis
    From $362 per night (USD)

    VRBO

    Private guest apartment close to beach with pool & tennis

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Sun filled guest apartment in Water Mill/ Southampton minutes from Flying Point Beach, Parrish Art Museum, Duck Walk Vin ...

    From $362 per night (USD)

    VRBO

    Details
  • Updated farmhouse with pool house, close to everything. Winter rental available.
    From $771 per night (USD)

    VRBO

    Updated farmhouse with pool house, close to everything. Winter rental available.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    7

    Prefer a couple or small family. Available for the full winter only - out by Memorial Day. A rare find - fully renovat ...

    From $771 per night (USD)

    VRBO

    Details
  • Dreaming of summer fun or an off-season adventure? Enjoy both!
    From $1020 per night (USD)

    VRBO

    Dreaming of summer fun or an off-season adventure? Enjoy both!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Book for summer fun or have an incredible off-season experience! Stunning Flying Point and Scott Cameron beaches + charm ...

    From $1020 per night (USD)

    VRBO

    Details
  • Swim in a sea of hydrangeas on this peaceful, bucolic property.
    From $1714 per night (USD)

    VRBO

    Swim in a sea of hydrangeas on this peaceful, bucolic property.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Enjoy this comfortable cottage traditional, with an open floor plan, in a bucolic setting that is surrounded by nearby f ...

    From $1714 per night (USD)

    VRBO

    Details
  • Centrally Located Southampton \/ Water Mill <br>Bright, Open Floor, Saltwater Pool
    From $1590 per night (USD)

    VRBO

    Centrally Located Southampton \/ Water Mill <br>Bright, Open Floor, Saltwater Pool

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    4 bedrooms. 3 1/2 baths, Master Bedroom on first floor (Sleeps 8). Master has a king size bed. Relaxing, Spacious, Br ...

    From $1590 per night (USD)

    VRBO

    Details
  • Historical Bed and breakfast<br>
    From $4078 per night (USD)

    Expedia

    Historical Bed and breakfast<br>

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Built in 1690, newly restored. Located in Watermill the center of the Hamptons. Restaurants and shopping right around th ...

    From $4078 per night (USD)

    Expedia

    Details
  • Beautiful cottage on meticulously maintained lawn, surrounded by...
    From $472 per night (USD)

    VRBO

    Beautiful cottage on meticulously maintained lawn, surrounded by...

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Quaint Water Mill Cottage Beautiful cottage on meticulously maintained lawn, surrounded by perennials, large deck, and ...

    From $472 per night (USD)

    VRBO

    Details
  • Charming Modern Home - Winter and Summer Retreat
    From $900 per night (USD)

    Expedia

    Charming Modern Home - Winter and Summer Retreat

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    9

    Beautiful home on a quiet street. Immaculately maintained. Summer and winter retreat. In addition to five bedrooms and t ...

    From $900 per night (USD)

    Expedia

    Details
  • New To Market Farm House in Water Mill
    Click For Pricing

    VRBO

    New To Market Farm House in Water Mill

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    This home, adjacent to a 105 acre reserve and featuring gorgeous sunsets, offers a first floor open floor plan with larg ...

    Click For Pricing

    VRBO

    Details
  • Hamptons - South of the highway - Prime Water Mill Rental
    From $2607 per night (USD)

    VRBO

    Hamptons - South of the highway - Prime Water Mill Rental

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    South of the highway - Water Mill - 2022 Rental. This former 1800s Parsonage House is located on 1.09 acres in prime Wat ...

    From $2607 per night (USD)

    VRBO

    Details
  • Spacious and Conveniently Located Home in Southampton \/ Water Mill
    From $2326 per night (USD)

    VRBO

    Spacious and Conveniently Located Home in Southampton \/ Water Mill

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Amazing location and home in the heart of Water Mill. 3 min from ocean beaches (Cooper's and Flying Point), 3 min from S ...

    From $2326 per night (USD)

    VRBO

    Details
  • SOUTH OF THE HIGHWAY DREAM!
    From $1938 per night (USD)

    Expedia

    SOUTH OF THE HIGHWAY DREAM!

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    FULL SUMMER PRICING *June 37k *July 50k *Aug - Labor Day $55K. - RENTED *WEEKLY -$13,000 per week with 2 week minimum. ...

    From $1938 per night (USD)

    Expedia

    Details
  • Exceptional Southampton Waterfront: The Mecox-Fenwick House
    From $3512 per night (USD)

    VRBO

    Exceptional Southampton Waterfront: The Mecox-Fenwick House

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Created by architect Robert Barnes, Fenwick House is situated directly on Mecox Bay in the historic Southampton hamlet o ...

    From $3512 per night (USD)

    VRBO

    Details
  • COVETED Millfarm Lane -3 min to Southampton
    From $1860 per night (USD)

    VRBO

    COVETED Millfarm Lane -3 min to Southampton

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Modern, spacious, clean , professionally decorated family home w farm views on the border of Watermill / Southampton. HO ...

    From $1860 per night (USD)

    VRBO

    Details
  • Classic Farm House in the heart of Water Mill, 2.7mi To Beach
    From $1658 per night (USD)

    VRBO

    Classic Farm House in the heart of Water Mill, 2.7mi To Beach

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy this charming 4 bedroom, 2.5 bath, dutch colonial farm house with NEWLY RENOVATED POOL HOUSE, complete kitchen, pa ...

    From $1658 per night (USD)

    VRBO

    Details
  • 12,000 sq ft of Luxury, Modern Design, Full Gym, Indoor and Outdoor Dining...
    From $28167 per night (USD)

    VRBO

    12,000 sq ft of Luxury, Modern Design, Full Gym, Indoor and Outdoor Dining...

    Bedrooms:
    10
    Bathrooms:
    8
    Sleeps:
    6

    Please note that a reservation for this property needs to be approved before it is confirmed. Cobb Road Daydream 12,00 ...

    From $28167 per night (USD)

    VRBO

    Details
  • Spectacular Vineyard Setting in Watermill
    Click For Pricing

    VRBO

    Spectacular Vineyard Setting in Watermill

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    6

    Private and serene setting on a cul-de-sac backing directly onto a wine vineyard offers 4 bedrooms and 2.5 baths. This c ...

    Click For Pricing

    VRBO

    Details
  • Idyllic views in Water Mill with pool and tennis
    From $2257 per night (USD)

    VRBO

    Idyllic views in Water Mill with pool and tennis

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    11

    *** Please note 2-week minimum stay *** Idyllic 1.5 acre property with tennis and pool south of the highway in Water ...

    From $2257 per night (USD)

    VRBO

    Details
  • Amazing Hampton's Styled Getaway
    From $1771 per night (USD)

    VRBO

    Amazing Hampton's Styled Getaway

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    14

    This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the ...

    From $1771 per night (USD)

    VRBO

    Details
  • Beautiful home with private pool, hot tub, gym, pool table, ping pong, fire...
    From $1740 per night (USD)

    VRBO

    Beautiful home with private pool, hot tub, gym, pool table, ping pong, fire...

    Bedrooms:
    8
    Bathrooms:
    8
    Sleeps:
    16

    Please note that a reservation for this property needs to be approved before it is confirmed. Water Mill Towd Terrific ...

    From $1740 per night (USD)

    VRBO

    Details
  • Secluded Kid friendly Hampton’s home
    From $1588 per night (USD)

    VRBO

    Secluded Kid friendly Hampton’s home

    Bedrooms:
    8
    Bathrooms:
    6
    Sleeps:
    8

    Beautiful kid friendly home with in-laws suite above second family room. Flat fenced in backyard with new pool. wake up ...

    From $1588 per night (USD)

    VRBO

    Details
  • Ultimate Water Mill Southampton Escape– Stunning 7BR Estate for Family & Friends
    From $4957 per night (USD)

    VRBO

    Ultimate Water Mill Southampton Escape– Stunning 7BR Estate for Family & Friends

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    A stunning 7-bedroom, 7-bathroom estate designed for multigenerational family gatherings and friend retreats. This stunn ...

    From $4957 per night (USD)

    VRBO

    Details
  • Hamptons Escape
    From $2295 per night (USD)

    VRBO

    Hamptons Escape

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    6

    Experience luxury at its finest in this stunning retreat house located in the heart of Southampton/Watermill Horse Count ...

    From $2295 per night (USD)

    VRBO

    Details
  • Hampton Beach Barn w\/ Infrared Sauna and Heated Pool - Dog friendly.
    From $1459 per night (USD)

    Expedia

    Hampton Beach Barn w\/ Infrared Sauna and Heated Pool - Dog friendly.

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    3,000sf (approximate) Post & Beam Beach Barn, located in the upscale hamlet of Water Mill in Southampton, NY. POOL OP ...

    From $1459 per night (USD)

    Expedia

    Details
  • NEW LISTING : SOUTHAMPTON PRIVATE HOME!!
    Click For Pricing

    VRBO

    NEW LISTING : SOUTHAMPTON PRIVATE HOME!!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful Southampton home with 4 bedrooms and 3 full baths! Private one acre lot backing to a preserve area. Home has ...

    Click For Pricing

    VRBO

    Details
  • Water Mill Perfection: Tennis, Saltwater Pool, Winery, Art Museum, Kids Oasis
    From $2620 per night (USD)

    Expedia

    Water Mill Perfection: Tennis, Saltwater Pool, Winery, Art Museum, Kids Oasis

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    14

    This one of a kind property runs against the backside of Duckwalk Vineyards and is just a short 5-minute walk to wine ta ...

    From $2620 per night (USD)

    Expedia

    Details
  • Heated Pool and Tennis Court
    From $3047 per night (USD)

    VRBO

    Heated Pool and Tennis Court

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Gorgeous like new condition open-floor plan home in the heart of the Hamptons. Close to everything; Flying Point Beach, ...

    From $3047 per night (USD)

    VRBO

    Details
  • Like Tuscany, private Vineyard Home, Southampton
    From $1314 per night (USD)

    VRBO

    Like Tuscany, private Vineyard Home, Southampton

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    7

    Like Tuscany, truly surrounded by vineyards. Gorgeous views from every room. Open concept kitchen, travertine floors, hi ...

    From $1314 per night (USD)

    VRBO

    Details
  • Beautiful, Spacious, Private, Family- Friendly Home In Water Mill (4000 SF)
    From $2394 per night (USD)

    VRBO

    Beautiful, Spacious, Private, Family- Friendly Home In Water Mill (4000 SF)

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Enjoy over 60 acres of protected farmfield vistas from this charming and recently renovated 5-bedroom Hampton home. Priv ...

    From $2394 per night (USD)

    VRBO

    Details
  • Six Bedroom Designer Home Southhampton
    From $4072 per night (USD)

    VRBO

    Six Bedroom Designer Home Southhampton

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    10

    Summary: This custom home sits on 0.60 of an acre and features 3,800 + square feet with 5 bedrooms, five full baths and ...

    From $4072 per night (USD)

    VRBO

    Details
  • Beautiful Waterfront Condo
    Click For Pricing

    VRBO

    Beautiful Waterfront Condo

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Spacious 3 BR 3.5 Bath with large dining space, A/V in all rooms and deck, and easy access to all Water Mill, Southampto ...

    Click For Pricing

    VRBO

    Details
  • Watermill Farm Views Offer Great Spot For Family
    Click For Pricing

    Expedia

    Watermill Farm Views Offer Great Spot For Family

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Well-appointed 2-story Watermill home with spectacular farm views, breathtaking sunsets, pool, sizeable yard, and CedarW ...

    Click For Pricing

    Expedia

    Details
  • Contemporary Southampton Villa
    From $2795 per night (USD)

    VRBO

    Contemporary Southampton Villa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Situated just shy of 2 acres and home set on a rise at the end of a 400ft winding driveway, within minutes from local sh ...

    From $2795 per night (USD)

    VRBO

    Details
  • Stunning 5 bedroom Vicente Wolf Designed Home South of Highway in Water Mill
    From $2882 per night (USD)

    VRBO

    Stunning 5 bedroom Vicente Wolf Designed Home South of Highway in Water Mill

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    8

    Introducing a luxurious 5,000 sq ft modern ranch nestled on a highly sought-after private lane in Water Mill South. Th ...

    From $2882 per night (USD)

    VRBO

    Details
  • 9 Bedroom Water Mill Estate
    From $6093 per night (USD)

    VRBO

    9 Bedroom Water Mill Estate

    Bedrooms:
    13
    Bathrooms:
    9
    Sleeps:
    16

    Luxurious 13,000 square foot estate features 9 bedrooms and12.5 baths in the heart of Water Mill farmlands. All bedrooms ...

    From $6093 per night (USD)

    VRBO

    Details
  • Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
    From $579 per night (USD)

    Expedia

    Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Enjoy a vacation away in this one-level, 4-bedroom, 2-bathroom well decorated beachy cottage, just minutes from the Hamp ...

    From $579 per night (USD)

    Expedia

    Details
  • Water Mill wonderful farm house
    From $1432 per night (USD)

    VRBO

    Water Mill wonderful farm house

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Enjoy your summer in this fabulous Water Mill farm house, close to the village and beaches. The two story main house fea ...

    From $1432 per night (USD)

    VRBO

    Details
  • 1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.
    From $1048 per night (USD)

    Expedia

    1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Stay at one of the last remaining 1940s fisherman's cottages, perfectly restored on a private and secluded property. Clo ...

    From $1048 per night (USD)

    Expedia

    Details
  • Villa Emery
    From $2368 per night (USD)

    VRBO

    Villa Emery

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    7

    Experience Luxury at Villa Emery in Suffolk County Escape to Villa Emery, a luxurious retreat nestled in the serene lan ...

    From $2368 per night (USD)

    VRBO

    Details
  • Water Mill, charming country cottage
    From $413 per night (USD)

    VRBO

    Water Mill, charming country cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This cozy cottage is part of a wonderful compound in Water Mill. The cottage features a living room, a bright and light ...

    From $413 per night (USD)

    VRBO

    Details
  • Think Big Blue Skies, 4 Bedroom, 4 Bath Water Mill
    From $767 per night (USD)

    VRBO

    Think Big Blue Skies, 4 Bedroom, 4 Bath Water Mill

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    This rental doesn't come on the market very often, as usually leases turn into long term leases. Next availability star ...

    From $767 per night (USD)

    VRBO

    Details
  • Charming 3-bedroom barn house on 1-acre in Water Mill w\/ Fireplace, WiFi, W\/D
    From $290 per night (USD)

    Expedia

    Charming 3-bedroom barn house on 1-acre in Water Mill w\/ Fireplace, WiFi, W\/D

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Located in Water Mill, this charming barn house locate don 1 acre bordering and overlooking 100 acres of preserve farm f ...

    From $290 per night (USD)

    Expedia

    Details
  • 12,000 sq ft of Luxury, Modern Design, Full Gym, Indoor and Outdoor Dining...
    From $30773 per night (USD)

    VRBO

    12,000 sq ft of Luxury, Modern Design, Full Gym, Indoor and Outdoor Dining...

    Bedrooms:
    10
    Bathrooms:
    8
    Sleeps:
    6

    Please note that a reservation for this property needs to be approved before it is confirmed. Cobb Road Daydream 12,00 ...

    From $30773 per night (USD)

    VRBO

    Details