Homes for Rent near The Hayground School

• 

  

  

  /31

  $250,000 per month

  • 9 Beds
  • 8.5 Baths
  • 9,000 Sq Ft
  • House for Rent

  70 Winding Way, Water Mill, NY 11976

  May 19 - July 13 - $250,000 / June $150,000 / July 1 - July 14 - $125,000 Welcome to this stunning 9,000 sq. ft. villa in Southampton, ideally located on a quiet street and tranquil cul-de-sac in Water Mill, overlooking a beautiful vineyard. This luxurious home provides an exceptional lifestyle with 9 bedrooms and 8.5 bathrooms, making it the perfect retreat for those seeking a lavish

  Charisse Chassen Brown Harris Stevens Hamptons

  70 Winding Way, Water Mill, NY 11976
• 

  

  

  /18

  $55,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  76 Harbor Dr, Sag Harbor, NY 11963

  Welcome to your perfect newly renovated summer sanctuary in Baypoint, one of Sag Harbor's most sought-after waterfront enclaves. Just a short stroll to Foster Memorial Beach and a breezy bike ride from the charm of Sag Harbor Village, this 3-bedroom, 3.5-bath home offers everything you need for a truly unforgettable summer. Launch paddle boards and kayaks from your private deep-water dock, then

  76 Harbor Dr, Sag Harbor, NY 11963
• 

  

  

  /17

  $15,000 per month

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • House for Rent

  112 Laurel Valley Dr, Sag Harbor, NY 11963

  Welcome to beautiful 112 Laurel Valley Drive, your destination to enjoy all that Sag Harbor has to offer. This is also a perfect launch pad to explore Southampton, Bridgehampton, some of the worlds best ocean and bay beaches, shops and the restaurants that The Hamptons are known for. Majestically set upon a hill, this home provides a private back yard with a heated in-ground pool that is a

  Robert Wilner Douglas Elliman Real Estate

  112 Laurel Valley Dr, Sag Harbor, NY 11963
• 

  

  

  /20

  $150,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  55 Hildreth Ln, Bridgehampton, NY 11932

  Light, bright and breezy, this Bridgehampton vacation house offers three bedrooms, two brand new modern baths and gorgeous renovated kitchen. Featuring both privacy and convenience, the home contains a light and bright cathedral ceiling great room opening onto a south-facing deck overlooking a lushly landscaped yard with heated pool and bluestone surround. The principle bedroom also opens

  55 Hildreth Ln, Bridgehampton, NY 11932
• 

  

  

  /36

  $70,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  43 Greenleaf Ln, Sagaponack, NY 11962

  Sagaponack? 2 Cleared Acres? Tennis? So Close to the Beach?YES! It's all TRUE! Situated in Sagaponack on a quiet lane near Wolffer Estates, and around the corner from Poxabogue Golf Center (great 9 hole public course, driving range, private lessons), this four-bedroom English-country traditional estate boasts professional landscaping, jacuzzi, heated pool, sunken tennis court and meticulously

  Julie Pinkwater Douglas Elliman Real Estate

  43 Greenleaf Ln, Sagaponack, NY 11962
• 

  

  /20

  $70,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  18 Rysam St, Sag Harbor, NY 11963

  Spend July and August immersed in the magic of Sag Harbor Village, where sun-drenched days and starlit nights unfold against the stunning backdrop of marina views. This rare Captain's Row gem, a beautifully appointed 3-bedroom home, offers the perfect blend of historic charm and modern luxury. Wake up to the gentle hum of the harbor, just steps from the marina, and the village's most beloved

  18 Rysam St, Sag Harbor, NY 11963
• 

  

  /22

  $25,000 per month

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft
  • House for Rent

  20 Hildreth St, Sag Harbor, NY 11963

  **Charming Summer Retreat in Sag Harbor**Escape to the picturesque charm of Sag Harbor with this delightful summer rental, perfectly situated just a stone's throw from the vibrant village. This inviting home offers three spacious bedrooms and a bonus spaceThe property features 1.5 bathrooms and is equipped with air conditioning to ensure your comfort during those warm summer days.

  Bridget Terry Compass Greater NY LLC

  20 Hildreth St, Sag Harbor, NY 11963
• 

  

  /20

  $85,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  11 Henry St, Sag Harbor, NY 11963

  Graceful and beautiful 1830 Greek Revival home on .22 acres, and once the first Presbyterian parsonage, is where old charm still abounds! Although there are modern updates such as central air, many of the original details, including timeless pocket doors, wide plank wood flooring, and five fireplaces, are preserved. The original front door welcomes you into the classic living room with fireplace

  11 Henry St, Sag Harbor, NY 11963
• 

  

  /27

  $40,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  61 Peconic Ave, Sag Harbor, NY 11963

  Envision your perfect summer unfolding in this exquisite and expansive residence nestled within Shelter Island’s prestigious Silver Beach area. Recently completely renovated from the ground up in 2024, this home boasts a captivating blend of elegance and modernity. Step inside to discover a meticulously designed floor plan featuring dual primary suites, one conveniently located on the ground

  Michael Brennan Douglas Elliman Real Estate

  61 Peconic Ave, Sag Harbor, NY 11963
• 

  

  /18

  $48,000 per month

  • 2 Beds
  • 2 Baths
  • House for Rent

  10 Leland Ln, Southampton, NY 11968

  This Southampton Village condo located at Canterbury Mews Association has so much to offer. Spacious and filled with sun this two-bedroom two -bath end unit is just moments from Hampton's ocean beaches, and the Village's shopping and dining. In addition to the premier location, the Canterbury Mews Association also offers two community tennis courts, pickleball court and heated salt water

  10 Leland Ln, Southampton, NY 11968
• 

  

  /47

  $350,000 per month

  • 12 Beds
  • 11 Baths
  • 5,800 Sq Ft
  • House for Rent

  179 Montauk Hwy, East Hampton, NY 11937

  Sleek Modern Retreat with Luxury AmenitiesThis stunning contemporary home offers 5,800± sq. ft. of impeccably designed living space with five bedrooms and six full baths. Thoughtfully designed for comfort and accessibility, the home is handicap-friendly, featuring wide entryways, an open layout, and a first-floor primary suite to ensure ease of movement throughout. Walls of glass, custom

  Angela Boyer Sothebys Int'l Realty Hamptons

  179 Montauk Hwy, East Hampton, NY 11937
• 

  

  /9

  $35,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  16 Fordham St, Sag Harbor, NY 11963

  Tucked away on a quiet street in Sag Harbor Village, this charming Cape Cod home offers easy access to Main Street's shops, restaurants, and waterfront. The simple and welcoming layout features three bedrooms and two full bathrooms, with comfortable living spaces that feel instantly inviting. Outdoors, enjoy a peaceful backyard perfect for summer afternoons. A wonderful opportunity to experience

  16 Fordham St, Sag Harbor, NY 11963
• 

  

  /16

  $48,000 per month

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • House for Rent

  51 Tansey Ln, Bridgehampton, NY 11932

  Spend your summer in this newly renovated four bedroom, three bathroom plus home office. This home is perfect for summer entertaining with family and friends and lies conveniently between Bridgehampton and Sag Harbor on a quite street. Set on a half acre +/- of privately landscaped grounds, which backs up to a nature reserve. The modern, upgraded kitchen boasts granite countertops and stainless

  Toni Asch Douglas Elliman Real Estate

  51 Tansey Ln, Bridgehampton, NY 11932
• 

  

  /17

  $75,000 per month

  • 3 Beds
  • 4 Baths
  • House for Rent

  37 Potato Field Ln, Southampton, NY 11968

  Rent this stunning gut-renovated condo in Southampton Village! This modern-designed property offers a luxurious living experience with its three bedrooms, two full baths, and two half baths. The main floor features an open concept floor plan, showcasing a high-end kitchen with chef-like appliances and a kitchen island with barstool seating. The focal point of the living area is a stunning gas

  37 Potato Field Ln, Southampton, NY 11968
• 

  

  /15

  $20,000 per month

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft
  • House for Rent

  3389 Noyac Rd, Sag Harbor, NY 11963

  Beautifully and recently renovated ranch home near Circle beach in Noyac with vaulted ceilings, open kitchen, TV room, 2 renovated bathrooms, central air, just about everything you need before you head to the beach! Close to Sag Harbor, Long Beach, restaurants and marinas. Just reduced for July at $20,000. Also available for June at $12,000.

  Robert Florio Daniel Gale Sothebys Intl Rlty

  3389 Noyac Rd, Sag Harbor, NY 11963
• 

  

  /20

  $120,000 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  7 Fairway Ct, Sag Harbor, NY 11963

  Discover your dream retreat in the heart of Sag Harbor. Set on a private 2.3 +/- acre lot in an exclusive neighborhood, this pristine 3,300 +/- sq. ft. home offers 4 bedrooms, 3 baths, and a detached 2-car garage. The bright, open interior boasts a custom gourmet kitchen flowing seamlessly into the living and dining areas, highlighted by a stunning two-story Westchester Granite fireplace and

  7 Fairway Ct, Sag Harbor, NY 11963
• 

  

  /30

  $40,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  17 Bay View Rd W, Southampton, NY 11968

  RP241487. Located in Bayview Oaks, a Southampton waterfront community with its own access to Peconic Bay. Bright and airy with an open floor plan, this custom built home with high-end designer furnishings offers 4 bedrooms, plus a large bunk room and 3.5 bathrooms. Living room with fireplace, dining room and gourmet eat-in kitchen have 13+ foot ceilings. With the master bedroom on one side, bunk

  John Vitello Brown Harris Stevens Hamptons

  17 Bay View Rd W, Southampton, NY 11968
• 

  

  /20

  $127,000 per month

  • 5 Beds
  • 5 Baths
  • House for Rent

  23 Winding Way, Water Mill, NY 11976

  This beautiful living space just had a full high end renovation including light oak floors, new lighting fixtures thruout, new bathrooms, an Italian Kitrchen, open large living room with fireplace and a separate media room. This 3300 square feet of living space includes 5 bedrooms, 4.5 baths, a master suite, a guest suite and 3 more bedrooms. This is one level living and entertainment at its

  23 Winding Way, Water Mill, NY 11976
• 

  

  /18

  $75,000 per month

  • 7 Beds
  • 8 Baths
  • 6,995 Sq Ft
  • House for Rent

  520 Water Mill Towd Rd, Southampton, NY 11968

  This beautiful home offers great style and large open space and all amenities. Open cathedral living room with fireplace, Huge kitchen with center island and stools for the 'in the kitchen parties", open dining room with fireplace, screened in porch for summer entertaining. The kitchen, dining room, living room and screened porch all connected. All very large public rooms plus a large first floor

  Trudy Pereira Brown Harris Stevens Hamptons

  520 Water Mill Towd Rd, Southampton, NY 11968
• 

  

  /14

  $29,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  37 Wainscott Rd NW, Wainscott, NY 11975

  Rental Registration #: 20-1,099 Bright and beautiful traditional home at 37 Wainscott Northwest Road is on one-acre flag lot in Wainscott south. First-floor master suite with fireplace, opening to mahogany decks and heated pool. There are 3 additional bedrooms and baths, den, elegant driveway approach and beautiful landscaping. The shores of the Atlantic await 37 Wainscott Northwest Road at

  37 Wainscott Rd NW, Wainscott, NY 11975
• 

  

  /25

  $40,000 per month

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • House for Rent

  8 Dovas Path, Southampton, NY 11968

  This enchanting three bedroom/two bathroom summer rental in Southampton offers a luxurious, private escape on 1.3 manicured acres and just minutes from the Village center. Nestled on a quiet cul-de-sac among other upscale homes, the property features stunning gardens and an elegant, open-concept living space. With a modern kitchen, quartz countertops, a dining area which seats ten and a second

  Nancy Pearson Sothebys Int'l Realty Hamptons

  8 Dovas Path, Southampton, NY 11968
• 

  

  /14

  $60,000 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  16 Magnolia Dr, Water Mill, NY 11976

  Discover the epitome of modern Hamptons living in this newly completed 4-bedroom, 4-bath townhouse at Watermill Crossing. Designed for those who value both style and function, the main level features an expansive great room seamlessly connected to a sleek chef's kitchen with porcelain countertops and high-end appliances. A versatile den on this level doubles as your fourth bedroom, guest suite,

  16 Magnolia Dr, Water Mill, NY 11976
• 

  

  /26

  $155,000 per month

  • 6 Beds
  • 8 Baths
  • 5,800 Sq Ft
  • House for Rent

  262 Roses Grove Rd, Water Mill, NY 11976

  WATER MILL HILLTOP WITH POOL AND TENNS This spacious two-story traditional is located privately and secluded on a landscaped 2.10-acre property in Water Mill. The home boasts a spacious living and dining room overlooking the backyard. A professional eat-in kitchen with breakfast are leads to the back bluestone patio for outdoor dining and lounging. The main floor also has a generous junior

  Trudy Pereira Brown Harris Stevens Hamptons

  262 Roses Grove Rd, Water Mill, NY 11976
• 

  

  /16

  $55,000 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  41 Rawson Rd, Sag Harbor, NY 11963

  This beautiful 4 bedroom home in a special bayfront enclave in Sag Harbor is steps away from the residents-only beach. Spacious 4 bedrooms and 3.5 baths on an acre of manicured grounds, with immense outdoor space for summer entertaining - think pool parties, afternoon barbeques, and dinner parties under the summer stars. Open floor plan includes eat-in kitchen, light-filled, two-story great room

  41 Rawson Rd, Sag Harbor, NY 11963
• 

  

  /36

  $50,000 per month

  • 2 Beds
  • 2 Baths
  • 2,197 Sq Ft
  • House for Rent

  1 Burkeshire Dr, Sag Harbor, NY 11963

  Soak up the perfect Hamptons summer in Sag Harbor w/ your very own private spa experience. The sunny pool house featuring a gunite pool, yoga deck and sauna will melt your cares away upon your arrival, after a day at the beach or after a day strolling through downtown Sag Harbor. The primary bedroom features vaulted ceilings, a skylight, a ceiling fan a king size bed and in wall speakers. The

  Zachariah Zaleski Douglas Elliman Real Estate

  1 Burkeshire Dr, Sag Harbor, NY 11963
• 

  

  /20

  $110,000 per month

  • 5 Beds
  • 7 Baths
  • House for Rent

  260 Halsey Ln, Bridgehampton, NY 11932

  Experience a breathtaking summer in this brand new south-of-the-highway home. This fully furnished rental features a spacious living room with fireplace, open dining room for 12 and eat-in kitchen that was literally designed by a chef. The first floor is complete with a guest suite, powder room, and mudroom leading to the attached garage. Upstairs, two guest suites accompany the gorgeous primary

  260 Halsey Ln, Bridgehampton, NY 11932
• 

  

  /27

  $25,000 per month

  • 3 Beds
  • 2 Baths
  • 10,890 Sq Ft
  • House for Rent

  46 Bayview Ave, Sag Harbor, NY 11963

  This is an amazing opportunity to enjoy everything that Sag Harbor Village can offer. This home is close to beautiful marinas, world-wide restaurants, and beaches, just a few minutes from Jitney and Main Street. This home features three bedrooms, two baths, a hot tub, a big backyard, a pool, inviting decor, a spacious living area with a fireplace, and a fully equipped kitchen ready for your

  Elizabeth Cordova Alata Douglas Elliman Real Estate

  46 Bayview Ave, Sag Harbor, NY 11963
• 

  

  /20

  $70,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  17 Elisha's Path, Wainscott, NY 11975

  Experience the epitome of modern luxury in this impeccable 5-bedroom, 5.5-bath home nestled on 1.4 private acres at the end of a tranquil cul-de-sac in Wainscott. Abutting a $9M estate, this fully renovated residence offers 5,000+ sq. ft. of elegant living space, including expansive open-concept interiors bathed in natural light. The soaring double-height great room with a striking fireplace,

  17 Elisha's Path, Wainscott, NY 11975
• 

  

  /31

  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 1,848 Sq Ft
  • House for Rent

  15 Mount Misery Dr, Sag Harbor, NY 11963

  Indulge in Design: Hamptons Summer Rental Experience the magic of Sag Harbor Village has to offer in this charming Hamptons Designer Retreat just moments from Heavens beach-Indulge in design and sophistication in this Hamptons summer rental. Nestled in the charming enclave of Sag Harbor Village, experience world-class dining, art galleries, and a vibrant cultural scene of stunning natural

  Elizabeth Cordova Alata Douglas Elliman Real Estate

  15 Mount Misery Dr, Sag Harbor, NY 11963
• 

  

  /20

  $195,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  40 Poxabogue Pond Rd, Sagaponack, NY 11937

  Escape to this serene Sagaponack home, perfectly located just moments from world-class beaches, golf courses, and renowned wineries. Set on nearly two acres with over 200 feet of private pond frontage, this home offers breathtaking water views and ultimate tranquility, bordered by a 17-acre agricultural reserve. Inside, the main floor features a spacious eat-in kitchen with a fireplace, a

  40 Poxabogue Pond Rd, Sagaponack, NY 11937
• 

  

  /44

  $100,000 per month

  • 5 Beds
  • 5.5 Baths
  • 3,456 Sq Ft
  • House for Rent

  Unlisted Address

  Every detail of this stunning home has been thoughtfully designed to offer a luxurious and peaceful escape in the heart of the Hamptons. Located just minutes from the charming Sag Harbor Village and Bridgehampton, the property is perched on a rise, providing rare, lovely water vistas of Noyac Bay from its rooftop living platform. This five-bedroom, five-and-a-half-bathroom masterpiece is tailored

  Joseph Van Asco Douglas Elliman Real Estate

  Unlisted Address
• 

  

  /20

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • House for Rent

  78 Northview Hills Ct, Sag Harbor, NY 11963

  Enjoy summer in this private, beautiful home minutes to the bay beach and Sag Harbor. Wonderful landscaping provides a serene setting for you to enjoy lying by the pool [[Rental Registration # RP240387]]

  78 Northview Hills Ct, Sag Harbor, NY 11963
• 

  

  /48

  $300,000 per month

  • 6 Beds
  • 5 Baths
  • 2,900 Sq Ft
  • House for Rent

  371 Route 114, East Hampton, NY 11937

  Your Dream Hamptons Retreat: 6 Bedrooms, Pool and Tennis CourtEmbrace the Hamptons lifestyle at this stunning, luxurious, spacious sanctuary, a 6-bedroom, 5-bathroom private paradise. Drive up the long, winding driveway into 4 acres of professionally, breathtakingly landscaped gardens and secluded woods. The spacious and sun-kissed Serenity interior boasts modern amenities and stylish

  Elizabeth Cordova Alata Douglas Elliman Real Estate

  371 Route 114, East Hampton, NY 11937
• 

  

  /25

  $85,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  221 Division St, Sag Harbor, NY 11963

  Welcome to 221 Division Street-an exceptional summer retreat in the very heart of Sag Harbor Village. This historic cottage has been completely re-envisioned with a refined touch, blending timeless character with a chic, mid-century modern sensibility. Thoughtfully designed to offer both sophistication and comfort, the home features two distinct living rooms, perfect for relaxing or entertaining,

  221 Division St, Sag Harbor, NY 11963
• 

  

  /28

  $85,000 per month

  • 7 Beds
  • 7.5 Baths
  • 6,000 Sq Ft
  • House for Rent

  2 Hannahs Ct, Southampton, NY 11968

  This 6000 s/f above ground beautiful 2018 construction is located on one landscaped acre on a quiet cul-de-sac and conveniently located minutes from Southampton Village, Beaches, Southampton Recreation Center and the Peconic Bay. The first floor has a large eat-in kitchen with sub-zero/thermador appliances and a beautiful center island with French doors that lead to an outdoor partially covered

  Lillian Holtzclaw Brown Harris Stevens Hamptons

  2 Hannahs Ct, Southampton, NY 11968
• 

  

  /26

  $125,000 per month

  • 3 Beds
  • 3 Baths
  • House for Rent

  299 Main St, Sag Harbor, NY 11963

  Looking for a spacious rental in the village of Sag Harbor? Experience Sag Harbor Cove sunset views from this versatile village home and cottage retreat filled with character and comfort. Situated on Main Street, just moments from the heart of Sag Harbor, this spacious home is convenient to shopping, restaurants and the Hampton Jitney. Inside the main house, a bright foyer opens to a classic

  299 Main St, Sag Harbor, NY 11963
• 

  

  /48

  $275,000 per month

  • 7 Beds
  • 6.5 Baths
  • 7,800 Sq Ft
  • House for Rent

  28 Kendalls Ln, Southampton, NY 11968

  In Southampton at the end of a private road sits KISMET, a modern waterfront oasis prominently situated on Wooley Pond with open access to Peconic Bay. Also offers your own boat dock for all your water recreation. Built by the expert team of Cavallo Building, renowned Hamptons architect Siyu Liu, and designed by award-winning Suzanne Kelley, this new construction boasts 7,800 square feet with

  Thomas Cavallo Douglas Elliman Real Estate

  28 Kendalls Ln, Southampton, NY 11968
• 

  

  /20

  $80,000 per month

  • 3 Beds
  • 3 Baths
  • House for Rent

  45 Cosdrew Ln, East Hampton, NY 11937

  Newly renovated in 2021, your luxurious summer sanctuary awaits just moments to Sag Harbor and East Hampton villages. The bright open floor plan features an eat-in kitchen and living room with vaulted ceilings and a gas fireplace for those cool summer nights, plus a lower-level gym to keep in summer shape. Enjoy time in the office/reading nook or the pool in the privacy of the backyard on the

  45 Cosdrew Ln, East Hampton, NY 11937
• 

  

  /20

  $165,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft
  • Condo for Rent

  520 Hampton Rd Unit 18, Southampton, NY 11968

  EXQUISITE SOUTHAMPTON VILLAGE CONDO RENTAL!Be the first to rent this spectacular fully renovated, designer decorated, 3 bedroom 3.5 bathroom Southampton Village home located in Farrington Close. This unit is approximately 2300+/-sqft. The open floor plan has multiple entertaining spaces including a living room, dining and a top of the line gourmet eat-in kitchen. Additionally, there are 3

  Toni Asch Douglas Elliman Real Estate

  520 Hampton Rd Unit 18, Southampton, NY 11968
• 

  

  /29

  $75,000 per month

  • 6 Beds
  • 5 Baths
  • House for Rent

  2 Fair Hills Ln, Bridgehampton, NY 11932

  Discover the epitome of modern farmhouse living in this brand-new Bridgehampton estate, set on nearly an acre of beautifully manicured grounds. Spanning more than 6500SF, this 6-bedroom, 4.5-bath home is has a wow factor combined with effortless comfort. At its heart is a spectacular chef's kitchen, outfitted with top-of-the-line appliances, custom cabinetry, and an inviting breakfast nook.

  2 Fair Hills Ln, Bridgehampton, NY 11932

Showing Results 41 - 80, Page 2 of 8